Stereoselective hetero-Diels-Alder reaction of 3-nitro-2-trihalomethyl-2H-chromenes with 2,3-dihydrofuran and ethyl vinyl ether under solvent-free conditions / Korotaev Vladislav Yu.,Sosnovskikh Vyacheslav Ya.,Barabanov Mikhail A.,Yasnova Evgeniya S.,Ezhikova Marina A.,Kodess Mikhail I.,Slepukhin Pavel A. // TETRAHEDRON. - 2010. - V. 66, l. 6. - P. 1404-1409.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

3-Nitro-2-trifluoro(trichloro)methyl-2H-chromenes undergo heterodiene cycloaddition to 2,3-chhydrofuran and ethyl vinyl ether under solvent-free conditions producing novel cyclic nitronates with high stereoselectivity and in good yields 3,6-Dinitro-2-trifluoromethy-2H-chromene reacts with two molecules of ethyl vinyl ether to give the tandem {[}4+2]/{[}3+2] cycloaddition adduct in 48\% yield The stereochermstry of the products was established based on 2D COSY, NOESY, HSQC, and HMBC experiments and an X-ray diffraction study (C) 2009 Elsevier Ltd All rights reserved

Author keywords:

3-Nitro-2-trihalomethyl-2H-chromenes; Enol ethers; Hetero-Diels-Alder reaction; 1,3-Dipolar cycloaddition; NMR spectroscopy; X-ray diffraction study POTASSIUM CHANNEL ACTIVATORS; 3+2 CYCLOADDITION REACTIONS; 1,3-DIPOLAR CYCLOADDITIONS; SUBSTITUTED PTEROCARPANS; 3-NITROCHROMENE DERIVATIVES; REGIOSELECTIVE SYNTHESIS; AZOMETHINE YLIDES; N-NUCLEOPHILES; S-NUCLEOPHILES; DISCOVERY

DOI:

10.1016/j.tet.2009.11.094

Web of Science ID:

ISI:000274591900035

Соавторы в МНС:

Другие поля

Поле	Значение
Month	FEB 6
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	POTASSIUM CHANNEL ACTIVATORS; 3+2 CYCLOADDITION REACTIONS; 1,3-DIPOLAR CYCLOADDITIONS; SUBSTITUTED PTEROCARPANS; 3-NITROCHROMENE DERIVATIVES; REGIOSELECTIVE SYNTHESIS; AZOMETHINE YLIDES; N-NUCLEOPHILES; S-NUCLEOPHILES; DISCOVERY
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
ResearcherID-Numbers	Korotaev, Vladislav/L-2692-2016
ORCID-Numbers	Korotaev, Vladislav/0000-0002-7492-5116
Funding-Acknowledgement	Russian Foundation for Basic Research {[}06-03-04004]
Funding-Text	This work was financially Supported by the Russian Foundation for Basic Research (Grant 06-03-04004).
Number-of-Cited-References	29
Usage-Count-Since-2013	11
Journal-ISO	Tetrahedron
Doc-Delivery-Number	556LF