Study of direction of cyclization of malonodithioamides as a method of investigation of reactivity of α-diazothioacetamides / Dankova E.F., Bakulev V.A., Morzherin Yu.Yu. // Chemistry of Heterocyclic Compounds. - 1992. - V. 28, l. 8. - P. 931-936.

ISSN:

00093122

Type:

Article

Abstract:

The reaction of malonothioamides with benzene-sulfonyl azide and 2-azido-3-ethylbenzthiazolium tetrafluoroborate gave amides of 2-diazothiomalonic acid, which underwent cyclization to a mixture of 5-N-R-amino-1,2,3-thiadiazole-4-carbothioamides and 5-amino-1,2,3-thiadiazole-4-N-R-carbothioamides. The ratio of the isomeric thiadiazoles formed in this reaction is the same as in the reactions of 2-diazo-2-cyanoacetamides, 5-amino-1,2,3-thiadiazole- and 5-mercapto-1,2,3-triazole-4-carboxamides with P4S10 and of 5-amino-1, 2,3-thiadiazole-4-carbonitriles with H2S; it is characteristic of the influence of substituents on the reactivity of α-diazothioacetamides. It was found that the cyclization of the diazo compounds is accelerated when electron-acceptor substituents are attached to the nitrogen atom of the carbothioamide group. © 1993 Plenum Publishing Corporation.

Author keywords:

Index keywords:

нет данных

DOI:

10.1007/BF00531330

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https://www.scopus.com/inward/record.uri?eid=2-s2.0-34250084293&doi=10.1007%2fBF00531330&partnerID=40&md5=2e38a9e5f809e37a02f641b2095c5172

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-34250084293&doi=10.1007%2fBF00531330&partnerID=40&md5=2e38a9e5f809e37a02f641b2095c5172
Affiliations	S. M. Kirov Ural' Polytechnical Institute, Ekaterinburg, 620002, Russian Federation
References	L'abbe, G., Molecular rearrangements of five-membered ring heteromonocycles (1984) Journal of Heterocyclic Chemistry, 21, p. 627; Bakulev, V.A., Mokrushin, V.S., (1986) Khim. Geterotsikl. Soedin., 8, p. 1011; Pannel, K.H., Maye, A.J., Veer, Transition metal heterocyclic chemistry. 7. Stabilization of an .alpha.-diazo thioketone (a new class of compound) by a unique linear triiron cluster (1983) Journal of the American Chemical Society, 105 (19), p. 6186; Bakulev, V.A., Dankova, E.F., Mokrushin, V.S., Sidorov, E.O., Lebedev, A.T., (1987) Khim. Geterotsikl. Soedin., 6, p. 845; Dankova, E.F., Bakulev, V.A., Kolobov, Shishkina, V.I., Lebedev, A.T., (1988) Khim. Geterotsikl. Soedin., 9, p. 1269; Dankova, E.F., Bakulev, V.A., Kolobov, Andosova, G.V., Mokrushin, V.S., (1989) Khim. Geterotsikl. Soedin., 6, p. 827; E. F. Dankova and O. Yu. Krupina, in: 11th Conference of Young Scientists of the Bashkir Scientific Center of the Ural Branch of the Academy of Sciences of the USSR — Summaries of Lectures, Ufa (1987), p. 92; Goerdeler, H., Gnad, G., Über 5-Amino-1.2.3-thiadiazole (1966) Chemische Berichte, 99, p. 1618; Taylor, E.C., Zoltewicz, J.A., (1960) J. Am. Chem. Soc., 8 (10), p. 2659; Cowa, M.P., Leninson, M.I., (1985) Tetrahedron, 41 (22), p. 5061
Correspondence Address	Dankova, E.F.; S. M. Kirov Ural' Polytechnical Institute, Ekaterinburg, 620002, Russian Federation
Publisher	Kluwer Academic Publishers-Plenum Publishers
CODEN	CHCCA
Language of Original Document	English
Abbreviated Source Title	Chem Heterocycl Compd
Source	Scopus