The Synthesis of 2-Alkylthio-3-alkyl-5-arylmethylidene4H-imidazol-4-ones

Abstract

2-alkylthio-3-alkyl-5-arylmethylidene-4H-imidazol-4-ones were synthesized by the S-alkylation and N-alkylation of 2-thioxo-5-arylmethylidene-4-imidazolidinones, which were obtained via a tandem aza-Wittig reaction of vinyliminophosphoranes, carbon disulfide, and excess ammonium hydroxide (28% NH₃ in water).

Keywords:

• 4H-imidazol-4-ones
• alkylation
• aza-Wittig reaction
• synthesis

Acknowledgments

We gratefully acknowledge the financial support of this work by the Natural Science Foundation of Hubei Education Commission of China (Project No. D200560003) and the National Natural Science Foundation of China (Project No. 20102001).

Notes

^a Isolated yields of 4 based on vinyliminophosphoranes 1.

^b Purified yields of 5 based on 2-thioxo-5-arylmethylidene-4-imidazolidinones 4.