Синтез функционально замещенных алкенов и гетероциклических соединений на основе реакции каталитического олефинирования
Диссертация
Гидроксиламин. Синтез изоксазолов. Амиды гидроксамовых кислот. Получение 2-хлор-И'-гидрокси-3-арилакриламидинов. Список литера туры. Реакции активированных галогенолефинов, приводящие к построению карбоциклов. Дибромацетонитрил. Синтез нитрилов коричных кислот. ОБСУЖДЕНИЕ РЕЗУЛЬТАТОВ2. 1. Синтез функционально замещенных алкенов по реакции каталитического олефинирования2. 1. 1. Этилтрихлорацетат… Читать ещё >
Список литературы
- Preparation of Alkenes // Ed. Williams J. M. J. Oxford: Oxford University Press. 1996. 254 c.
- Smith A.B. Ill, Branca S.J., PillaN.N., GuaciaroM.A. Stereocontrolled total synthesis of (±)-pentenomycins I-III, their epimers, and dehydropentenomycin I // J. Org. Chem. -1982.-Y. 47, № 10.-P. 1855−1869.
- Dunn G.L., DiPasquo V.J., Hoover J.R.E. Synthesis of pentacyclo4.3.0.02,5.02,8.04,7.-nonane (homocubane) and some of its derivatives // J. Org. Chem. 1968. — V. 33, № 4. -P. 1454−1459.
- Bordwell F.G., Wellman K.M. Dehydrobromination of cw-2,6-dibromo-4,4-dimethylcyclohexanone and of c/s-2,6-dibromo-4,4-diphenylcyclohexanone // J. Org. Chem. -1963. V. 28, № 10. — P. 2544−2550.
- Schollberg K., Schafer H., Gewald K. Vereinfachte Darstellung von a-Chlor- und P-Chlor-a-cyanzimtsdurenitrilen // J. Prakt. Chem. -1983. B. 325. — P. 876−879.
- Пастушак H.O., Домбровский A.B., Роговик Л.И. XIX Хлорарилирование а-хлоракрилонитрила И ЖОХ. -1964. Т. 34, вып. 7. — С. 2243−2246.
- JahnischK., SeebothH. Synthesen von p-Fur-2-yl-a-halogenacrylOnitrilen // J. Prakt. Chem. -1981. B. 323. — P. 26−32.
- Wender P.A., Hillemaun C.L., Szymonifka M.J. An approach to the tiglianes, daphnanes and ingenanes via the divinylcyclopropane rearrangement // Tetrahedron Lett. 1980. -V.21, № 23. — P. 2205−2208.
- Smith A.B. Ill, Branca S.J., Guactaro M.A., Wovkulich P.M., Korn A. // Org. Synth. Coll. V. 7. — New York: John Wiley & Sons Inc., 1990. — P. 271.
- KamigataN., Satoh Т., Yoshida M. Reaction of benzeneseleninyl chloride with olefins in the presence of a Lewis acid. A novel one step vinylic chlorination // Bull. Chem. Soc. Jpn. -1988. V. 61, № 2. — P. 449−454.
- Li W., Li J., Wan Z.-K., Wu J., Massefski W. Preparation of a-Haloacrylate Derivatives via Dimethyl Sulfoxide-Mediated Selective Dehydrohalogenation // Org. Lett. 2007. — V. 9, № 22.-P. 4607−4610.
- SaoudiA., HamelinJ., BenhaouaH. Elimination reaction over solid supports under microwave irradiation: Synthesis of functionalized alkenes // Tetrahedron Lett 1998. — V. 39, № 23.-P. 4035−4038.
- Hamelin J., Saoudi A., Benhaouab H. Versatile transformations of a, P-dibromoesters and ketones in basic media under microwave irradiation // Synthesis. 2003. — № 14. — P. 21 852 188.
- BoseG., Bujar BaruaP.M., Chaudhuri M.K., KalitaD., KhanA.T. A convenient and useful method of preparation of a-bromo enones from the corresponding enones using organic ammonium tribromide (OATB) // Chem. Lett. 2001. — V. 30, № 4. — P. 290−291.
- Dauben W.G., Warshawsky A.M. Synthesis of functionalized a-bromo-a, p-cyclopentenones // Synth. Commun. -1988. -V. 18, № 12. P. 1323−1326.
- Ваккег B.H., Chow Y.L. The electrophilic addition of dimethylbromosulfonium bromide to conjugated enones: efficient synthesis of a-bromo enones // Can. J. Chem. 1982. — V. 60.-P. 2268−2273.
- Joo Y.H., Kim J.K., Kang S. A convenient synthesis of 3-bromoflavones // Synth. Commun. 2002. — V. 32, № 11. — P. 1653−1658.
- Amice P., Blanco L., Conia J.M. Enol silyl ethers and their use for the synthesis of a-halo-a,{3-unsaturated carbonyl compounds // Synthesis. -1976. № 3. — P. 196.
- HoT.-L., Gupta B.G.B., Olah G.A. Phase transfer catalyst promoted halogenation of alkenes with hydrohalic acid/hydrogen peroxide // Synthesis. -1977. № 10. — P. 676.
- Dieter R.K., Nice L.E., Velu S.E. Oxidation of a, P-enoncs and alkenes with oxone and sodium halides: A convenient laboratory preparation of chlorine and bromine // Tetrahedron Lett. 1996. — V. 37, № 14. — P. 2377−2380.
- Kim K.M., Chung K.H., Kim J.N., Ryu E.K. A facile synthesis of a-chloro enones by oxidative chlorination // Synthesis. -1993. № 3. — P. 283−284.
- Chen S., Wang J. One-Pot Synthesis of a-Iodo-Substituted-a, p-Unsaturated Aldehydes from Propargylic Alcohols. // J. Org. Chem. 2007, — V.72, № 13. — P. 4993−4996.
- Kim K.-M., Park I.-H. A convenient halogenation of a, p-unsaturated carbonyl compounds with OXONE® and hydrohalic acid (HBr, HC1) // Synthesis. 2004. — № 16. — P. 26 412 644.
- Kim K.K., Kim J.N., Kim K.M., Kim H.R., Ryu E.K. One-pot synthesis of a, a-dichloroketones from alkynes using the N, N-dimethylformamide/HCl/potassium monoperoxysulfate system // Chem. Lett. 1992. — V. 21, № 4. — P. 603−604.
- Chung K.H., Kim K.M., Kim J.N., Ryu E.K. Oxidative chlorination of acetanilides with hydrogen chloride/m-chloroperbenzoic acid/N, N-dimethylformamide system // Synth. Commun.- 1991.-V. 21, № 18−19.-P. 1917−1922.
- Furness M.S., Robinson T.P., Goldsmith D.J., Bowen J.P. An efficient synthesis of 2-aryl and 2-alkenyl-3-alkoxy-cyclohexenones by a modified Stille reaction // Tetrahedron Lett. -1999. V. 40, № 3. — P. 459−462.
- Ramanarayanan G.V., Shukla V.G., Akamanchi K.G. A novel and one step procedure for preparation of a-bromo-a, P-unsaturated carbonyl compounds // Synlett. 2002. — № 12. — P. 2059−2061.
- Bovonsombat P., Rujiwarangkul R., Bowornkiengkai Т., Leykajarakul J. a-Bromination of linear enals and cyclic enones. // Tetrahedron Lett. 2007. — V. 48, № 49. — P. 86 078 610.
- Bovonsombat P., Angara G.J., McNelis E. Concerning the formations of a-iodoenones // Tetrahedron Lett. -1994. V. 35, № 37. — P. 6787−6790.
- Whang J.P., Yang S.G., Kim Y.H. Novel a-iodination of functionalized ketones with iodine mediated by bis (tetra-n-butylammonium) peroxydisulfate // Chem. Commun. -1997. -V. 15.-P. 1355−1356.
- Alimardanov A., Negishi E. Synthesis of a-iodo- a,(3-unsalurated ketones by the reaction of a-silyl-a, p-unsaturated ketones with IC1 or IC1—A1C13 // Tetrahedron Lett. 1999. -V.40, № 20.-P. 3839−3842.
- Johnson C.J., Adams J.P., Braun M.P., Senanayake C.B.W., Wovkulich P.M., Uskokovic M.R. Direct a-iodination of cycloalkenones // Tetrahedron Lett. 1992. — V. 33, № 7. — P. 917−918.on
- KrafftM.E., CranJ.W. A convenient protocol for the a-iodination of a, P-unsaturated carbonyl compounds with I2 in an aqueous medium // Synlett. 2005. — № 8. — P. 12 631 266.1. TO
- Righi G., Bovicelli P., Sperandio A. A mild preparation of a-halo-a, p-enones from cyclic enones // Tetrahedron Lett. 1999. — V. 40, № 32. — P. 5889−5892.
- Mandal A.K., Mahajan S.W. Novel transformations with borontrifluoride etherate/iodide ion: facile conversion of 2-ketooxiranes and 2-bromo-2-enones to the a,|3-unsaturated carbonyl compounds // Tetrahedron 1988. — V. 44, № 8. — P. 2293−2299.
- Angara G.J., McNelis E. a-Haloenones from secondary alkynols // Tetrahedron Lett. -1991.-V. 32,№ 19.-P. 2099−2100.
- QianC., ZhuD. Yttrium compounds: new catalysts for the regioselective acylative cleavage of epoxides // Synth. Commun. -1994. V. 24, № 15. — P. 2203−2214.
- KotsukiH., Shimanouchi Т., OhshimaR., Fujiwara S. Solvent-free organic reactions on silica gel supports. Facile transformation of epoxides to p-halohydrins with lithium halides // Tetrahedron. -1998. V. 54, № 12. — P. 2709−2722.
- AokiY., OshimaK., UtimotoK. Preparation of a-bromoenolates from a, a-dibromoketones with «-BuLi, PhMgBr, or Et2Zn via halogen-metal exchange reaction // Synlett. -1995. № 10. — P. 1071−1072.
- Choudary B.M., MahendarK., KantamM.L., Ranganath K.V.S., AtharT. The one-pot Wittig reaction: a facile synthesis of a, P-unsaturated esters and nitriles by using nanocrystalline magnesium oxide. // Adv. Synth. Cat. 2006. — Y. 348, № 14. — P. 19 771 985.
- Burton D.J., Greenwald J.R. The reaction of triphenylphosphine with Trihalo-Acid derivatives a convenient preparation of a-halo vinyl esters and nitriles // Tetrahedron Lett. — 1967. — V. 8, № 16. — P. 1535−1539.
- Матвеева Е.Д., ЕринА.С., Осетров А. Г., ЛещеваИ.Ф., КурцА.Л. Хемо- и стереоселективность реакции ароматических альдегидов с трифенилфосфином и производными трихлоруксусной кислоты //ЖОрХ. 2006. — Т. 42, № 3. — С. 400−404.
- Thiemann Т., Tanaka Y., Ideta К., Mataka S. Solvent reduced Wittig olefination reactions with halo containing conjugated phosphoranes. // Cent. Eur. J. Chem. 2006. — V. 4, № 3. -P. 403−427.jO
- Zoute L., Dutheuil G., Quirion J.-C., Jubault P., Pannecoucke X. Efficient synthesis of fluoroalkenes via diethylzinc-promoted Wittig reaction // Synthesis. 2006. — № 20. — P. 3409−3418.
- Chevrie D., Lequeux Т., Pommelet J.-C. /er/-Butylsulfinyl-fluoroacetate: versatile reagent for the preparation of fluoroethylidenoate derivatives II Tetrahedron. 2002. — V. 58, № 24. -P. 4759−4767.
- Zoute L., Lacombe C., Quirion J.-C., Charette A.B., Jubault P. Phosphonium supported triphenylphosphine reagent: An improved access to a-fluoro-a, p-unsaturated esters. // Tetrahedron Lett. 2006. — V. 47, № 45. — P. 7931−7933.
- Suzuki Y., Sato M. A facile one-pot synthesis of a-fluoro-a,|3-unsaturated esters from alkoxycarbonylmethyltriphenylphosphonium bromides // Tetrahedron Lett. 2004. — V. 45, № 8.-P. 1679−1681.
- Huang Z., YuX., Huang X. a-Hypervalent iodine functionalized phosphonium and arsonium ylides and their tandem reaction as umpolung reagents // J. Org. Chem. 2002. -V. 67, № 23.-P. 8261−8264.
- Yu X., Huang X. Microwave-assisted tandem nucleophilic substitution-Wittig reaction of a-hypervalent iodine functionalized phosphonium ylide // Synlett. 2002. — № 11. — P. 1895−1897.
- ChenaultJ., DupinJ.E. (Ethoxycarbonyliodomethyl)triphenylphosphonium iodide: a convenient reagent for the direct synthesis of P-substituted propiolic acids via the corresponding esters // Synthesis. -1987. № 5. — P. 498−499.
- KayserM.M., Zhu J., Hooper D.L. Stabilized haloylides: synthesis and reactivity // Can. J. Chem. -1997. V. 75.-P. 1315−1321.
- Zhang X., Zhong P., Chen F. A facile one-pot synthesis of a-iodo-a, P-unsaturated esters // Synth. Commun. 2004. — V. 34, № 9. — P. 1729−1736.
- Frattini S., Quai M., Cereda E. Kinetic study of microwave-assisted Wittig reaction of stabilized ylides with aromatic aldehydes // Tetrahedron Lett. 2001. — V. 42, № 39. — P. 6827−6829.
- Tronchet J.M.J., Martin O., Zumwald J.-B., Le-HongN., PerretF. Derives C-glycosyliques XXVI. Nouvelles voies d’acces a des C-nucleosides isoxazoliques et thiopheniques. Communication preliminaire // Helv. Chim. Acta. 1975. — V. 58, № 6. — P. 1735−1738.
- LoveyAJ., PawsonB.A. Fluorinated retinoic acids and their analogs. Synthesis and biological activity of aromatic 6-fluoro analogs // J. Med. Chem. 1982. — V. 25, № 1. — P. 71−75.
- AsatoA.E., KiniA., DennyM., LiuR.S.H. 7-Cis, 9-cis, ll-cis-Retinal, all cis-vitamin A and 7-cis, 9-cis, l l-cis-12-fluororetinal. New geometric isomers of vitamin A and carotenoids. 12 // J. Am. Chem. Soc. -1983. V. 105, № 9. — P. 2923−2924.
- Collins P.W., Kramer S.W., Gullikson G.W. Synthesis and gastrointestinal pharmacology of the 4-fluoro analog of enisoprost // J. Med. Chem. 1987. — V. 30, № 11. — P. 19 521 955.
- Thenappan A., Burton D.J. Reduction-oleflnation of esters: a new and efficient synthesis of a-fluoro-a, P-unsaturated esters II J. Org. Chem. -1990. V. 55, № 15. — P. 4639−4642.
- Tsai H.-J., Thenappan A., Burton D.J. An expedient synthesis of a-fluoro-a, p-unsaturated diesters // Tetrahedron Lett. -1992. V. 33, № 44. — P. 6579−6582.
- Patrick T.B., LanahanM.V., YangC., Walker J.K., Hutchinson C.L., NealB.E. New fluorobutenolide templates for synthesis // J. Org. Chem. 1994. — V. 59, № 5. — P. 12 101 212.
- TsaiH.-J., ThenappanA., Burton DJ. A novel intramolecular Horner-Wadsworth-Emmons reaction: A simple and general route to a-fluoro-a, p-unsaturated diesters // J. Org. Chem. -1994. V. 59, № 23. — P. 7085−7091.о
- Piva O. A short access to a-fluoro-p, Y-unsaturated esters // Synlett. 1994. — № 9. — P. 729−731.
- ShinadaT., SekiyaN., BojkovaN., YoshiharaK. Stereocontrolled functionalization at the C-9 of retinal. Stereoselective synthesis of 9-/ra/M-9-fluororetinal // Synlett. 1995. — № 12. -P. 1247−1248.
- Shen Y., Ni J. A novel sequential transformations of phosphonate. Highly stereoselective synthesis of perfluoroalkylated a-fluoro-a, P unsaturated esters // J. Org. Chem. 1997. — V. 62, № 21.-P. 7260−7262.71
- PomeislK., KvicalaJ., PaletaO. Convenient synthesis of 3-fluoro-4,5-diphenylfuran-2(5H)-one from benzoin ethers. // J. Fluorine Chem. 2006. — V. 127, № 10. — P. 13 901 397.
- Kitazume Т., Tanaka G. Preparation of fluorinated alkenes in ionic liquids // J. Fluorine Chem. 2000. — V. 106, № 2. — P. 211−215.
- Sano S., Saito K., Nagao Y. Tandem reduction-olefmation for the stereoselective synthesis of (Z)-a-fluoro-a, P-unsaturated esters // Tetrahedron Lett. 2003. — V. 44, № 20. -P. 3987−3990.
- Sano S., Kuroda Y., Saito K., Ose Y., Nagao Y. Tandem reduction-olefination of triethyl 2-acyl-2-fluoro-2- phosphonoacetates and a synthetic approach to Cbz-Gly-VF (Z)-CF.C]-Gly dipeptide isostere // Tetrahedron. 2006. — V. 62, № 51. — P. 11 881−11 890.
- Sano S., Teranishi R., Nagao Y. Toward (Z)-selective Horner-Wadsworth-Emmons reaction of aldehydes with 2-fluoro-2-diethylphosphonoacetic acid // Tetrahedron Lett. -2002. -V. 43, № 50. P. 9183−9186.
- Patois C., Savignac P. Modification of the phosphorus substituents in a-chloromethylphosphonates as the key to (?)-selective syntheses of a-chlorinated acrylic esters // Synlett. -1991. № 7. — P. 517−519.
- McKenna C.E., Khawli L.A. Synthesis of halogenated phosphonoacetate esters I I J. Org. Chem. -1986. V. 51, № 26. — P. 5467−5471.
- TagoK., KogenH. A highly stereoselective synthesis of (E)-a-bromoacrylates // Tetrahedron. -2000. V. 56, № 45. — P. 8825−8831.1. ОЛ
- Still W.C., Gennari C. Direct synthesis of Z-unsaturated esters. A useful modification of the Horner-Emmons olefination // Tetrahedron Lett. 1983. — V. 24, № 41. — P. 4405−4408.
- Qing F.-L., Zhang X. A one-pot synthesis of (?)-a-bromo-a, p-unsaturated esters and their trifluoromethylation: a general and stereoselective route to (?)-a-trifluoromethyl-a, p-unsaturated esters I/ Tetrahedron Lett. 2001. — V. 42, № 34. — P. 5929−5931.
- Goumain S., JubaultP., FeassonC., CollignonN. Efficient electrosynthesis of a-chloro-a, P-unsaturated carboxylic and phosphonic esters using magnesium electrochemical activation // Synthesis. 1999. — № 6. — P. 981−984.
- Patrick T.B., Nadji S. Preparation of fluoroalkenes from fluoroacetonitrile // J. Fluorine Chem. 1990. — V. 49, № 1. — P. 147−150.
- Van Steenis J.H., van den Nieuwendijk A.M.C.H., van der Gen A. a-Fluoroacrylonitriles: Horner-Wittig synthesis and conversion into 2-fluoroallylamines and C-(l-fluorovinyl)nitrones II J. Fluorine Chem.- 2004. V. 125, № 1. — P. 107−117.
- Deng G.S., Liu C. Yu One-pot approach to the conversion of alcohols into a -halo-a, p-unsaturated esters // Chinese Chem. Lett. 2006. — V. 17, № 3. — P. 329−332.
- Chevrie D., Lequeux Т., Pommelet J.-C. Thia-Wittig-like reactions as a new route for the stereoselective synthesis of (Z)-fluoroalkenoates // Org. Lett. 1999. — V. 1, № 10. — P. 1539−1541.
- Zajc В., Kake S. Exceptionally mild, high-yield synthesis of a-fluoro acrylates // Org. Lett. -2006. V. 8, № 20. — P. 4457−4460.
- Wesolowski C.A., Burton D.J. Palladium-catalyzed stereospecific carboalkoxylation of 1,2-difluoro-l-iodoalkenes and a, P-difluoro-P-iodostyrenes // Tetrahedron Lett. 1999. -V. 40, № 12.-P. 2243−2246.
- LuL., Burton D, J. Palladium/copper (I) halide catalyzed stereospecific couplings of 1,2-difluorovinylstannanes with aryl iodides and vinyl halides // Tetrahedron Lett. 1997. — V. 38, № 44.-P. 7673−7676.
- Davis C.R., Burton D J. Stereoselective preparation of (Z)-a, p-difluorostyrenes and stereospecific conversion to (i?)-a, P-difuoro-(3-iodostyrenes // J. Org. Chem. 1997. — V. 62, № 26. -P. 9217−9222.
- Davis C.R., Burton D.J. Stereoselective preparation of (Z)-a, P-difluorostyrenes // Tetrahedron Lett. 1996. — V. 37, № 40. — P. 7237−7240.92
- Xue L., Lu L., Pedersen S.D., Liu Q., Narske R.M., Burton D.J. A novel stereospecific route to E and Z-2-substituted-l, 2-difluoroethenylstannanes // Tetrahedron Lett. 1996. -V. 37,№ 12.-P. 1921−1924.
- XueL., LuL., Pedersen S.D., LiuQ., Narske R.M., Burton D.J. A novel stereospecific route to (E) — and (Z)-(2-substituted-l, 2-difluoroethenyl)stannanes 11 J. Org. Chem. -1997. -V. 62, № 4.-P. 1064−1071.
- Fontana S.A., Davis C.R., He Y.-B., Burton D.J. The stereoselective preparation of с is and trans-1,2-difluoroethylene synthons // Tetrahedron. 1996. — V. 52, № 1. — P. 37−44.
- Yang Z.-Y., Burton D.J. A facile, general method for the preparation of fluorinated enynes // Tetrahedron Lett. 1990. — V. 31, № 10. — P. 1369−1372.
- Schoenberg A., Bartoletti I., Heck R.F. Palladium-catalyzed carboalkoxylation of aryl, benzyl, and vinylic halides II J. Org. Chem. 1974. -V. 39, № 23. — P. 3318−3326.
- LiJ.-H., Tang S. Palladium-catalyzed selective carbonylation of (?)-1,2-diidoalkenes // Synth. Commun. 2005. — V. 35, № 1. — P. 105−113.
- Li J-H., Li G., Jiang H.-F., Chen M.-C. A novel and efficient synthesis of maleic anhydrides by palladium-catalyzed dicarbonylation of terminal acetylenes in НгОЛНохапе // Tetrahedron Lett. 2001. — V. 42, № 39. — P. 6923−6924.
- Li J.-H., Jiang H.-F., Chen M.-C. Palladium-catalyzed dicarbonylation of terminal acetylenes: a new method for selective synthesis of unsaturated diesters and maleic anhydrides // Synth. Commun. 2001. — V. 31, № 20. — P. 3131−3134.
- WangY., Burton DJ. Copper (I)-only catalyzed reactions of (E)-2,3-difluoro-3-stannylacrylic ester with acid chlorides and mechanistic studies of the «Copper effect» in Stille coupling reactions // Org. Lett. 2006. — Y. 8, № 6. — P. 1109−1111.1ГП
- Gillet J.-P., Sauvetre R., Normant J.-F. Fluorovinylzinc reagents: access to fluorovinyl ketones, esters, and heterocycles //Synthesis. -1986. № 7. — P. 538−543.
- Zhang Q., LuL. A novel synthetic route to ethyl 3-substitoted-rram:-2,3-difluoro-2-acrylates and their reactions with nucleophiles // Tetrahedron Lett. 2000. — V. 41, № 44. -P. 8545−8548.
- Remion J., Dumont W., Krief A. New regiospecific routes to olefins from P-hydroxy selenides a stereospecific deoxygenation of epoxides — a C, C. connective route to olefins // Tetrahedron Lett. -1976. — V. 17, № 17. — P. 1385−1388.
- LabarD., Krief A. Connective (C-C) route to hindered epoxides and olefins from hindered ketones // J. Chem. Soc., Chem. Commun. -1982. P. 564−566.
- Yoshimatsu M., Murase Y., Itoh A., Tanabe G., Muraoka O. Z-selective or stereospecific alkenylation reaction: A novel synthetic method for a-fluoro-a, p-unsaturated esters // Chem. Lett. 2005. — V. 34, № 7. — P. 998−999.
- Hatanaka F., Tsuchiya M., Yoshimatsu M. The first synthesis and reaction of p-ethoxy-a-fluoro-a-(phenylselanyl)ethene: scandium or lanthanum triflate catalyzed a-fluoroformylalkenylation of aldehydes // Synlett. 2005. — № 14. — P. 2191−2194.
- KanaiM., Percy J.M. Short, stereoselective syntheses of a-fluoroalkenoate derivatives, a-fluoroenones and a-fluoroenals from HFC-134a // Tetrahedron Lett. 2000. — V. 41, № 14. — P.2453−2455.
- Concellon J.M., HuertaM., LlavonaR. Synthesis of (Z)-a-chloro-a, f3-unsaturated esters with complete stereoselectivity promoted by samarium diiodide // Tetrahedron Lett. 2004. — V. 45, № 24. — P. 4665−4667.
- NakatsuS., Gubaidullin A.T., MamedovV.A., Tsuboi S. A convenient synthesis of olefins via deacylation reaction // Tetrahedron. 2004. — V. 60, № 10. — P. 2337−2349.
- Рулев А.Ю. Геминально активированные галогенолефины в реакциях с N-нуклеофилами // Успехи химии. Т. 67, № 4. — С. 317−332.
- Gundermann K.D., HoltmannG. Atylenimin-carbonsaure-(2)-athylester. DL-Serin und DL-Isoserin aus a-Chlor-P-amino-propionsaure // Chem. Ber. 1958. — V. 91, № 1. — P. 160−167.
- Wessjohann L., McGafenG., DeMeijereA. 1,4-Addition of (diphenylmethylene)amine to acceptor substituted olefins. A versatile synthesis of protected p-amino acids, nitriles, and ketones //Synthesis. -1989.-№ 5. P. 359−363.
- Petit L., TouratierP. a, p-Unsaturated derivatives. II. Reaction of amines with bromo derivatives of a, P-unsaturated nitriles and reduction of a, p-diamino nitriles // Bull. Soc. Chim. Fr. -1968. -V. 3. P. 1136−1141.
- Kashima C., Tajima Т., Omote Y. The preparation and the nucleophilic reaction of 3,3-di (l-azolyl)-2-alken-l-ones, precursor of acetylketene derivatives // J. Heterocycl. Chem. -1984. -V. 21, № 1 P. 133−137.
- Jahnisch K., Seeboth H., Kraus E., Catasus N. P-Fur-yl-a-halogenacrylonitrile. II.
- Darstellung von p-Fur-2-yl-p (1,2,4-Triazolyl) Acrylonitrilen II J. Prakt. Chem. 1984. — V.326, № 4.-P. 676−678. 1
- Tronchet J.M.J., MartmO.R. Synthese et reactions de didesoxy-5,6-halogeno-6-a-D-xylo-hepteno-5-furannurononitriles. Communication preliminaire // Helv. Chim. Acta. -1977. V. 60, № 2. — P. 585−589.
- Jahnisch K., Seeboth H., Kraus E., Callejas D.R. P-Fur-2-yl-a-halogenacrylonitrile. I.
- Darstellung von P-Fur-2-yl-p-aminoacrylonitrilen und p-Fur-2-yl-a-aminoacrylonitrilen // J.
- Prakt. Chem. -1984. V. 326, № 4. — P. 556−560. 10ft
- Bouteville G., Gelas-Mialhe Y., Vessiere R. Synthese et stereochimie de quelques methoxycarbonyl-2- et cyano-2-aziridines // Bull. Soc. Chim. Fr. — 1971. V. 9. — P. 32 643 270.
- Burzin K., Enderer K. 2-Cyan-aziridin // Angew. Chem. 1972. — V. 84, № 3. — P. 108 109.11П
- Gundermann K.D., Burzin K., Sprenger F.J., SchulzeH. Verbesserte Synthese von 2-Cyan-aziridinen und Untersuchungen zu ihrer Isomerisierung // Chem. Ber. 1972. — V. 105, № 1.-P. 312−324.
- Lown J.W., Itoh Т., Ono N. Studies relating to aziridine antitumor antibiotics. Part I. Asymmetric syntheses. Part II. Chiral aziridines and their conversion to a-aminoacids // Can. J. Chem. -1973. V. 51. — P. 856−869.
- Rulev A.Yu., Maddaluno J., Pie G., Plaquevent J.C., Duhamel L. High pressure vs thermal activation of the conjugate addition of amines: a new access to spirocyclamines // J.Chem. Soc., Perkin Trans 1. 1998. — P. 1397−1401.
- Просяник JI.B., Марков В. И., Бондаренко C.B. Взаимодействие эфиров а, Р-дибромкарбоновых кислот с гидразинами // ЖОрХ. 1983. — Т. 19, № 12 — С. 24 802 484.
- Iriarte J., Camargo C., Crabbe P. Reaction of 6-bromobenzocyclohepten-5-one with amines. II J. Chem. Soc. Perkin Trans. 1. 1980. -V. 10. — P. 2077−2080.
- TarburtonP., Woller P.B., Badger R.C., Doomes E., Cromwell N.H. The role of solvent in conjugate additions leading to cis- and trans-1-alky 1−2-ary 1−3-carbo (aroyl)aziridines // J. Heterocycl. Chem. -1977. V. 14, № 3 — P. 459−464.
- TarburtonP., WolpaL. J, LoerchR.K., FolsomT.L., Cromwell N.H. The synthesis and spectra of new (?)-(trans) — and (Z)-(cis)-l-alkyl-2-aryl (alkyl)-3-aroylaziridines // J. Heterocycl. Chem. -1977. V. 14, № 7. — P. 1203−1207.
- Хомутов О.Г., ФиляковаВ.И., Пашкевич К. И. Синтез З-фторалкил-2-азиридинилкетонов // Изв. АН., Сер. хим. -1994. № 2. — С. 282−284.1 ЧЙ
- Хомутов О.Г., Пашкевич К. И. Взаимодействие полифторалкилсодержащих азиридинилкетонов с галогеноводородами // Изв. АН., Сер. хим. 1996. — № 3. — С. 684−686.
- Barros М.Т., Maycock C.D., Ventura M.R. A synthesis of aziridines from a-iodoenones // Tetrahedron Lett. 2002. — V. 43, № 24. — P. 4329−4331.
- Has-Becker S., Bodmann K., Kreuder R., Santoni G., Rein Т., Reiser O. High-pressure induced Domino-Horner-Wadsworth-Emmons (HWE) Michael Reactions // Synlett. -2001.-№ 9.-P. 1395−1398.
- Boucher J.-L., Stella L. Dienophilie des olefins captodative: influence de Tencombrement sterique des a-alkylthioacrylonitriles sur la stereoselectivite des reactions de Diels-Alder // Bull. Soc. Chim. Fr. 1986. — № 2. — P 276−282.
- Gundermann K.-D., Thomas R. Uber Mercapto-acrylsaure-Derivate, II. Mitteil.: Zum Bildungsmechanismus der a-Alkylmercapto-acrylnitrile // Chem. Ber. -1956. V. 89, № 5. -P. 1263−1270.
- Gundermann K.-D. Uber Mercapto-acrylsaure-Derivate, I. Mitteil.: a-Benzylmercapto-aciylnitril und sein Dimeres // Chem. Ber. -1955. Y. 88, № 9. — P. 1432−1436.
- Auwers V., Huegel R. Uber gechlorte Zimtaldoxime und Zimtsaurenitrile // J. Prakt. Chem. -1935. V. 143, № 7−9. — P. 179−188.
- Maligres P.E., Krska S.W., Humphrey G.R. Enantioselective hydrogenation of a-aryloxy a, P-unsaturated acids. Asymmetric synthesis of a-aryloxycarboxylic acids // Org. Lett. — 2004.-V. 6, № 18.-P. 3147−3150.
- Bradley P.J., Grayson D.H. The Diels-Alder reactivity of (?)-3-phenylsulfonylprop-2-enenitrile, a cyanoacetylene equivalent II J. Chem. Soc., Perkin Trans. 1. 2002. — V. 15. -P.1794−1799.
- Мовсум-заде Э.М., Мамедов М. Г., Шахиев И. А. Синтез и превращения алкоксинитрилов 11 ЖОрХ. 1976. — Т. 12, вып. 8 — С. 1687−1689.
- Concellon J.M., Huerta М. Highly selective reaction of a-halo-a, p-unsaturated esters with ketones or aldehydes promoted by Sml2: An efficient alternative access to Baylis-Hillman adducts И J. Org. Chem. 2005. — V. 70, № 12. — P. 4714−4719.
- Itoh K., Kishimoto S. The reaction of 3-nitrostyrenes with 2-mcthoxyfuran: a novel formation of isoxazoline N-oxide together with Michael adducts // New J. Chem. 2000. -V. 24.-P. 347−349.
- Mironiuk-Puchalska E., Kolaczkowska E., Sas W. Synthesis of (±)-branched-chain azaisonucleosides via Michael addition of 5-nitro-2,2-pentamethylene-l, 3-dioxane to methyl 2-bromoacrylate // Tetrahedron Lett. 2002. — V. 43, № 46. — P. 8351−8354.
- Dauzonne D., Demerseman P. A convenient synthesis of 3-chloro-3,4-dihydro-4-hydroxy-3-nitro-2-phenyl-2H-l-benzopyrans // Synthesis. 1990. — № 1. — P. 66−70.
- Гиллер C.A., Еремеев A.B., Кальвиньш И .Я., Лиепинып Э. Э., Тихомиров Д. А. Реакции а-хлоракрилонитрила с гидразинами И ХГС. 1975. -№ 2. — С. 246−249.
- Jahnisch К., Seeboth Н., Kuban R.J. p-Fur-2-yl-a-halogenacrylonitrile. VII. Reaktionen von P-(5-Brom-fur-2-yl)-a-bromacrylonitril mit Mercaptan, Thioharnstoff und Thioharnstoffderivaten // J. Prakt. Chem. 1987. — V. 329, № 1. — P. 113−118.
- Marsura A., Luu Due C. A new method for the synthesis of 2,6-disubstituted 4(3//)-pyrimidinones from benzamidine // Synthesis. 1982. — № 7. — P. 595.
- Marsura A., Luu Due C., Gellon G. New one-step synthesis of functionalized 2-imidazolines // Synthesis. 1985. — № 5. — P. 537.
- Липсон В.В., Орлов В. Д., Десенко С. М., Шишкина С. В., Шишкин О. В., Широбокова М. Г. 1,2,3,4-тетрагидропиримидо1,2-а.бензимидазол-2- и 4-оны I/ XFC. -2000.-№ 9.-С. 1190−1196.
- Липсон В.В., Десенко С. М., Орлов В. Д., Шишкин О. В., Широбокова М. Г., Черненко В. Н., Зиновьева Л. И. Циклоконденсация 3-амино-1,2,4-триазолов с эфирами замещённых коричных кислот и ароматическими непредельными кетонами // ХГС. -2000. -№ 11. С. 1542−1549.
- Bills С., GeburaS., MeekJ., Sweeting О. New synthesis of uric acid and 1,7-dimethyluric acid // J. Am. Chem. Soc.- 1962. V. 27, № 12. — P. 4633−4635.
- Noetzel M.W., Rauch K., Labahn Т., de Meijere A. Domino reactions of amidines with methyl 2-chloro-2-cyclopropylidenacetate as an efficient access to cyclobutene-annelated pyrimidinones // Org. Lett. 2002. — V. 4, № 5. — p. 839−841.
- О’Neil I. A., Cleator E., Southern J.M., BickleyJ.F., Tapolczay D.J. The stereospecific addition of hydroxylamines to a, P-unsaturated sulfones, nitriles and nitro compounds // Tetrahedron Lett. 2001. — V. 42, № 46. — P. 8251−8254.
- Grison C., Geneve S., Coutrot P. Enantioselective synthesis of a, P-unsaturated y- and 5-lactams // Tetrahedron Lett. 2001. — V. 42, № 23. — P. 3831−3834.
- Tronchet J.M.J., Martin O., Grouiller A., Sarda N. C-nucleosides aminoisoxazoliques. Communication preliminaire // Helv. Chim. Acta. -1979. V. 62, № 3. — P. 833−837.
- Jahnisch K., Seeboth H., Catasus N. P-Fur-2-yl-a-halogen-acrylonitrile Darstellung von 3-Amino-5-fur-2-yl-isoxazolen // Z. Chem. -1984. — V. 24. — P. 93−94.
- BartschH., SchwarzO. Synthesis of 3,4-dihydro-2H-l, 4-benzoxazin-2- and 3-carbonitriles. 11. Chemistry of 1,4-oxazine // J. Heterocycl. Chem. 1983. — V. 20, № 1 -P. 45−48.
- БуевичВЛ., Рудченко B.B., Гринева B.C., Перекалин В. В. Синтез производных бензоксазола с нитрогруппой в боковой цепи // ЖОрХ. 1978. — Т. 14, № 10 — С. 21 972 201.
- НечайН.И., ПоткинВ.И., КабердинР.В. Реакции 1,3-динитротетрахлор-1,3-бутадиена с некоторыми нуклеофильными реагентами // ЖОрХ. 2000. — Т. 36, № 5 -С. 676−682.
- Wessjohann L., De Meijere A. Tailoring the reactivity of small ring building blocks for organic synthesis // Synlett. 1990. — V. 1. — P. 20−32.
- EidemA., UndheimK., ReistadK.R. N-Quaternary compounds. XVII. Addition of thioamides to a-bromo-a, p-unsaturated acids. // Acta Chem. Scand. 1971. — V. 25, № 1, -P. 1−4.17П
- UndheimK., LieR. N-Quaternary compounds. XXXII. Michael addition of 2(1H)-pyridinethiones to a -bromo-a, P-unsaturated acids. И Acta Chem. Scand. -1973. V. 27, № 5.-P. 1749−1755.1п1
- Osborne N.F. The chemistry of 4-mercaptoazetidin-2-ones. Part 2. Synthesis ofbisnorpenicillins II J. Chem. Soc., Perkin Trans. 1. -1980. P. 150−155.111
- Osborne N.F. The chemistry of 4-mercaptoazetidin-2-ones. Part 1. Preparation and properties of (3i?, 47?)-4-mercapto-3-phenoxyacetamidoazetidin-2-one // J. Chem. Soc., Perkin Trans. 1. 1980. — P. 146−149.1.x
- Dauzonne D., JosienH., Demerseman P. A general synthesis of l-nitro-2-phenyl-4-oxospiro2.5.octanes // Synthesis. -1992. № 3. — P. 309−314.
- Dauzonne D., Adam-Launay A. A convenient procedure for the preparation of 5,6-dihydro-6-nitro-5-phenylfuro2,3-d.pyrimidin-4(3i/)-ones and 5-phenylfiiro[2,3-d]pyrimidin-4(3#>ones // Tetrahedron. -1992. V. 48, № 15. — P. 3069−3080.
- Hagiwara H., SatoK., Suzuki Т., AndoM. Tandem nucleophilic reaction of 1,3-dicarbonyl compounds to methyl a-bromoacrylate: 3+2.heteroannulation leading to hydroforan derivatives // Tetrahedron Lett. -1997. V. 38, № 12. — P. 2103−2106.
- Arai S., Nakayama K., Suzuki Y., Hatano K., Shioiri T. Stereoselective synthesis of dihydrofurans under phase-transfer catalyzed conditions // Tetrahedron Lett. 1998. — V. 39, № 52.-P. 9739−9742.
- Huddleston P.R., Barker J.M., Adamczewska Y.Z., WoodM.L., Holmes D. Synthesis and chemistry of some thieno3,2-d.-l, 2,3-triazin-4(3H)-ones. // J. Chem. Res. Synopses. -1993.-V. 2.-P. 72−73.
- Chang М-Y., SunP-P., Chen S-T., Chang N-C. A facile synthesis of 3-aryl pyroglutamic acid. Facile synthesis of baclofen and chlorpheg // Tetrahedron Lett. 2003. — V. 44, № 28. -P. 5271−5273.
- Sun P.P., Chang M.-Y., Chiang M.Y., Chang N.-C. A facile route to polysubstituted N-benzyl pyroglutamates // Org. Lett. 2003. — V. 5, № 10. — P. 1761−1763.
- ShirahaseM., KanemasaS., Oderaotoshi Y. Chiral DBFOX/Ph complex catalyzed enantioselective nitrone cycloadditions to a,|3-unsalurated aldehydes // Org. Lett. 2004. -V. 6, № 5.-P. 675−678.
- Katritzky A.R., Qiu G., Yang В., He H.Y. Novel syntheses of indolizines and pyrrolo2, l-a.isoquinolines via benzotriazole methodology // J. Org. Chem. 1999. — V. 64, № 20.-P. 7618−7621.
- Arrault A., Guillaumet G., Leger J.-M., Jarry C., Merour J.-Y. A straightforward synthesis of oxazino2,3,4-z}'.quinoline derivatives from 8-hydroxyquinolines // Synthesis. -2002.-№ 13.-P. 1879−1884.1 oc
- Greengrass C.W., Hoople D.W.T., Nobbs M.S. Studies on 1-carbadethiacephems, part III: synthesis of 2,3-difunctionalised 1-carbadethiacephem derivatives // Tetrahedron Lett. -1982. V. 23, № 23. — P. 2419−2422.
- BajjiA.C., Nanya S., ButsuganY. Synthesis of indeno2, l-b. l, 4]benzothiazine derivatives from 2-bromoinden-l-ones. // J. Heterocycl. Chem. 1993. — V. 30, № 2.- P. 361−363.
- Nanya S., Ishida H., Moiji E.J., Butsugan Y. Condensations of brominated products of o-acetylbenzophenone with several primary amines. II J. Heterocycl. Chem. 1994. — V. 31, № 2.-P. 401−403.
- Nozoe Т., Shindo K., Wakabayashi H., Ishikawa S. Polyannulated tropylium compounds having benzothiazine and related heterocyclic rings. Formation of o- and p-benzoquinonoid products by rearrangement. // Heterocycles. -1989. V. 29, № 8. — P. 1459−1464.
- Nitta M., Mori S., lino Y. The reaction of (vinylimino)phosphoranes and related compounds. 18. A novel route to 1-azaazulenes by the reaction of a -amino enones with activated tropones. // Heterocycles. -1991. V. 32, № 1. — P. 23−28.
- Baldwin J.E., OtsukaM., Wallace P.M. Synthetic studies on tabtoxin. Synthesis of a naturally occuring inhibitor of glutamine synthetase, tabtoxin ine- p-1 actam, and analogues 11 Tetrahedron. 1986. — V. 42, № 12. — P. 3097−3110.
- VieiraE., VogelP. Copper (I) — and copper (II)-catalyzed Diels-Alder additions of a-substituted acrylonitrile to fiiran. The synthesis of 7-oxa-bicyclo2.2.1.hept-5-en-2-one // Helv. Chim. Acta. 1982. -V. 65, № 6. — P. 1700−1706.
- Damiano-Gal J. Geribaldi S, Torri G, Rouillard M, Azzaro M. Synthese dans la serie bicyclio2,2,2.octanique: III synthese d’a-cjloronitrines, de cetones et de y-dicetones bicycliques I I Bull. Soc. Chim. Fr. -1977. № 3−4. — P. 345−350.
- SchudaP.F., Bennett J.M. The Diels-Alder reactions of furans 1: the reactions of furans with a-chloroacryonitrile // Tetrahedron Lett. 1982. — V. 23, № 52. — P. 5525−5528.
- Копраненков B.H., Гончарова JI.C., ЛукьянецЕ.А. Синтез 7,8-дициано2,3:5,6-дибензо.бицикло[2,2,2]окта-2,5,7-триена И ЖОХ. -1988. Т. 58,№ 5. — С. 1186−1187.
- Selvakumar N., Subba Rao G.S.R. A new total synthesis of (±)-norprezizanone // Tetrahedron Lett. -1993. V. 34, № 48. — P. 7789−7792.
- Ohkita M., Nishizawa O., Tsuji Т., Nishida S. Single step synthesis of norbornan-2-one dithioacetals from cyclopent-2-en-l-one dithioacetals and dienophiles // J. Chem. Soc., Chem. Commun. -1993. V. 22. — P. 1676−1677.
- ShimS.C., ParkS.K. Photocycloaddition reaction of 1,4,5,8-tetraazaphenantrene with some olefins //Chem.Lett. 1986. — Y. 15, № 1.- P. 23−26.
- BienfaitB., Coppe-Motte G., MerenyiR., VieheH.G., Sicking W., SustmannR. p-Cyanocyclobutenone as a highly reactive dienophile in comparison to P-cyanocyclopentenone // Tetrahedron. 1991. — V. 47, № 38. — P. 8167−8176.
- Ficini J., Touzin A.M., Krief A. Attempts at synthesis of cyclobutadienes II Bull. Soc. Chim. Fr.-1972.-P. 2388.
- Cobb R.L., Mahan J.E. Chemistry of cyclobutene-l, 2-dicarbonitrile. 2. Cycloadducts // J. Org. Chem. 1977. — V. 42, № 15. — P. 2597−2601.
- TeoY.-C., LohT.-P. Catalytic enantioselective Diels-Alder reaction via a chiral indium (III) complex // Org. Lett. 2005. — V. 7, № 13. — P. 2539−2541.
- Fu F., Teo Y.-C., Loh T.-P. Catalytic enantioselective Diels-Alder reaction in ionic liquid via a recyclable chiral In (III) complex // Org. Lett. 2006. — V. 8, № 26. — P. 59 996 001.
- GagnierS.V., LarockR.C. Palladium-catalyzed heteroannulation of 1,3-dienes to form a-alkylidene-y-butyrolactones И J. Org. Chem. 2000. -V. 65, № 5. — P. 1525−1529.
- Corey E.J., Shibata Т., Lee T.W. Asymmetric Diels-Alder reactions catalyzed by a triflic acid activated chiral oxazaborolidine // J. Am. Chem. Soc. 2002. — V. 124, № 15. — P. 3808−3809.
- ThormeierS., CarboniB., KaufmannD.E. Chiral boronates versatile reagents in asymmetric synthesis // J. Organomet. Chem. — 2002. — V. 657, № 1. — P. 136−145.
- Faller J.W., Grimmond B.J., D’Alliessi D, G. An application of electronic asymmetry to highly enantioselective catalytic Diels-Alder reactions // J. Am. Chem. Soc. 2001. — V. 123, № 11.-P. 2525−2529.
- Капо Т., Konishi Т., Konishi S., Maruoka K. Design of chiral tin (IV) aryloxide as a mild Lewis acid catalyst for enantioselective Diels-Alder reaction // Tetrahedron Lett. 2006. -V. 47,№ 6.-P. 873−875.
- Kraus G.A., Kim J. Tandem Diels-Alder/Ene reactions // Org. Lett. 2004. — V. 6, № 18. -P. 3115−3117.
- Wang Y., Burton D.J. A facile, general synthesis of 3,4-difluoro-6-substituted-2-pyrones И J. Org. Chem. 2006. — V. 71, № 10. — P. 3859−3862.
- Xi С., Chen С., Lin J., Hong X. Pd-catalyzed one-pot multicomponent coupling reaction for the highly regioselective synthesis of polysubstituted benzenes // Org. Lett. 2005. — V. 7, № 2. — P. 347−349.
- Dai W.-M., Wu A. First synthesis of a highly strained cyclodeca-l, 5-diyne skeleton via intramolecular Sonogashira cross-coupling // Tetrahedron Lett. 2001. — V. 42, № 1. — P. 81−83.
- Dai W.-M., Wu A., Hamaguchi W. Intramolecular Nozaki-Hiyama-Kishi reactions and Ln (III)-catalyzed allylic rearrangement as the key steps towards 10-membered ring enediynes // Tetrahedron Lett. 2001. — V. 42, № 25. — P. 4211−4214.
- Zhang X., Qing F.-L., Peng Y. The stereospecific trifluoromethylation of a-iodo-a, p-unsaturated esters: a novel synthesis of (Z)-a-trifluoromethyl-a, 3-unsaturated esters // J. Fluorine Chem. 2001. — V.108, № 1. — P. 79−82.910
- Thibonnet J., Knochel P. Preparation of functionalized alkenylmagnesium bromides via a bromine-magnesium exchange // Tetrahedron Lett. 2000. — V. 41, № 18. — P. 3319−3322.
- Jalil A.A., Kurono N., Tokuda M. Facile synthesis of 2-arylpropenoic acid esters by cross-coupling using electrogenerated highly reactive zinc and a palladium catalyst // Synlett. 2001. — № 12. — P. 1944−1946.
- Jalil A.A., Kurono N., Tokuda M. Synthesis of the precursor of anti-Inflammatory agents by cross-coupling using electrogenerated highly reactive zinc // Synthesis. 2002. — № 18. -P. 2681−2686.
- Jalil A.A., Kurono N., Tokuda M. Facile synthesis of ethyl 2-arylpropenoates by cross-coupling reaction using electrogenerated highly reactive zinc // Tetrahedron. 2002. — V. 58, № 37.-P. 7477−7484.
- ShastinA.V., Korotchenko V.N., Nenajdenko V.G., BalenkovaE.S. A novel synthetic approach to dichlorostyrenes // Tetrahedron. 2000. — V. 56, № 35. — P. 6557−6563.
- Korotchenko N.V., ShastinA.V., Nenajdenko V.G., Balenkova E.S. Olefmation of aromatic ketones: synthesis of mono- and dihaloalkenes // J. Chem. Soc., Perkin Trans 1. -2002.-V. 7.-P. 883−887.
- ShastinA.V., Korotchenko V.N., Nenajdenko V.G., Balenkova E.S. A novel synthesis of |3,p-dibromostyrenes // Synthesis. 2001. — № 14. — P. 2081−2084.
- Korotchenko V.N., ShastinA.V., Nenajdenko V.G., Balenkova E.S. Novel efficient synthesis of dibromoalkenes. A first example of catalytic olefination of aliphatic carbonyl compounds // Org. Biomol. Chem. 2003. — V. 1. — P. 1906−1908.
- Ненайденко В.Г., ШастинА.В., Коротченко B.H., Баленкова Е. С. Превращение ароматических альдегидов в дихлоралкены // Изв. АН, Сер. хим. -2001. Т. 50, № 6. -С. 1003−1006.
- ШастинА.В., Коротченко В. Н., Ненайденко В. Г., Баленкова Е. С. Новый метод синтеза Р-бромстиролов // Изв. АН, Сер. хим. 2001. — Т. 50. — С. 1334−1337.
- ШастинА.В., Коротченко В. Н., ВарсеевГ.Н., Ненайденко В. Г., Баленкова Е. С. Новый метод синтеза 2-иодстиролов II ЖОрХ. 2003. — Т. 39. — С. 433−436.
- Korotchenko V.N., Shastin A.V., Nenajdenko V.G., Balenkova E.S. A novel approach to fluoro-containing alkenes // Tetrahedron. 2001. — V. 57, № 35. — P. 7519−7527.
- Nenajdenko V.G., Varseev G.N., Korotchenko V.N., Shastin A.V., Balenkova E.S. A novel direct synthesis of (2,2-difluorovinyl)benzenes from aromatic aldehydes II J. Fluorine Chem.- 2003. V. 124, № 1. — P. 115−118.
- Nenajdenko V.G., Shastin A.V., Korotchenko V.N., Varseev G.N., Balenkova E.S. A novel approach to 2-chloro-2-fluorostyrenes // Eur. J. Org. Chem. 2003. — № 2. — P. 302 308.
- Nenajdenko V.G., Varseev G.N., Shastin A.V., Balenkova E.S. The catalytic olefination reaction of aldehydes and ketones with CBr3CF3 И J. Fluorine Chem. 2005. — V. 126, № 6.-P. 907−913.
- Коротченко B.H., ШастинА.В., Ненайденко В. Г., Баленкова Е. С. Каталитическое олефинирование карбонильных соединений. Влияние структуры карбонильного соединения на направление реакции // Изв. АН, Сер. хим. 2003. — Т. 52. — С. 469−474.
- Коротченко В.Н., ШастинА.В., Ненайденко В. Г., Баленкова Е. С. Реакция каталитического олефинирования гидразонов полигалогеналканами. Исследование хемоселективности образования алкенов НЖОрХ. 2003. — Т. 39. — С. 562−567.
- Ненайденко В.Г., Коротченко В. Н., ШастинА.В., Тюрин Д. А., Баленкова Е. С. Реакция каталитического олефинирования карбонильных соединений. Исследование стереоселективности образования алкенов // Изв. АН, Сер. хим. 2003. — Т. 52. — С. 1740−1745.
- Dakin L.A., Schaus S.E., Jacobsen E.N., Panek J.S. Carbenoid insertions into the silicon-hydrogen bond catalyzed by chiral copper (I) schiff base complexes // Tetrahedron Lett. -1998. V. 39, № 49. — P. 8947−8950.
- Gettwert V., Krebs F., Maas G. Intramolecular copper- and rhodium-mediated carbenoid reactions of a-(propargyloxy)silyl-a-diazoacetates // Eur. J. Org. Chem. 1999. — № 5. — P. 1213−1221.
- Aggarwal V.K., Ford J.G., Jones R.V., Fieldhouse R.H. Camphor derived 1,4-oxathianes for carbonyl epoxidation // Tetrahedron: Asymmetry. -1998. V. 9, № 10. — P. 1801−1807.
- Chari R.V.J., Wemple J. A simple, efficient synthesis of p-methylene phenylalanine. A new approach to the preparation of p, y-unsaturated a-amino acid enzyme substrate analogs // Tetrahedron Lett -1979. V. 20, № 2. — P. 111−114.
- NakamuraL, HaradaK. Sterically controlled synthesis of c/s-l-benzyl-2-methoxycarbonyl-3-phenylaziridine II Heterocycles. 1978. — V. 9, № 4. — P. 473−480.
- Makosza M., Podraza R., Bialecki M. New simple method of synthesis of substituted halo alkenes via knoevenagel-type condensation of aldehydes with a-halo-substituted CH-acids // Gazz. Chim. Ital. 1995. — V. 125, № 12. — P. 601−603.
- MiuraM., OkuroK., HattoriA., Nomura M. Carbonylation of vinyl halides with carbonylcobalt // J. Chem. Soc., Perkin Trans. 1. 1989. — V. 1. — P. 73−76.
- Son J.S., Jung K.S., Kim H.R., Kim J.N. The reactions of a, p-unsaturated esters by HCl/DMF/Oxone system // Synth. Commun. 1998. — V. 28, № 10. — P. 1847−1855.
- Kruper W.J.Jr., Emmons A.H. Synthesis of a-halocinnamate esters via solvolytic rearrangement of trichloroallyl alcohols II J. Org. Chem. 1991. — V. 56, № 10. — P. 33 233 329.
- Мамедов В.А., Нуретдинов И. А., Полушина B.JI. Взаимодействие N, N-диметиламида и метилового эфира З-фенил-З-хлор-2-кетопропионовой кислоты с трифенилфосфином И Изв. АН СССР, Сер. хим. 1989. — Т. 6. — С. 1395−1396.
- Hansen Р.Е. Carbon-hydrogen spin-spin coupling constants // Prog. Nucl. Magn. Reson. Sped. -1981. V. 14. — P. 175−296.
- Cornia A., Folli U., Sbardellati S., Taddei F. Electron transfer in the reactions of organic trichloromethyl derivatives with iron (II) chloride // J. Chem. Soc., Perkin Trans. 2. 1993. -V. 10.-P. 1847−1853.
- Moore H.W., Mercer F., KunertD., AlbaughP. Cyanoketenes. Cycloadditions of halocyanoketenes to benzaldehydes // J. Am. Chem. Soc. 1979. — V. 101, № 18. — P. 54 355 436.
- ГордонА., Форд P. Спутник химика. M: Мир, 1976. — 177 с. Gordon A.J., FordR.A. The chemists companion. A handbook of practical data, techniques and references. — New York: Wiley — Interscience, 1972. — 177 p.
- Bolli M.H., Ley S.V. Development of a polymer bound Wittig reaction and use in multi-step organic synthesis for the overall conversion of alcohols to (3-hydroxyamines // J. Chem. Soc., Perkin Trans. 1. -1998. V. 15. — P. 2243−2246.
- Fairhurst J., Horwell D.C., Timms G.H. A synthesis of cis-a-unsaturated nitriles by kinetically controlled decarboxylation // Tetrahedron Lett. 1975. — V. 16, № 44. — P. 38 433 844.
- AtsutaH., FujiwaraK., MuraiA. Diastereoselective synthesis of the GH ring part of ciguatoxin // Synlett. -1997. № 3. — P. 307−309.
- Markl G. Triphenylphosphin-halogen-acyl-methylene // Chem. Ber. 1962. — B. 95. — S. 3003−3007.
- Kowalski C.J., Weber A.E., Fields K.W. a-Keto dianion precursors via conjugate additions to cyclic a-bromoenones II J. Org. Chem. 1982. — V. 47. — P. 5088−5093.
- Bowman W., Bridge C., Cloonan M., Leach D. Synthesis of heteroarenes via radical cyclisation onto nitriles // Synlett. 2001. — № 6. — P. 765−768.260
- Saraf S.D. Reaction of thionyl bromide with aromatic aldehydes I I J. Prakt. Chem.1981. V. 323, № 4. — P. 673−676.
- Masure D., Chuit C., Sauvetre R., Normant J.F. Addition of organometallic compoundsto 2-chloro-l, l-difluoro-3-hydroxy-l-alkenes. A new synthesis of a,(3-unsaturated a-chloroaldehydes and ketones // Synthesis. -1978. № 6. — P. 458−460. 262
- Meldrum A.N., Vad G.M. Condensation of chloral and bromal with polyhydric alcohols II J. Indian Chem. Soc. -1936. Y. 13. — P. 118−122.
- Рулев А.Ю., Моков A.C., Кривдин Л. Б., Кейко И. А., Воронков М. Г. Спектры ЯМР 'Н и 13С 2-галоген-2-алкеналей и их ацеталей ИЖОрХ. 1995. — Т. 31. — С. 1634−1638.
- Коротченко В.Н., Ненайденко В. Г., Баленкова Е. С., Шастин А. В. Олефинирование карбонильных соединений, новейшие и классические методы // Успехи химии. 2004. -Т. 73, № 10.-С. 1039−1074:я//
- Huang Y.R., Katzenellenbogen J.A. Regioselective synthesis of l, 3,5-triaryl-4-alkylpyrazoles: novel ligands for the estrogen receptor // Org. Lett. 2000. — V. 2, № 18. -P. 2833−2836.
- Dang Q., Brown B.S., Erion M.D. 5-Aminopyrazoles as dienophiles in the inverse electron demand Diels-Alder reactions of 2,4,6-tris(ethoxy-carbonyl)-l, 3,5-triazine: Syntheses of pyrazolopyrimidines // J. Org. Chem. 1996. — V. 61, № 16. — P. 5204−5205.
- Katritzky A.R., WangM., Zhang S., VoronkovM.V. Regioselective synthesis of polysubstituted pyrazoles and isoxazoles // J. Org. Chem. 2001. — V. 66, № 20. — P. 67 876 791.
- Cusmano S., Sprio V. The behavior of «ylidenic» bonds toward some reagents. VI. The structure of compounds formed by the action of hydrazine hydrochloride on benzylidene derivatives of 0-oxo nitriles // Gazz. Chim. Ital. -1982. V. 82. — P. 420−428.
- Fomum Z.T., Landor S.R., Landor F.D., Mpango G.W.P. Allenes. Part 39. The synthesis of 3-alkyl-5-aminopyrazoles and ЗЯ-indoles from allenic or acetylenic nitriles // J. Chem. Soc., Perkin Trans. 1. 1981. — P. 2997−3001.
- Hartmann H., Liebscher J. A facile synthesis of 5-aminopyrazoles by the reaction of |3-chlorocinnamonitriles with hydrazine hydrate // Synthesis. — 1984. № 3. — P. 276−277.
- Searles S., KashH.M. The structure of the so-called «6-phenyl-1,4-dihydro-6W-triazine» II J. Org. Chem. 1954. — V. 19, № 6. — P. 928−929.
- Meyer E., BergeP., OehlerR., SchletterE. CVI. Neue Beitrage zur Kenntnis der dimolekularen Nitrile II J. Prakt. Chem. -1914. V. 90, № 1. — P. 1−52.
- EgeG., Arnold P. C-Unsubstituierte 1-Alky 1−3-aminopyrazole aus 2-Chloroacrylnitril bzw. 2,3-Dichloropropannitril und Alkylhydrazinen // Synthesis. —1976. № 1. — P. 52.
- Lautens M., Roy A. Synthetic studies of the formation of oxazoles and isoxazoles from N-acetoacelyl derivatives: scope and limitations // Org. Lett. 2000. — V. 2, № 4. — P. 555 557.
- Takase A., Murabayashi A., Sumimoto S., Ueda S., Makisumi Y. Practical synthesis of 3-amino-5-tert-butylisoxazole from 4,4-dimethyl-3-oxopentanenitrile with hydroxylamine. ИHeterocycles-1991. V. 32, № 6. — P. 1153−1158.
- Dines M., Sheinbaum M.L. A two-step synthesis of 5-aminoisoxazoles from olefins // Tetrahedron Lett. 1969. — V. 10, № 54. — P. 4817−4819.
- Dadd M.R., Claridge T.D.W., PettmanA.J., Knowles С.J. Biotransformation of benzonitrile to benzohydroxamic acid by Rhodococcus rhodochrous in the presence of hydroxylamine // Biotechnology Lett. 2001. — V. 23. — P. 221−225.1. ЛОС
- BeijerF.H., KooijimanH., Spek A.L., Sijbesma R.P., MeijerE.W. Self-complementarity achieved through quadruple hydrogen bonding // Angew. Chem., Int. Ed. 1998. — V. 37, № 1−2.-P. 75−78.
- Japan pat. 1 174 967 /1. Iwai, N. Nakamura and K. Schnozaki // Chem. Abstrs. 1968. -V. 68.-P. 69035m.
- BreukerJ., Van der PlasH.C. The Chichibabin amination of 4-phenyl- and 4-tert-butylpyrimidine Reel.: J. R. Neth. Chem. Soc. -1983. V. 102, № 7−8. — P. 367−372.
- Cooke G., De Cremiers H.A., Rotello V.M., Tarbit В., Vanderstraeten P.E. Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions // Tetrahedron. 2001. — V. 57, № 14. — P. 2787−2789.
- Migianu E., Kirsh G. Synthesis of new thienoZ>.azepinediones from a-methylene ketones // Synthesis. 2002. — № 8. — P. 1096−1100.
- HartmannH., Liebscher J. A simple method for the synthesis of 5-aryl-3-amino-2-alkoxycarbonylthiophenes // Synthesis. -1984. № 3. — P. 275.
- Le Menn J.-C., Sarrazin J., Tallec A. Carbanions phosphonate prepares par voie electrochimique: formation et reaetivite vis-a-vis d’un aldehyde // Can. J. Chem. 1989. -V. 67.-P. 1332−1343.
- Olpp Т., Brueckner R. Stereoselective preparation of (?)-a-bromoacrylates from mixtures of brominated ando phosphonates // Synthesis. 2004. — № 13. — P. 2135 — 2152.
- Tay M.K., About-Jaudet E., CollignonN., TeuladeM.P., SavignacP. a-Lithioalkylphosphonates as functional group carriers, an in situ acrylic ester synthesis // Synth. Commun. 1988. — V. 18, № 12. — P. 1349−1362.
- Solladie-Cavallo A., Lupattelli P., Bonini C., De Bonis M. anti-Ethyl p-thienyl-p-amino-a-hydroxy propionate: a regio and stereoselective ring opening of trans-ohy 2-thienyl-glycidate // Tetrahedron Lett. 2003. — V. 44, № 27. — P. 5075 — 5078.
- Newkome G.R., Fishel D.L. Synthesis of simple hydrazones of carbonyl compounds by an exchange reaction II J. Org. Chem. 1966. — V. 31, № 3. — P. 677−681.
- Iiarnsberger H.F., Cochran E.L., Szmant H.H. The basicity of hydrazones // J. Am. Chem. Soc. 1955. — V. 77, № 19. — P. 5048−5050.
- Pearson D.E., Carter K.N., Greer C.M. The rearrangement of hydrazones and semicarbazones // J. Am. Chem. Soc. -1953. V. 75, № 23. — P. 5905−5908.
- Loupy A., Sogadji K., Seyden-Penne J. A stereoselective synthesis of trans-2-alkenenitriles I/ Synthesis. -1977. № 2. — P. 126−127.
- Texier-Boullet F., FoucaudA. The Wittig-Horner reaction in solid-liquid two phase systems // Synthesis. -1979. № 11. — P. 884.
- Merritt A.B., Chun S., Jiuqing Z. Palladium-imidazolium carbene catalyzed Mizoroki-Heck coupling with aryl diazonium ions // Org. Lett. 2002. — V. 4, № 12. — P. 2079−2082.
- Руководство по неорганическому синтезу. В 6 томах / под ред. БрауэраГ.Т. М.: Мир, 1985.-Т. 4.-С. 1063. а
- Claisse J.A., FoxtonM. W, Gregory G.I., SheppardA.H., TileyE.P., Warburton W.K., Wilson M.J. Some 5-unsubstituted acetylenic and vinylic 1,2,4-oxadiazoles И J. Chem. Soc., Perkin Trans. 1. 1973. — P. 2241−2249.
- Chase W., Walker J. The preparation of enol ethers from certain p-keto-nitriles // J. Chem. Soc. 1953. — P. 3518−3525.