Sulfur-mediated synthesis of unsymmetrically substituted N-aryl oxalamides by the cascade thioamidation/cyclocondensation and hydrolysis reaction

Sulfur-mediated synthesis of unsymmetrically substituted N-aryl oxalamides by the cascade thioamidation/cyclocondensation and hydrolysis reaction Full article

Journal

Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539

Output data

Year: 2020, Volume: 18, Number: 26, Pages: 5050-5060 Pages count : 11 DOI: 10.1039/d0ob00811g

Authors

Tikhonova Tatyana A. ¹ , Ilment Nikita V. ¹ , Lyssenko Konstantin A. ^2,3 , Zavarzin Igor V. ¹ , Volkova Yulia A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., Moscow, Russian Federation
2	Department of Chemistry, M.V. Lomonosov Moscow State University, 119991 Moscow, Russian Federation
3	G.V. Plekhanov Russian University of Economics, 36 Stremyanny Per., Moscow 117997, Russian Federation

A facile and straightforward synthesis of unsymmetrically substituted N-aryl oxalamides from 2,2′-biphenyldiamines, 2-chloroacetic acid derivatives, elemental sulfur, and water has been developed. This protocol is distinguished by efficiency in water under metal-free conditions for N-aryl oxalamides bearing a side-chain NH2-group; it can be adapted for scale-up synthesis. The scope and limitations of this transformation have been investigated.

Tikhonova T.A. , Ilment N.V. , Lyssenko K.A. , Zavarzin I.V. , Volkova Y.A.
Sulfur-mediated synthesis of unsymmetrically substituted N-aryl oxalamides by the cascade thioamidation/cyclocondensation and hydrolysis reaction
Organic & Biomolecular Chemistry. 2020. V.18. N26. P.5050-5060. DOI: 10.1039/d0ob00811g WOS Scopus OpenAlex

≡ Web of science:	WOS:000546177200021
≡ Scopus:	2-s2.0-85088206789
≡ OpenAlex:	W3034829916