Synthesis of chromeno{[}3,4-c]{[}1,2]oxazine-N-oxides via formal {[}4+2] cycloaddition of 3-nitro-2-trihalomethy1-2H-chromenes with cyclohexanone and pinacolone enamines / Korotaev Vladislav Yu,Barkov Alexey Yu,Matochkina Evgeniya G.,Kodess Mikhail I.,Sosnovskikh Vyacheslav Ya // TETRAHEDRON. - 2014. - V. 70, l. 34. - P. 5161-5167.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

3-Nitro-2-trichloro(trifluoro)methyl-2H-chromenes undergo a formal {[}4+2] cycloaddition reaction to cyclohexanone and pinacolone enamines, producing chromeno{[}3,4-c]{[}1,2]benzoxazin-6-oxides with high diastereoselectivity and in good yields. In addition, some novel 2,3,4-trisubstituted chromanes were obtained. The stereochemistry of the products was established based on a 2D NOESY experiment and an X-ray diffraction study. (C) 2014 Elsevier Ltd. All rights reserved.

Author keywords:

3-Nitro-2-trihalomethyl-2H-chromenes; Enamines; Cyclic nitronates; 2,3,4-Trisubstituted chromanes; Stereoselectivity POTASSIUM CHANNEL ACTIVATORS; 1,3-DIPOLAR CYCLOADDITIONS; SUBSTITUTED PTEROCARPANS; 3-NITROCHROMENE DERIVATIVES; ANTIHYPERTENSIVE ACTIVITY; REGIOSELECTIVE SYNTHESIS; AZOMETHINE YLIDES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; NUCLEOPHILES; RING

DOI:

10.1016/j.tet.2014.05.100

Web of Science ID:

ISI:000339035200020

Соавторы в МНС:

Другие поля

Поле	Значение
Month	AUG 26
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	POTASSIUM CHANNEL ACTIVATORS; 1,3-DIPOLAR CYCLOADDITIONS; SUBSTITUTED PTEROCARPANS; 3-NITROCHROMENE DERIVATIVES; ANTIHYPERTENSIVE ACTIVITY; REGIOSELECTIVE SYNTHESIS; AZOMETHINE YLIDES; 3-NITRO-2-TRIHALOMETHYL-2H-CHROMENES; NUCLEOPHILES; RING
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	sosn1951@mail.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	This work was financially supported by the Russian Foundation for Basic Research (Grant 14-03-00179).
Number-of-Cited-References	39
Usage-Count-Since-2013	17
Journal-ISO	Tetrahedron
Doc-Delivery-Number	AL3NK