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Issue 26, 2020
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Sulfur-mediated synthesis of unsymmetrically substituted N-aryl oxalamides by the cascade thioamidation/cyclocondensation and hydrolysis reaction

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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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Article information


Submitted
19 Apr 2020
Accepted
16 Jun 2020
First published
16 Jun 2020

Org. Biomol. Chem., 2020,18, 5050-5060
Article type
Paper

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

T. A. Tikhonova, N. V. Ilment, K. A. Lyssenko, I. V. Zavarzin and Y. A. Volkova, Org. Biomol. Chem., 2020, 18, 5050
DOI: 10.1039/D0OB00811G

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