Synthesis of 4-aryl-6-methyl-7a-(trifluoromethyl)-2,4a,5,6,7,7a-hexahydropyrano{[}2,3 -c]pyrrol-2-ones from 4-aryl-6-(trifluoromethyl)-2-pyrones, sarcosine, and formaldehyde / Usachev Sergey A.,Popova Natal'ya V.,Moshkin Vladimir S.,Sosnovskikh Vyacheslav Ya. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2015. - V. 51, l. 10. - P. 913-917.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

4-Aryl-6-(trifluoromethyl)-2-pyrones reacted with the nonstabilized azomethine ylide obtained from sarcosine and formaldehyde under reflux in benzene for 6 h, resulting in {[}3+2] cycloaddition that gave 4-aryl-6-methyl-7a-(trifluoromethyl)-2,4a, 5,6,7,7a-hexahydropyrano-{[}2,3-c]pyrrol-2-ones in 42-56\% yields. In the case of 4-aryl-3-carbethoxy-6-(trifluoromethyl)-2-pyrones, besides the respective pyrano{[} 2,3-c]pyrrolidines (66-71\% yields) also 4-aryl-1-methyl-2-(trifluoromethyl)pyrroles were isolated as minor products.

Author keywords:

azomethine ylides; pyrano{[}2,3-c]pyrrolidines; 2-pyrones; pyrroles; {[}3+2] cycloaddition NONSTABILIZED AZOMETHINE YLIDES; 1,3-DIPOLAR CYCLOADDITIONS; METHYL COUMALATE; SODIUM-AZIDE; DERIVATIVES; 2-PYRONES; PYRAN-2-ONES; 2-PYRIDONES; REACTIVITY; ACID

DOI:

10.1007/s10593-015-1795-1

Web of Science ID:

ISI:000369005600008

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	NONSTABILIZED AZOMETHINE YLIDES; 1,3-DIPOLAR CYCLOADDITIONS; METHYL COUMALATE; SODIUM-AZIDE; DERIVATIVES; 2-PYRONES; PYRAN-2-ONES; 2-PYRIDONES; REACTIVITY; ACID
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	vy.sosnovskikh@urfu.ru
ResearcherID-Numbers	Moshkin, Vladimir/E-6623-2017 Usachev, Sergey/N-2942-2016
Funding-Acknowledgement	Russian Scientific Fund {[}14-13-00388]
Funding-Text	This work was performed with financial support from the Russian Scientific Fund (project 14-13-00388).
Number-of-Cited-References	30
Usage-Count-Last-180-days	3
Usage-Count-Since-2013	7
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	DC1VL