One-pot synthesis of new thiazole derivatives via the reaction of arylamines, carbon disulfide, and N-arylmaleimides and evaluations of their antiviral activity

Abstract

A one-pot reaction of arylamines with carbon disulfide and N-arylmaleimides at different ratios of reagents gave two types of substituted thiazolones: N-aryl-2-(3-aryl-4-oxo-2-thioxothiazolidin-5-yl)acetamides and N-aryl-2-(3-aryl-2-arylimino-4-oxothiazolidin-5-yl)acetamides. The reaction of arylamine with a small excess of carbon disulfide in acetonitrile led to N-aryldithiocarbamic acids, and treatment of the latter with N-arylmaleimides resulted in N-aryl-2-(3-aryl-4-oxo-2-thioxothiazolidin-5-yl)acetamides. The reaction of a twofold excess of arylamine with carbon disulfide in acetonitrile led to N¹,N²-diarylthioureas, and treatment of the latter with N-arylmaleimides resulted in N-aryl-2-(3-aryl-2-arylimino-4-oxothiazolidin-5-yl)acetamides. A three-component mode at different ratios of N-arylmaleimide, arylamine, and carbon disulfide gave N-aryl-2-(3-aryl-4-oxo-2-thioxothiazolidin-5-yl)acetamides as the major reaction product. Evaluations of the antiviral activity of synthesized derivatives revealed that 2-[3-(4-methoxyphenyl)-4-oxo-2-thioxothiazolidin-5-yl]-N-(4-chlorophenyl)acetamide efficiently suppresses the replication of the SARS-CoV-2 virus.