Synthesis of 3-(trifluoromethyl)indeno{[}2,1-c]pyran-1,9-diones from 4-aryl-3-carbethoxy-6-(trifluoromethyl)-2-pyrones and their reaction with sodium azide leading to new carbostyril derivatives / Usachev Sergey A.,Usachev Boris I.,Sosnovskikh Vyacheslav Ya // TETRAHEDRON. - 2014. - V. 70, l. 1. - P. 60-66.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

Treatment of ethyl 4-aryl-6-(trifluoromethyl)-2-oxo-2H-pyran-3-carboxylates, prepared from 4,4,4-trifluorobutane-1,3-diones, PCl5 and sodium diethyl malonate, with sulfuric acid afforded the intramolecular Friedel Crafts acylation products, 3-(trifluoromethyl)indeno{[}2,1-c]pyran-1,9-diones, from which 2-(trifluoromethyl)-6H-pyrano{[}3,4-c]quinoline-4,5-diones were obtained via the Schmidt reaction in moderate yields. The latter reacted with sodium azide to give 2-oxo-4-(5-trifluoromethyl-1,2,3-triazol-4-yl)-1,2-dihydroquinoline-3-ca rboxylic acids in good yields. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

2-Pyrones; Friedel-Crafts acylation; Indeno{[}2,1-c]pyran-1,9-diones; Schmidt reaction; Pyrano{[}3,4-c]quinoline-4,5-diones; Triazoles; Trifluoromethylated heterocycles SCHMIDT REACTION; ISOQUINOLINE DERIVATIVES; 6-(TRIFLUOROMETHYL)COMANIC ACID; CONVENIENT SYNTHESIS; CATALYZED ADDITIONS; ORGANIC POLYHALIDES; 2-POLYFLUOROALKYLCHROMONES; CONVERSION; QUINOLINE; INDONES

DOI:

10.1016/j.tet.2013.11.033

Web of Science ID:

ISI:000330097500008

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN 7
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	SCHMIDT REACTION; ISOQUINOLINE DERIVATIVES; 6-(TRIFLUOROMETHYL)COMANIC ACID; CONVENIENT SYNTHESIS; CATALYZED ADDITIONS; ORGANIC POLYHALIDES; 2-POLYFLUOROALKYLCHROMONES; CONVERSION; QUINOLINE; INDONES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vyacheslav.sosnovskikh@usu.ru
ResearcherID-Numbers	Usachev, Sergey/N-2942-2016
Number-of-Cited-References	48
Usage-Count-Last-180-days	3
Usage-Count-Since-2013	28
Journal-ISO	Tetrahedron
Doc-Delivery-Number	295DT