Reactions of 3-alkylsulfanyl-2-arylazo-3-(1-azacycloalk-1-yl)acrylonitriles with maleimide / Belskaya N.P., Koksharov A.V., Deryabina T.G., Eltsov O.S., Slepukhin P.A., Bakulev V.A. // Russian Chemical Bulletin. - 2010. - V. 59, l. 4. - P. 833-837.

ISSN:

10665285

Type:

Article

Abstract:

Reactions of 2-arylazo-3-(1-azacycloalk-1-yl)-3- methylsulfanylacrylonitriles with male-imide in benzene gave octahydropyrrolo[3,4-a]pyrrolizines 2a-c, decahydro-2,7a-diaza-cyclopenta[a] indene 2e, and decahydro-5-oxa-2,7a-diazacyclopenta[a]indene 2f as a result of 1,3-dipolar cycloaddition. In a similar reaction with 3-allylsulfanyl-2-arylazo- 3-(1-azacycloalk-1-yl)acrylonitriles 3, dipolar cycloaddition and intramolecular cyclization competed to give a mixture of compounds 2 (major products) and 1,4,6,7,8,8a-hexahydropyrrolo[2,1-c]-1,2,4-triazines 4b-d, 1,6,7,8,9,9a- hexahydro-4H-pyrido[2,1-c]-1,2,4-triazine 4e, and 1,4,6,7,9,9a-hexahydro-1,4- oxazino[3,4-c]-1,2,4-triazine 4f (minor products). © 2010 Springer Science+Business Media, Inc.

Author keywords:

1,2-diaza-1,3-butadienes; 1,3-dipolar cycloaddition; intramolecular cyclization; maleimide; morpholine; piperidine; pyrrolidine

Index keywords:

нет данных

DOI:

10.1007/s11172-010-0169-1

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-77958557503&doi=10.1007%2fs11172-010-0169-1&partnerID=40&md5=01bface477d2927f3a4e45f2689034bc

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-77958557503&doi=10.1007%2fs11172-010-0169-1&partnerID=40&md5=01bface477d2927f3a4e45f2689034bc
Affiliations	First Russian President B. N. el'Tsin Ural State Technical University, 19 ul. Mira, Ekaterinburg 620002, Russian Federation; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences, 20 ul. S. Kovalevskoi, Ekaterinburg 620041, Russian Federation
Author Keywords	1,2-diaza-1,3-butadienes; 1,3-dipolar cycloaddition; intramolecular cyclization; maleimide; morpholine; piperidine; pyrrolidine
References	Attanasi, O.A., De Crescentini, L., Filippone, P., Mantel-Lini, F., Perrulli, R., Santeusanio, S., (2002) ARKIVOC, p. 274; Deryabina, T.G., Belskaia, N.P., Kodess, M.I., Dehaen, W., Toppet, S., Bakulev, V.A., [3+2]- Versus [4+2]-cycloaddition reactions of 3-methylsulfanyl-2- arylazo- 3-(pyrrolidin-1-yl)acrylonitriles with N-substituted maleimides involving pyrrolidine-derived azomethine ylides (2006) Tetrahedron Letters, 47 (11), pp. 1853-1855. , DOI 10.1016/j.tetlet.2005.12.130, PII S0040403906000463; Belskaia, N.P., Deryabina, T.G., Koksharov, A.V., Kodess, M.I., Dehaen, W., Lebedev, A.T., Bakulev, V.A., A novel approach to fused 1,2,4-triazines by intramolecular cyclization of 1,2-diaza-1,3-butadienes bearing allyl(propargyl)sulfanyl and cyclic tert-amino groups (2007) Tetrahedron Letters, 48 (52), pp. 9128-9131. , DOI 10.1016/j.tetlet.2007.10.140, PII S0040403907021557; Sheldrick, G.M., (1997) SHELXS97, Program for the Solution of Crystal Structure, , University of Göttingen, Göttingen Germany; Sheldrick, G.M., (1997) SHELXL97, Program for the Refinement of Crystal Structure, , University of Göttingen, Göttingen Germany
Correspondence Address	Belskaya, N. P.; First Russian President B. N. el'Tsin Ural State Technical University, 19 ul. Mira, Ekaterinburg 620002, Russian Federation; email: belska@mail.ustu.ru
Language of Original Document	English
Abbreviated Source Title	Russ. Chem. Bull.
Source	Scopus