New Facile Synthesis of Imidazo[2,1-b]-1,3,4-thiadiazol-5(6H)-ones via aza-Wittig Reaction

Ming-Wu Ding; Bo-Qiao Fu; Lin Cheng

doi:10.1055/s-2004-822333

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New Facile Synthesis of Imidazo[2,1-b]-1,3,4-thiadiazol-5(6H)-ones via aza-Wittig Reaction

Ming-Wu Ding*, Bo-Qiao Fu, Lin Cheng
Institute of Organic Synthesis, Central China Normal University, Wuhan, 430079, P. R. China
Fax: +86(27)67867959; e-Mail: ding5229@yahoo.com.cn;

Abstract

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Abstract

The isothiocyanates 2, obtained from aza-Wittig reactions of vinyliminophosphoranes 1 with CS₂, reacted with hydrazine to give 3-amino-2-thioxo-4-imidazolidinones 4. Reactions of 4 with triphenyphosphine, hexachloroethane and Et₃N produced iminophosphoranes 5. A tandem aza-Wittig reaction of iminophosphoranes 5 with isocyanates generated imidazo[2,1-b]-1,3,4-thiadiazol-5(6H)-ones 7 in moderate yield.

Key words

imidazo[2,1-b]-1,3,4-thiadiazol-5(6H)-one - iminophosphorane - carbodiimide - aza-Wittig reaction - synthesis

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References

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