Tandem Knoevenagel Condensation and Intramolecular Cycloaddition Reactions of 2-Azidobenzaldehydes with 2-Cyanoacetamides in the Synthesis of 4-Thiocarbamoyltetrazolo-{[}1,5-a]Quinolines / Filimonov Valeriy O.,Abaev Vladimir T.,Beryozkina Tetyana V.,Galata Kristina A.,Slepukhin Pavel A.,Kostenko Maria A.,Berseneva Vera S. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2016. - V. 52, l. 9. - P. 721-726.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

The reaction of 2-azidobenzaldehydes with 2-thioamides of cyanoacetic acid proceeds without a solvent and base at 80-90A degrees C selectively by one of the possible routes to form tetrazolo{[}1,5-a]quinolines. The proposed mechanism of the reaction involves the Knoevenagel condensation and subsequent intramolecular {[}3+2] cycloaddition of the azide group at the CaeN bond of an intermediate acrylonitrile.

Author keywords:

2-azidobenzaldehydes; cyanoacetic acid thioamides; tetrazolo{[}1,5-a]quinoline; cycloaddition; cyclocondensation; structural isomers AZIDES; REARRANGEMENTS; DERIVATIVES; CYCLIZATION; INHIBITORS; THIOAMIDES; DIVERSITY

DOI:

10.1007/s10593-016-1954-z

Web of Science ID:

ISI:000388588400015

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	AZIDES; REARRANGEMENTS; DERIVATIVES; CYCLIZATION; INHIBITORS; THIOAMIDES; DIVERSITY
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	hampazero@mail.ru v.s.berseneva@urfu.ru
ORCID-Numbers	Filimonov, Valeriy/0000-0001-6067-7150
Funding-Acknowledgement	Russian Science Foundation {[}15-13-1003]
Funding-Text	This work was supported by the Russian Science Foundation (grant No15-13-1003).
Number-of-Cited-References	32
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	3
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	ED1EV