3-Cyanochromones in {[}3+2] cycloadditions with an azomethine ylide crossMark derived from sarcosine and formaldehyde. A short synthesis of 1-benzopyrano {[}2,3-c:3,4-c `] dipyrrolidines / Sosnovskikh Vyacheslav Ya.,Kornev Mikhail Yu.,Moshkin Vladimir S. // TETRAHEDRON LETTERS. - 2014. - V. 55, l. 1. - P. 212-214.

ISSN/EISSN:

0040-4039 / нет данных

Type:

Article

Abstract:

Reactions of 3-cyanochromones with sarcosine and paraformaldehyde 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 intermediate nonstabilized azomethine ylide at the double bond and carbonyl group of the chromone system. The latter undergoes demethylenation and recyclization into a novel hexahydrochromeno{[}2,3c:3,4-c']dipyrrole tetracyclic system on heating with hydrochloric acid. (C) 2013 Elsevier Ltd. All rights reserved.

Author keywords:

3-Cyanochromones; Nonstabilized azomethine ylide; {[}3+2] Cycloaddition; 1-Benzopyrano{[}2,3-c]pyrrolidines; Recyclization; Hexahydrochromeno{[}2,3-c:3,4-c `]dipyrroles ALPHA-AMINO-ACIDS; 1,3-DIPOLAR CYCLOADDITIONS; DECARBOXYLATIVE TRANSAMINATION; 3-NITROCHROMENE DERIVATIVES; 3-SUBSTITUTED COUMARINS; MECHANISM; ROUTE; 2-PI-COMPONENTS

DOI:

10.1016/j.tetlet.2013.10.154

Web of Science ID:

ISI:000329960500046

Соавторы в МНС:

Другие поля

Поле	Значение
Month	JAN 1
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 CYCLOADDITIONS; DECARBOXYLATIVE TRANSAMINATION; 3-NITROCHROMENE DERIVATIVES; 3-SUBSTITUTED COUMARINS; MECHANISM; ROUTE; 2-PI-COMPONENTS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vyacheslav.sosnovskikh@usu.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017
Funding-Acknowledgement	RFBR {[}12-03-31036]
Funding-Text	This work was supported financially by the RFBR (Grant 12-03-31036).
Number-of-Cited-References	33
Usage-Count-Last-180-days	2
Usage-Count-Since-2013	20
Journal-ISO	Tetrahedron Lett.
Doc-Delivery-Number	293GX