Reactions of Malonothioamide Derivatives with Azides / Dianova L. N.,Berseneva V. S.,El'tsov O. S.,Fan Z. -J.,Bakulev V. A. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2014. - V. 50, l. 7. - P. 972-978.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

The reactions of primary and tertiary malonothioamides with aryl and sulfonyl azides can take place in three directions, depending on the nature of the thioamides and azides. Ethoxycarbonylthioacetamide reacts with aryl azides with the formation of ethyl 5-amino-1-aryl-1,2,3-triazole-4-carboxylates. In reaction with aryl azides tertiary thioamides of cyanoacetic acid form 5-amino-1-aryl-1,2,3-triazole-4-carbothioamides, and in reaction with tosyl azide they form 5-amino-4-carboxamidino-1,2,3-thia-diazoles. Hypothetical mechanisms for the transformations are discussed.

Author keywords:

aryl azides; malonothioamides; 1,2,3-thiadiazoles; 1,2,3-triazoles; cyclocondensation; rearrangements 1,2,3-TRIAZOLES; REARRANGEMENTS; CYCLIZATION; INHIBITORS

DOI:

10.1007/s10593-014-1552-x

Web of Science ID:

ISI:000344092000007

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	1,2,3-TRIAZOLES; REARRANGEMENTS; CYCLIZATION; INHIBITORS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	fanzj@nankai.edu.cn v.a.bakulev@urfu.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-01033]; Foundation of China {[}21372132]; International Science \& Technology Cooperation Program of China {[}2014DFR41030]
Funding-Text	The work was carried out with financial support from the Russian Foundation for Basic Research (grant 14-03-01033), the Foundation of China (21372132), and the International Science \& Technology Cooperation Program of China (2014DFR41030).
Number-of-Cited-References	27
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	12
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	AS2EG