Synthesis of Assemblies of Isoxazole and Azoles Based on 1,3-Dipolar Cycloaddition Reaction of Enamines with Nitrile Oxides / Efimov Ilya V.,Shafran Yuri M.,Volkova Natalia N.,Beliaev Nikolai A.,Slepukhin Pavel A.,Bakulev Vasiliy A. // CHEMISTRY OF HETEROCYCLIC COMPOUNDS. - 2016. - V. 52, l. 9. - P. 743-749.

ISSN/EISSN:

0009-3122 / 1573-8353

Type:

Article

Abstract:

2-(1,2,3-Thiadiazol-5-yl)enamines and 3-(1,2,3-triazol-4-yl)enaminones react with arylhydroxamoyl chlorides at room temperature with the exclusive formation of 3-aryl-4-(1,2,3-thiadiazol-5-yl)- and {[}4-(1,2,3-triazol-4-yl)carbonyl]isoxazoles in high yields. The proposed mechanism includes in situ generation of nitrile oxides, which participate in the (3+2)-dipolar cycloaddition reactions leading to the formation of the isoxazole ring.

Author keywords:

enamines; hydroxamoyl chlorides; isoxazoles; cycloaddition; regioselectivity ALLYL COMPOUNDS; DERIVATIVES; ACIDS; 1,2,3-TRIAZOLES; SELECTIVITY; INHIBITORS

DOI:

10.1007/s10593-016-1958-8

Web of Science ID:

ISI:000388588400019

Соавторы в МНС:

Другие поля

Поле	Значение
Month	SEP
Publisher	SPRINGER
Address	233 SPRING ST, NEW YORK, NY 10013 USA
Language	English
EISSN	1573-8353
Keywords-Plus	ALLYL COMPOUNDS; DERIVATIVES; ACIDS; 1,2,3-TRIAZOLES; SELECTIVITY; INHIBITORS
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	slepukhin@ios.uran.ru v.a.bakulev@urfu.ru
ResearcherID-Numbers	Efimov, Ilya/H-8741-2016
ORCID-Numbers	Efimov, Ilya/0000-0003-1123-987X
Funding-Acknowledgement	Russian Foundation for Basic Research {[}14-03-01033]; Ministry of Education and Science of the Russian Federation {[}4.1626.2014 / K]
Funding-Text	This work was supported financially by the Russian Foundation for Basic Research (grant 14-03-01033) and the Ministry of Education and Science of the Russian Federation (State assignment 4.1626.2014 / K).
Number-of-Cited-References	32
Usage-Count-Last-180-days	4
Usage-Count-Since-2013	9
Journal-ISO	Chem. Heterocycl. Compds.
Doc-Delivery-Number	ED1EV