通过1-乙酰基-1-氨基甲酰基环丙烷的Vilsmeier-Haack反应高效一锅法合成高度取代的吡啶-2(1H)-酮

Efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones via the Vilsmeier-Haack reaction of 1-acetyl,1-carbamoyl cyclopropanes.

作者信息

Pan Wei, Dong Dewen, Wang Kewei, Zhang Jie, Wu Rigenhada, Xiang Dexuan, Liu Qun

机构信息

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

出版信息

Org Lett. 2007 Jun 7;9(12):2421-3. doi: 10.1021/ol070905i. Epub 2007 May 16.

DOI:10.1021/ol070905i

PMID:17503843

Abstract

A facile and efficient one-pot synthesis of highly substituted pyridin-2(1H)-ones is developed via the Vilsmeier-Haack reaction of readily available 1-acetyl,1-carbamoyl cyclopropanes, and a mechanism involving sequential ring-opening, haloformylation, and intramolecular nucleophilic cyclization reactions is proposed.

摘要

通过易得的1-乙酰基-1-氨基甲酰基环丙烷的Vilsmeier-Haack反应，开发了一种简便高效的一锅法合成高取代吡啶-2(1H)-酮的方法，并提出了一种涉及顺序开环、卤仿甲酰化和分子内亲核环化反应的机理。