Reaction of heterocyclic thioamides with dimethyl acetylenedicarboxylate. Synthesis of novel 2-azolyl-5-methoxycarbonylmethylene thiazolin-4-ones / Berseneva V.S., Morzherin Y.Y., Dehaen W., Luyten I., Bakulev V.A. // Tetrahedron. - 2001. - V. 57, l. 11. - P. 2179-2184.

ISSN:

00404020

Type:

Article

Abstract:

A systematic study of the reactions of dimethyl acetylenedicarboxylate (DMAD) with heterocyclic thioamides has been carried out and a number of new 2-isoxazolyl-(8), imidazolyl-(13a,b and 17a), 1,2,3-triazolyl-(13d,e) and 1,2,3-thiadiazolyl (17b) thiazolines have been prepared. The higher reactivity of the thioamide group in comparison with the amino group in these reactions has been established. © 2001 Elsevier Science Ltd.

Author keywords:

Dimethyl acetylene dicarboxylate; Thiazoline; Thioamides

Index keywords:

1,2,3 thiadiazolyl thiazoline; 2 (5 aminoimidazol 4 yl) 5 methoxycarbonylmethylenethiazolin 4 on; 2 (5 benzylmercaptoimidazol 4 yl) 5 methoxycarbonylmethylenethiazolin 4 on; 2 (5 ethylmercaptoimidazol

DOI:

10.1016/S0040-4020(01)00049-7

Смотреть в Scopus:

https://www.scopus.com/inward/record.uri?eid=2-s2.0-0035835954&doi=10.1016%2fS0040-4020%2801%2900049-7&partnerID=40&md5=7528241acb679a16c52150b6433cc423

Соавторы в МНС:

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Поле	Значение
Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0035835954&doi=10.1016%2fS0040-4020%2801%2900049-7&partnerID=40&md5=7528241acb679a16c52150b6433cc423
Affiliations	Department of Technology and Organic Synthesis, Urals State Technical University, 620002 Ekaterinburg, Russian Federation; Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
Author Keywords	Dimethyl acetylene dicarboxylate; Thiazoline; Thioamides
References	Vogeli, U., Von Philipsborn, W., Nagarajan, K., Nair, M.D., (1978) Helv. Chim. Acta, 61, p. 607; Acheson, R.M., Wallis, J.D., (1981) J. Chem. Soc., Perkin Trans 1, p. 415; Causs, V.Ya., Liepinsh, E.E., Calvinish, I.Ya., Lucevic, E.Ya., (1990) Khim. Geterosikl. Soedin., p. 120; Giammona, G., Neri, M., Carlisi, B., Pazzo, A., La Rosa, C., (1991) J. Heterocycl. Chem., 28, p. 325; Coen, S., Ragonnet, B., Vieillescazes, C., Roggero, J.P., (1985) Heterocycles, 23, p. 1225; Berseneva, V.S., Birucheva, N.Yu., Bakulev, V.A., (1993) Khim. Geterosikl. Soedin., p. 1688; Berseneva, V.S., Tkachev, A.V., Morzherin, Yu.Yu., Dehaen, W., Luyten, I., Bakulev, V.A., (1998) J. Chem. Soc., Perkin Trans 1, p. 2133; George, M.V., Khetan, S.K., Gupta, R.K., (1976) Adv. Heterocycl. Chem., 19, p. 279; Renzi, G., Dal Piaz, V., Pinzandi, S., (1969) Gazz. Chem. Ital., 99, p. 753; Ofitserov, V.I., Mokrushin, V.S., Nifontov, V.I., Pushkareva, Z.V., Nikiforova, N.V., Lych, L.N., (1975) Khim. Geterosikl. Soedin., p. 1550; Bakulev, V.A., Lebedev, A.T., Dankova, E.F., Mokrushin, V.S., Petrosyan, V.S., (1989) Tetrahedron, 45, p. 7329
Correspondence Address	Bakulev, V.A.; Dept. of Technol./Organic Synthesis, Urals State Technical University, 620002 Ekaterinburg, Russian Federation; email: wim.dehaen@chem.kuleuven.ac.be
CODEN	TETRA
Language of Original Document	English
Abbreviated Source Title	Tetrahedron
Source	Scopus