A facile and efficient synthesis of polyfunctionalized pyridin-2(1H)-ones from beta-oxo amides under Vilsmeier conditions

Dexuan Xiang; Kewei Wang; Yongjiu Liang; Guangyuan Zhou; Dewen Dong

doi:10.1021/ol702846t

A facile and efficient synthesis of polyfunctionalized pyridin-2(1H)-ones from beta-oxo amides under Vilsmeier conditions

Org Lett. 2008 Jan 17;10(2):345-8. doi: 10.1021/ol702846t. Epub 2007 Dec 28.

Authors

Dexuan Xiang¹, Kewei Wang, Yongjiu Liang, Guangyuan Zhou, Dewen Dong

Affiliation

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

PMID: 18161982
DOI: 10.1021/ol702846t

Abstract

A facile and efficient one-pot synthesis of polysubstituted pyridin-2(1H)-ones from a variety of beta-oxo amides under Vilsmeier conditions is described, and a mechanism involving sequential halogenation, formylation and intramolecular nucleophilic cyclization is proposed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amides / chemistry*
Catalysis
Molecular Structure
Pyridones / chemical synthesis*
Pyridones / chemistry
Stereoisomerism

Substances

Amides
Pyridones