Sulfur-mediated synthesis of unsymmetrically substituted <i>N</i>-aryl oxalamides by the cascade thioamidation/cyclocondensation and hydrolysis reaction
Tatyana A. Tikhonova, Nikita V. Ilment, Konstantin А. Lyssenko, И. В. Заварзин, Yulia A. Volkova
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.
Topics & Concepts
ArylSulfurChemistryChloroacetic acidHydrolysisCascadeOrganic chemistryCascade reactionAcid hydrolysisMedicinal chemistryCatalysisAlkylChromatographySynthesis and Reactivity of Sulfur-Containing CompoundsSynthesis of heterocyclic compoundsSulfur-Based Synthesis Techniques