Facile Synthesis of 4-Arylidene-1H-imidazol-5(4H)-ones by an Ugi–Aza-Wittig Sequence

Ying Wang; Hai Xie; Yu-Rong Pan; Ming-Wu Ding

doi:10.1055/s-0033-1338566

Synthesis, Table of Contents

Synthesis 2014; 46(03): 336-342
DOI: 10.1055/s-0033-1338566

paper

Facile Synthesis of 4-Arylidene-1H-imidazol-5(4H)-ones by an Ugi–Aza-Wittig Sequence

Authors

Ying Wang

^aKey Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China Fax: +86(27)67862041 Email: mwding@mail.ccnu.edu.cn
Hai Xie

^bCollege of Chemistry & Chemical Engineering, Shanxi Datong University, Shanxi 037009, P. R. of China
Yu-Rong Pan

^aKey Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China Fax: +86(27)67862041 Email: mwding@mail.ccnu.edu.cn
Ming-Wu Ding*

^aKey Laboratory of Pesticide & Chemical Biology of Ministry of Education, Central China Normal University, Wuhan 430079, P. R. of China Fax: +86(27)67862041 Email: mwding@mail.ccnu.edu.cn

Abstract

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Abstract

Vinyl azides, obtained from the Ugi-type reaction of 2-azido-3-arylacrylic acid, secondary amine, aldehyde, and isocyanide, react with triphenylphosphine to give a variety of 4-arylidene-1H-imidazol-5(4H)-ones in high yields via sequential Staudinger and intramolecular aza-Wittig reaction.

Key words

1H-imidazol-5(4H)-ones - Ugi reaction - aza-Wittig reaction - iminophosphoranes - azides

Full Text

References

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Supplementary Material

Supporting Information (PDF)