Efficient synthesis of highly substituted Pyrrolin-4-ones via PIFA-mediated cyclization reactions of enaminones

Jie Huang; Yongjiu Liang; Wei Pan; Yang Yang; Dewen Dong

doi:10.1021/ol702362n

Efficient synthesis of highly substituted Pyrrolin-4-ones via PIFA-mediated cyclization reactions of enaminones

Org Lett. 2007 Dec 20;9(26):5345-8. doi: 10.1021/ol702362n. Epub 2007 Nov 30.

Authors

Jie Huang¹, Yongjiu Liang, Wei Pan, Yang Yang, Dewen Dong

Affiliation

¹ Department of Chemistry, Northeast Normal University, Changchun 130024, China.

PMID: 18047359
DOI: 10.1021/ol702362n

Abstract

A convenient and efficient synthesis of highly substituted pyrrolin-4-ones is developed via the PIFA-mediated cyclization reactions of readily available enaminones, and a mechanism involving sequential cleavage of N-C bond, formation of new N-C bond, intramolecular addition reaction, and benzilic acid type rearrangement is proposed.