Substituted chromones in {[}3+2] cycloadditions with nonstabilized azomethine ylides: synthesis of 1-benzopyrano{[}2,3-c]pyrrolidines and 1-benzopyrano{[}2,3-c:3,4-c `]dipyrrolidines / Sosnovskikh Vyacheslav Y.,Kornev Mikhail Y.,Moshkin Vladimir S.,Buev Evgeny M. // TETRAHEDRON. - 2014. - V. 70, l. 48. - P. 9253-9261.

ISSN/EISSN:

0040-4020 / нет данных

Type:

Article

Abstract:

Chromones bearing electron-withdrawing substituents at the 2- or 3-position react with nonstabilized azomethine ylides to produce 1-benzopyrano{[}2,3-c]pyrrolidines in good yields. Reactions of 3cyanochromones proceed diastereoselectively to give 1-benzopyrano{[}2,3-c]pyrrolidines and tetrahydro-1H-spiro{[}chromeno{[}2,3-c]pyrrol-9,5'-oxazolidine]-9a-carbo nitriles, depending on the reactant ratio, as a result of a 1,3-dipolar cycloaddition of the azomethine ylide at the double bond and carbonyl group of the chromone system. The latter undergoes demethylenation and recyclization into a novel hexahydrochromeno{[}2,3-c:3,4-c']dipyrrole tetracyclic system on heating with hydrochloric acid. (C) 2014 Elsevier Ltd. All rights reserved.

Author keywords:

Chromones; Azomethine ylide; {[}3+2] Cycloaddition; Benzopyrano{[}2,3-c]pyrrolidines; Recyclization; Hexahydrochromeno{[}2,3-c:3,4-c `]dipyrroles ALPHA-AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION; DECARBOXYLATIVE TRANSAMINATION; 3-NITROCHROMENE DERIVATIVES; INDOLIZIDINE ALKALOIDS; RECEPTOR ANTAGONISTS; AROMATIC-ALDEHYDES; MECHANISM; ROUTE; ISOELAEOCARPINE

DOI:

10.1016/j.tet.2014.09.090

Web of Science ID:

ISI:000345492200012

Соавторы в МНС:

Другие поля

Поле	Значение
Month	DEC 2
Publisher	PERGAMON-ELSEVIER SCIENCE LTD
Address	THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND
Language	English
Keywords-Plus	ALPHA-AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITION; DECARBOXYLATIVE TRANSAMINATION; 3-NITROCHROMENE DERIVATIVES; INDOLIZIDINE ALKALOIDS; RECEPTOR ANTAGONISTS; AROMATIC-ALDEHYDES; MECHANISM; ROUTE; ISOELAEOCARPINE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vy.sosnovskikh@urfu.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement	Russian Science Foundation {[}14-13-00388]
Funding-Text	This work was financially supported by the Russian Science Foundation (Grant 14-13-00388) and carried out under the terms of the Ural Federal University development program with the financial support of young scientists.
Number-of-Cited-References	51
Usage-Count-Last-180-days	5
Usage-Count-Since-2013	26
Journal-ISO	Tetrahedron
Doc-Delivery-Number	AU3DF