Synthesis of trans,trans-2,3,4-trisubstituted chromans from 3-nitro-2H-chromenes and enamines of acetoacetic ester and acetylacetone. A new type of configurationally stable atropisomers / Korotaev Vladislav Yu.,Barkov Alexey Yu.,Ezhikova Marina A.,Kodess Mikhail I.,Sosnovskikh Vyacheslav Ya. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2015. - V. 51, l. 6. - P. 531-540.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

Enamines of acetoacetic ester and acetylacetone added at the activated double bond of 2-R-1-3-nitro-2De-chromenes (R-1 = CF3, CCl3, Ph) with their central alpha-D atoms, forming trans,trans-2,3,4-trisubstituted chromans. The adducts obtained from acetylacetone enamines represented mixtures of comparable amounts of configurationally stable atropisomers, the formation of which was connected with hindered rotation around the C(sp (3))-C(sp (2)) bond. A reaction with enamines of acetoacetic ester led practically exclusively to a single anti atropisomer.

Author keywords:

chromans; 3-nitro-2H-chromenes; push-pull enamines; atropisomerism; nucleophilic addition POTASSIUM CHANNEL ACTIVATORS; ANTIHYPERTENSIVE ACTIVITY; STEREOSELECTIVE ADDITION; MICHAEL ADDITION; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; ISOMERS; SYSTEM

DOI:

10.1007/s10593-015-1733-2

Web of Science ID:

ISI:000359431000005

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	POTASSIUM CHANNEL ACTIVATORS; ANTIHYPERTENSIVE ACTIVITY; STEREOSELECTIVE ADDITION; MICHAEL ADDITION; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; ISOMERS; SYSTEM
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	nmr@ios.uran.ru 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]
Funding-Text	The results of this work were obtained within the framework of State Assignment by the Ministry of Education and Science of the Russian Federation with partial financial support from the Russian Foundation for Basic Research (project No. 14-03-00179).
Number-of-Cited-References	33
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	9
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	CO8OZ