3-(1H-1,5-Benzodiazepin-2(3H)-ylidenemethyl)-quinoxalin-2(1H)-ones in reactions with nucleophiles. Synthesis and structure of 3-(hetarylmethyl)quinoxalin-2-ones / Obydennov Dmitrii L.,Sosnovskikh Vyacheslav Ya. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2015. - V. 51, l. 6. - P. 503-513.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

3-(1De-1,5-Benzodiazepin-2(3De)-ylidenemethyl)quinoxalin-2(1H)-ones react with hydrazines and hydroxylamine in acidic medium, leading to conversion of seven-membered ring to five-membered ring and formation of the respective dihetarylmethanes in 40-79\% yields. The starting materials containing an electron-donating substituent (R = Ph, 4-ClC6H4, 2-naphthyl, 2-thienyl, Me) at position 4 of the benzodiazepine ring reacted predominantly at the D-4 atom, while another starting material containing an electron-withdrawing substituent (R = CF3) at the same position reacted at the D-2 atom. The synthesized 3-(hetarylmethyl)quinoxalin-2-ones existed in DMSO-d (6) solution as tautomeric imine and enamine forms, the ratio of which depended on the possibility of a strong intramolecular hydrogen bond and indicated regioselective formation of pyrazole or isoxazole rings. Acidic hydrolysis of the benzodiazepinD3/4quinoxaline system resulted in loss of the diazepine ring and formation of diketoquinoxalines in 41-82\% yields, having a different reactivity than their synthetically equivalent benzodiazepine analogs.

Author keywords:

1,5-benzodiazepines; isoxazoles; pyrazoles; quinoxalines; regioselectivity; tautomerism QUINOXALINONE DERIVATIVES; A INHIBITORS; (Z)-3-(QUINOLIN-2-YLMETHYLENE)-3,4-DIHYDROQUINOXALIN-2(1H)-ONE; HYDRAZINOLYSIS; CAROVERINE; MECHANISM; ESIPT; ACIDS

DOI:

10.1007/s10593-015-1729-y

Web of Science ID:

ISI:000359431000001

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	QUINOXALINONE DERIVATIVES; A INHIBITORS; (Z)-3-(QUINOLIN-2-YLMETHYLENE)-3,4-DIHYDROQUINOXALIN-2(1H)-ONE; HYDRAZINOLYSIS; CAROVERINE; MECHANISM; ESIPT; ACIDS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	dmitry.obydennov@urfu.ru
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-31925]
Funding-Text	This work was performed with financial support from the Russian Foundation for Basic Research (project No. 14-03-31925).
Number-of-Cited-References	31
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	7
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	CO8OZ