Stereoselective addition of ethyl 3-morpholino(piperidino)-crotonates to 2-trihalomethyl-3-nitro-2H-chromenes. Synthesis of 4-acetonyl-3-nitrochromans / Korotaev Vladislav Yu.,Kutyashev Igor B.,Barkov Alexey Yu.,Sosnovskikh Vyacheslav Ya. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2015. - V. 51, l. 5. - P. 440-446.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

Tertiary enamines of acetoacetic ester, obtained with morpholine and piperidine, add to 2-R-1-3-nitro-2De-chromenes (R-1 = CF3, CCl3, Ph) via the vinylogue beta-methyl group and give the respective cis,trans-2,3,4-trisubstituted chromans, the stereoconfiguration of which was established by X-ray structural analysis. Acidic hydrolysis of these compounds was accompanied by decarboxylation and produced 4-acetonyl-3-nitrochromans with retention of configuration.

Author keywords:

chromans; 3-nitro-2H-chromenes; push-pull enamines; hydrolysis; stereochemistry POTASSIUM CHANNEL ACTIVATORS; PUSH-PULL ENAMINES; 2,3,4-TRISUBSTITUTED CHROMANES; ANTIHYPERTENSIVE ACTIVITY; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; 3-NITRO-2-(TRIFLUOROMETHYL)-2H-CHROMENES; 3-NITRO-2H-CHROMENES

DOI:

10.1007/s10593-015-1718-1

Web of Science ID:

ISI:000358138200004

Соавторы в МНС:

Другие поля

Поле	Значение
Month	MAY
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	POTASSIUM CHANNEL ACTIVATORS; PUSH-PULL ENAMINES; 2,3,4-TRISUBSTITUTED CHROMANES; ANTIHYPERTENSIVE ACTIVITY; N-NUCLEOPHILES; C-NUCLEOPHILES; S-NUCLEOPHILES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; 3-NITRO-2-(TRIFLUOROMETHYL)-2H-CHROMENES; 3-NITRO-2H-CHROMENES
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]
Funding-Text	The results of this work were obtained within the framework of fulfilling the State Assignment of the Ministry of Education and Science of Russia, with partial financial support from the Russian Foundation for Basic Research (project No. 14-03-00179).
Number-of-Cited-References	26
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	5
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	CN0XN