Reactions of Thioacetamide Derivatives with Sulfonyl Azides: An Approach to Active-Methylene N-Sulfonylacetamidines / Dianova Lidia,Berseneva Vera,Beryozkina Tetyana,Efimov Ilya,Kosterina Maria,Eltsov Oleg,Dehaen Wim,Bakulev Vasiliy // EUROPEAN JOURNAL OF ORGANIC CHEMISTRY. - 2015. - V. , l. 31. - P. 6917-6923.

ISSN/EISSN:

1434-193X / 1099-0690

Type:

Article

Abstract:

Reactions of functionalized {[}CN, CO2Et, C(O)NHR, C(S)(NRR2)-R-1] 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 degrees 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.

Author keywords:

Synthetic methods; Azides; Sulfonamides; Thioamides ARYL AZIDES; THIOAMIDES; 1,2,3-TRIAZOLES; REARRANGEMENTS; HETEROCYCLES; ACCESS; ALKYL

DOI:

10.1002/ejoc.201500968

Web of Science ID:

ISI:000363485200015

Соавторы в МНС:

Другие поля

Поле	Значение
Month	OCT
Publisher	WILEY-V C H VERLAG GMBH
Address	POSTFACH 101161, 69451 WEINHEIM, GERMANY
Language	English
EISSN	1099-0690
Keywords-Plus	ARYL AZIDES; THIOAMIDES; 1,2,3-TRIAZOLES; REARRANGEMENTS; HETEROCYCLES; ACCESS; ALKYL
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 Scientific Foundation {[}15-13-10031]
Funding-Text	This project was supported by the Russian Scientific Foundation (15-13-10031).
Number-of-Cited-References	31
Usage-Count-Last-180-days	1
Usage-Count-Since-2013	13
Journal-ISO	Eur. J. Org. Chem.
Doc-Delivery-Number	CU4GJ