The reaction of 6-substituted 4-pyrone-2-carboxylic acids with o-phenylenediamine. Synthesis and structure of 3-(1H-1,5-benzodiazepin-2(3H)-ylidenemethyl)quinoxalin-2(1H)-ones / Obydennov Dmitrii L.,Sosnovskikh Vyacheslav Ya. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2015. - V. 51, l. 3. - P. 281-290.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

{[}GRAPHICS] 6-Aryl(alkyl)-4-pyrone-2-carboxylic acids upon refluxing in n-BuOH react with two equivalents of.-phenylenediamine, giving 26-85\% yields of 3-(1H-1,5-benzodiazepin-2(3H)-ylidenemethyl)quinoxalin-2(1H)-ones, which exist in two tautomeric forms. The direction of the initial nucleophilic attack on the pyrone ring and the tautomeric composition of the obtained products is mainly determined by the substituent at the.-6 atom. Quantum-chemical calculations were used to estimate the stability of tautomers in the gas phase.

Author keywords:

1,5-benzodiazepines; comanic acids; o-phenylenediamine; 4-pyrones; quinoxalin-2-ones; tautomerism MICROWAVE-ASSISTED SYNTHESIS; QUINOXALINONE DERIVATIVES; HINSBERG REACTION; CHELIDONIC ACID; REGIOSELECTIVE SYNTHESIS; NUCLEOPHILIC-REAGENTS; FLUORO ORGANICS; 1ST SYNTHESIS; HETEROCYCLES; FACILE

DOI:

10.1007/s10593-015-1696-3

Web of Science ID:

ISI:000354479700012

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAR
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	MICROWAVE-ASSISTED SYNTHESIS; QUINOXALINONE DERIVATIVES; HINSBERG REACTION; CHELIDONIC ACID; REGIOSELECTIVE SYNTHESIS; NUCLEOPHILIC-REAGENTS; FLUORO ORGANICS; 1ST SYNTHESIS; HETEROCYCLES; FACILE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	dobydennov@mail.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-31925]
Funding-Text	This work received financial support from the Russian Foundation for Basic Research (grant 14-03-31925).
Number-of-Cited-References	73
Usage-Count-Since-2013	7
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	CI1CW