Reactions of β-azolylenamines with sulfonyl azides as an approach to N-unsubstituted 1,2,3-triazoles and ethene-1,2-diamines / Efimov I., Bakulev V., Beliaev N., Beryozkina T., Knippschild U., Leban J., Zhi-Jin F., Eltsov O., Slepukhin P., Ezhikova M., Dehaen W. // European Journal of Organic Chemistry. - 2014. - V. 2014, l. 17. - P. 3684-3689.

ISSN:

1434193X

Type:

Article

Abstract:

The reactions of β-azolylenamines 1 with sulfonyl azides 2 in acetonitrile furnished 1H-4-(azol-5-yl)-1,2,3-triazoles 3 in yields of 52-93%. β-Benzoylenaminones and β-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. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Author keywords:

Azides; Cycloaddition; Enamines; Nitrogen heterocycles; Reaction mechanisms

Index keywords:

нет данных

DOI:

10.1002/ejoc.201402130

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https://www.scopus.com/inward/record.uri?eid=2-s2.0-84901813865&doi=10.1002%2fejoc.201402130&partnerID=40&md5=32b363e88c73ffda79df112da11de592

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Affiliations	TOS Laboratory of Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 Mira st., 620002 Ekaterinburg, Russian Federation; Klinik für Allgemein- und Viszeralchirurgie, Zentrum für Chirurgie, Universitätsklinikum Ulm, 23 Albert-Einstein-Allee, 89081 Ulm, Germany; Gert Lubec Proteomics Laboratory, Medicinal University of Vienna, 14 Lazarettgasse, 1090 Vienna, Austria; State Key Laboratory of Elemento-Organic Chemistry, Nankai University, 300071 Tianjin, China; I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Science, 20 S. Kovalevskaya st., 620990 Ekaterinburg, Russian Federation; Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium
Author Keywords	Azides; Cycloaddition; Enamines; Nitrogen heterocycles; Reaction mechanisms
Funding Details	14-03-01033, RFBR, Russian Foundation for Basic Research; 21372132, NSFC, Russian Foundation for Basic Research
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Correspondence Address	Bakulev, V.; TOS Laboratory of Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 Mira st., 620002 Ekaterinburg, Russian Federation; email: v.a.bakulev@urfu.ru
Publisher	Wiley-VCH Verlag
CODEN	EJOCF
Language of Original Document	English
Abbreviated Source Title	Eur. J. Org. Chem.
Source	Scopus