Reactions of Thioacetamide Derivatives with Sulfonyl Azides: An Approach to Active-Methylene N-Sulfonylacetamidines / Dianova L., Berseneva V., Beryozkina T., Efimov I., Kosterina M., Eltsov O., Dehaen W., Bakulev V. // European Journal of Organic Chemistry. - 2015. - V. 2015, l. 31. - P. 6917-6923.

ISSN:

1434193X

Type:

Article

Abstract:

Reactions of functionalized [CN, CO2Et, C(O)NHR, C(S)NR1R2] derivatives of thiomalonic acid and 2-arylthioacetamides with sulfonyl azides were shown to give active-methylene N-sulfonylamidines in 62-98 yields. Various procedures for the reactions, including the use of pyridine, boiling ethanol, and water, or running the reactions in the absence of a base and solvent at 80 C, were carried out and compared. The solvent-free variant was the best in terms of yield, and also because it does not require the use of an excess of the toxic and hazardous azides. The reaction was shown to tolerate electron-withdrawing substituents such as carbonyl, cyano, and aryl groups at the C-2 position. The presence of alkyl and phenyl groups on the nitrogen atom of the thioacetamide fragment, and the presence of substituents on the sulfonyl group were also tolerated. Thus, an efficient solvent-free, catalyst-free, and base-free synthetic approach for the synthesis of N-sulfonylmalonacetamidines and 2-arylacetamidines was found. An efficient, solvent-free and base-free approach to active-methylene N-sulfonylacetamidines has been developed. © 2015 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Author keywords:

Azides; Sulfonamides; Synthetic methods; Thioamides

Index keywords:

нет данных

DOI:

10.1002/ejoc.201500968

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https://www.scopus.com/inward/record.uri?eid=2-s2.0-84944789961&doi=10.1002%2fejoc.201500968&partnerID=40&md5=27dded525442702e6a386a9920902a76

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Link	https://www.scopus.com/inward/record.uri?eid=2-s2.0-84944789961&doi=10.1002%2fejoc.201500968&partnerID=40&md5=27dded525442702e6a386a9920902a76
Affiliations	TOSLab of Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 Mira st., Yekaterinburg, Russian Federation; Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Celestijnenlaan 200F, Leuven, Belgium
Author Keywords	Azides; Sulfonamides; Synthetic methods; Thioamides
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Correspondence Address	Bakulev, V.; TOSLab of Ural Federal University Named after the First President of Russia B. N. Yeltsin, 19 Mira st., Russian Federation
Publisher	Wiley-VCH Verlag
CODEN	EJOCF
Language of Original Document	English
Abbreviated Source Title	Eur. J. Org. Chem.
Source	Scopus