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<p>A one-pot reaction of arylamines with carbon disulfide and <i>N</i>-arylmaleimides at different ratios of reagents gave two types of substituted thiazolones: <i>N</i>-aryl-2-(3-aryl-4-oxo-2-thioxothiazolidin-5-yl)acetamides and <i>N</i>-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 <i>N</i>-aryldithiocarbamic acids, and treatment of the latter with <i>N</i>-arylmaleimides resulted in <i>N</i>-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 <i>N</i><sup>1</sup>,<i>N</i><sup>2</sup>-diarylthioureas, and treatment of the latter with <i>N</i>-arylmaleimides resulted in <i>N</i>-aryl-2-(3-aryl-2-arylimino-4-oxothiazolidin-5-yl)acetamides. A three-component mode at different ratios of <i>N</i>-arylmaleimide, arylamine, and carbon disulfide gave <i>N</i>-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]-<i>N</i>-(4-chlorophenyl)acetamide efficiently suppresses the replication of the SARS-CoV-2 virus.</p>

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

  • 期刊论文

  • 发表日期：

    2025年4月1日

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  • A. A. Belokon,
  • N. V. Stolpovskaya,
  • A. V. Zorina,
  • O. V. Pyankov,
  • M. A. Prezent,
  • M. E. Minyaev,
  • Kh. S. Shikhaliev

摘要

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.