Synthesis of 5-(trifluoromethyl)-5H-chromeno{[}3,4-b]pyridines from 3-nitro-2-(trifluoromethyl)-2H-chromenes and aminoenones derived from acetylacetone and cyclic amines / Korotaev Vladislav Yu.,Barkov Alexey Yu.,Sosnovskikh Vyacheslav Ya. // TETRAHEDRON LETTERS. - 2013. - V. 54, l. 24. - P. 3091-3093.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Reactions of 3-nitro-2H-chromenes with aminoenones derived from acetylacetone and cyclic amines proceed diastereoselectively to give functionalized 2,3,4-trisubstituted chromanes as a result of nucleophilic addition of the vinylogous beta-methyl group at the C-4 atom of the chromene system. From these compounds, under acidic conditions, 5-(trifluoromethyl)-5H-chromeno{[}3,4-b]pyridines and 4-acetoacetonyl-3-nitro-2-(trichloromethyl/phenyl)chromanes, depending on the substituent at the 2-position, were obtained in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

3-Nitro-2H-chromenes; Push-pull enamines; Michael addition; Chromanes; Chromeno{[}3,4-b]pyridines PENTACYCLIC LAMELLARIN SKELETON; POTASSIUM CHANNEL ACTIVATORS; STEREOSELECTIVE-SYNTHESIS; ANTIHYPERTENSIVE ACTIVITY; MICHAEL ADDITION; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; CHROMENES

DOI:

10.1016/j.tetlet.2013.03.137

Web of Science ID:

ISI:000319645100016

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JUN 12
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	PENTACYCLIC LAMELLARIN SKELETON; POTASSIUM CHANNEL ACTIVATORS; STEREOSELECTIVE-SYNTHESIS; ANTIHYPERTENSIVE ACTIVITY; MICHAEL ADDITION; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; CHROMENES
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]
Funding-Text	This work was supported financially by the Russian Foundation for Basic Research (Grant 11-03-00126).
Number-of-Cited-References	34
Usage-Count-Since-2013	12
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	154AY