One-Pot Three-Component Synthesis of Pyrrolidin-2-ones via a Sequential Wittig/Nucleophilic Addition/Cyclization Reaction

Zhi-Rong Guan; Shuai Liu; Zi-Ming Liu; Ming-Wu Ding

doi:10.1055/s-0037-1612279

Synthesis, Table of Contents

Synthesis 2019; 51(11): 2402-2408
DOI: 10.1055/s-0037-1612279

paper

One-Pot Three-Component Synthesis of Pyrrolidin-2-ones via a Sequential Wittig/Nucleophilic Addition/Cyclization Reaction

Zhi-Rong Guan ‡

,

Shuai Liu ‡

,

Zi-Ming Liu

,

Ming-Wu Ding *

Key Laboratory of Pesticide & Chemical Biology of Ministry of Education, Hubei International Scientific and Technological Cooperation Base of Pesticide and Green Synthesis, Central China Normal University, Wuhan 430079, P. R. of China Email: mwding@mail.ccnu.edu.cn

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Abstract

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‡ These authors contributed equally to this work.

Abstract

A new efficient synthesis of pyrrolidin-2-ones via sequential Wittig reaction/nucleophilic addition/cyclization was developed. The Wittig reaction of the phosphoranes with isocyanates produced ketenimine intermediates that were then treated with primary amines to give amidines, which were treated with catalytic sodium alkoxide to give 2-imino-5-oxopyrrolidine-3-carboxylates in good yields.

Key words

pyrrolidin-2-one - Wittig reaction - ketenimine - amidine - isocyanate

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References

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