Highly regio- and stereoselective addition of aminoenones to 2-substituted 3-nitro-2H-chromenes. Unexpected synthesis of 5-(trifluoromethyl)-5H-chromeno{[}3,4-b]pyridines / Korotaev Vladislav Yu.,Barkov Alexey Yu.,Kutyashev Igor B.,Kotovich Ivan V.,Ezhikova Marina A.,Kodess Mikhail I.,Sosnovskikh Vyacheslav Ya. // TETRAHEDRON. - 2015. - V. 71, l. 18. - P. 2658-2669.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

Reactions of 2-R-3-nitro-2H-chromenes (R=CF3, CCl3, Ph) with aminoenones derived from acetylacetone and cyclic amines (morpholine, piperidine) proceed diastereoselectively to give mainly cis-trans-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, 4-acetoacetonyl-3-nitrochromanes and 5H-chromeno{[}3,4-b]pyridines, depending on the substituent at the 2-position, were obtained in moderate to good yields. Similar results, except for the synthesis of 5H-chromeno{[}3,4-b] pyridines, were obtained by replacing acetylacetone with benzoylacetone. The stereochemistry of the products was established by X-ray diffraction analysis. (C) 2015 Elsevier Ltd. All rights reserved.

Author keywords:

3-Nitro-2H-chromenes; Push-pull enamines; Michael addition; Stereoselectivity; Chromanes; Chromeno{[}3,4-b]pyridines POTASSIUM CHANNEL ACTIVATORS; ANTIHYPERTENSIVE ACTIVITY; N-NUCLEOPHILES; S-NUCLEOPHILES; 3-NITRO-2-(TRIFLUOROMETHYL)-2H-CHROMENES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; CHEMISTRY; OXIDES; RING

DOI:

10.1016/j.tet.2015.03.041

Web of Science ID:

ISI:000353735200009

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY 6
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	POTASSIUM CHANNEL ACTIVATORS; ANTIHYPERTENSIVE ACTIVITY; N-NUCLEOPHILES; S-NUCLEOPHILES; 3-NITRO-2-(TRIFLUOROMETHYL)-2H-CHROMENES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; CHEMISTRY; OXIDES; RING
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vy.sosnovskikh@urfu.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-00179]; State Task from the Ministry of Education and Science of Russian Federation
Funding-Text	This work was supported financially by the Russian Foundation for Basic Research (Grant 14-03-00179) and performed within the State Task from the Ministry of Education and Science of Russian Federation.
Number-of-Cited-References	29
Usage-Count-Last-180-days	3
Usage-Count-Since-2013	18
Journal-ISO	Tetrahedron
Doc-Delivery-Number	CH0TL