Reactions of beta-Azolylenamines with Sulfonyl Azides as an Approach to N-Unsubstituted 1,2,3-Triazoles and Ethene-1,2-diamines / Efimov Ilya,Bakulev Vasiliy,Beliaev Nikolai,Beryozkina Tetyana,Knippschild Uwe,Leban Johann,Zhi-Jin Fan,Eltsov Oleg,Slepukhin Pavel,Ezhikova Marina,Dehaen Wim // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2014. - V. 2014, l. 17. - P. 3684-3689.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

The reactions of beta-azolylenamines 1 with sulfonyl azides 2 in acetonitrile furnished 1H-4-(azol-5-yl)-1,2,3-triazoles 3 in yields of 52-93\%. beta-Benzoylenaminones and beta-nitroenamine of type 1 also reacted with tosyl azide to form the same type of products 3, proving the generality and efficiency of the method for the synthesis of N-unsubstituted 1,2,3-triazoles. On the other hand, the reactions of 3-(1-aryl-1,2,3-triazol-5-yl)enamines with tosyl azide in the absence of a solvent afforded a mixture of (E)-1-dimethylamino-2-tosylaminoethenes 5 and N,N-dimethyl-N'-tosylformamidine 6 in yields of 40-50 and 20\%, respectively. The formation of a variety of compounds from the reactions of enamines 1 with sulfonyl azides 2 is rationalized by the various possible transformations of the intermediate 5-dimethylamino-1,2,3-triazolines 7.

Author keywords:

Nitrogen heterocycles; Enamines; Cycloaddition; Azides; Reaction mechanisms ARYL AZIDES; ORGANIC AZIDES; REACTIVITY; ROUTE; 1,3-CYCLOADDITION; CYCLOADDITIONS; TRIAZOLINES; DERIVATIVES; CHEMISTRY; ENAMINES

DOI:

10.1002/ejoc.201402130

Web of Science ID:

ISI:000337693500023

Соавторы в МНС:

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Другие поля

Поле	Значение
Month	JUN
Publisher	WILEY-V C H VERLAG GMBH
Address	BOSCHSTRASSE 12, D-69469 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	ARYL AZIDES; ORGANIC AZIDES; REACTIVITY; ROUTE; 1,3-CYCLOADDITION; CYCLOADDITIONS; TRIAZOLINES; DERIVATIVES; CHEMISTRY; ENAMINES
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	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]; Russian Scientific Foundation; National Natural Science Foundation of China {[}21372132]; International Science \& Technology Cooperation Program of China {[}2014DFR41030]
Funding-Text	I. E. and V. B. thank the Russian Foundation for Basic Research (14-03-01033) and the Russian Scientific Foundation, and F. Z.-J. thanks the National Natural Science Foundation of China (21372132), and the International Science \& Technology Cooperation Program of China (2014DFR41030) for financial support.
Number-of-Cited-References	51
Usage-Count-Since-2013	27
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	AJ5AU