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Sulfur-mediated synthesis of unsymmetrically substituted N-aryl oxalamides by the cascade thioamidation/cyclocondensation and hydrolysis reaction†
Tatyana A. Tikhonova,Nikita V. Ilment,Igor V. Zavarzin,Yulia A. Volkova
Organic & Biomolecular Chemistry Pub Date : 06/16/2020 00:00:00 , DOI:10.1039/D0OB00811G
Abstract

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.

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