Synthesis 2019; 51(11): 2402-2408
DOI: 10.1055/s-0037-1612279
paper
© Georg Thieme Verlag Stuttgart · New York

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
,
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
› Author Affiliations
We gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (No. 21572075) and the 111 Project B17019.
Further Information

Publication History

Received: 06 November 2018

Accepted after revision: 28 January 2019

Publication Date:
04 March 2019 (online)


‡ 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.

Supporting Information