Domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylalkylidene)malononitriles: synthesis of functionalized 6-(trifluoromethyl)-6H-dibenzo{[}b,d]pyrans and a rare case of {[}1,5] sigmatropic shift of the nitro group / Korotaev Vladislav Yu,Barkov Alexey Yu,Sosnovskikh Vyacheslav Ya // TETRAHEDRON. - 2013. - V. 69, l. 46. - P. 9642-9647.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

A variety of functionalized 6-(trifluoromethyl)-6H-dibenzo{[}b,d]pyrans were easily synthesized in good yields under mild conditions by a domino reaction of 3-nitro-2-(trifluoromethyl)-2H-chromenes with 2-(1-phenylethylidene)- and 2-(1-phenylpropylidene)malononitriles. In the latter case, intermediate 7-amino-10-methyl-10-nitro-9-phenyl-6-(trifluoromethyl)-10,10a-dihydro-6 H-benzo{[}c]chromene-8-carbonitriles were isolated as a result of a rare {[}1,5] sigmatropic shift of the nitro group. (c) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

3-Nitro-2-(trifluoromethyl)-2H-chromenes; 1,1-Dicyanoolefins; 6-(Trifluoromethyl)-6H-dibenzo{[}b,d]pyrans; Domino reaction; {[}1,5] Sigmatropic nitro-shift PENTACYCLIC LAMELLARIN SKELETON; IPSO-NITRATION; 2-POLYFLUOROALKYLCHROMONES; REARRANGEMENT; DERIVATIVES; ROUTE; SALICYLALDEHYDES; CANNABINOIDS; ANALOGS

DOI:

10.1016/j.tet.2013.09.031

Web of Science ID:

ISI:000326768800016

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV 18
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	PENTACYCLIC LAMELLARIN SKELETON; IPSO-NITRATION; 2-POLYFLUOROALKYLCHROMONES; REARRANGEMENT; DERIVATIVES; ROUTE; SALICYLALDEHYDES; CANNABINOIDS; ANALOGS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vyacheslav.sosnovskikh@usu.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}11-03-00126-a]
Funding-Text	This work was financially supported by the Russian Foundation for Basic Research (Grant 11-03-00126-a).
Number-of-Cited-References	35
Usage-Count-Since-2013	20
Journal-ISO	Tetrahedron
Doc-Delivery-Number	249HR