Reactions of 3-nitro-2-trihalomethyl-2H-chromenes with C-nucleophiles. Synthesis of 3-nitro-4-(pyrazol-4-yl)-2-trihalomethylchromanes / Korotaev V. Yu.,Sosnovskikh V. Ya.,Kutyashev I. B.,Kodess M. I. // RUSSIAN CHEMICAL BULLETIN. - 2006. - V. 55, l. 11. - P. 2020-2031.

ISSN/EISSN:

1066-5285 / нет данных

Type:

Article

Abstract:

The nucleophilic addition of acetylacetone and ethyl acetoacetate at the double bond of 3-nitro-2-trihalomethyl-2H-chromenes in the presence of NaH affords 2,3,4-trisubstituted chromanes containing the beta-dicarbonyl fragment at position 4. The trans-trans configuration and the enol structure of the reaction products were confirmed by H-1 NMR spectroscopy and X-ray diffraction. Treatment of these compounds with hydrazine gives the corresponding 3-nitro-4-(pyrazol-4-yl)-2-trihalomethylchromanes. The reactions of 3-nitro-2-trihalomethyl-2H-chromenes with nitromethane and nitroethane in the presence of K2CO3 produce 1,3-dinitro derivatives of the chromane series.

Author keywords:

chromenes; chromanes; nitro compounds; pyrazoles; Michael reaction; diastereomers; NMR spectroscopy; X-ray diffraction study POTASSIUM CHANNEL ACTIVATORS; MICHAEL ADDITION; ANTIHYPERTENSIVE ACTIVITY; 1,3-DICARBONYL COMPOUNDS; 3-NITROCHROMENES; NITROALKENES; NITROOLEFINS; DISCOVERY; RING

DOI:

10.1007/s11172-006-0546-y

Web of Science ID:

ISI:000245501600019

Соавторы в МНС:

Другие поля

Поле	Значение
Month	NOV
Publisher	SPRINGER
Address	233 SPRING STREET, NEW YORK, NY 10013 USA
Language	English
Keywords-Plus	POTASSIUM CHANNEL ACTIVATORS; MICHAEL ADDITION; ANTIHYPERTENSIVE ACTIVITY; 1,3-DICARBONYL COMPOUNDS; 3-NITROCHROMENES; NITROALKENES; NITROOLEFINS; DISCOVERY; RING
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Multidisciplinary
Author-Email	Vyacheslav.Sosnovskikh@usu.ru
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Number-of-Cited-References	26
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	5
Journal-ISO	Russ. Chem. Bull.
Doc-Delivery-Number	154IY