通过胺介导的缺电子基团活化的2-亚甲基-1,3-二硫杂环戊烯的开环反应高效一锅法合成多官能化噻吩。

Efficient one-pot synthesis of polyfunctionalized thiophenes via an amine-mediated ring opening of EWG-activated 2-methylene-1,3-dithioles.

作者信息

Liang Fushun, Li Dazhi, Zhang Lei, Gao Jingjie, Liu Qun

机构信息

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

出版信息

Org Lett. 2007 Nov 8;9(23):4845-8. doi: 10.1021/ol7021752. Epub 2007 Oct 11.

DOI:10.1021/ol7021752

PMID:17929827

Abstract

An amine-mediated ring-opening reaction of EWG-activated 2-methylene-1,3-dithioles (EWG = electron-withdrawing group) was disclosed, and a new route to highly substituted thiophenes was developed via the ring opening of 1,3-dithioles and subsequent intramolecular annulation and amine substitution. This one-pot reaction could proceed efficiently under mild conditions.

摘要

公开了一种由胺介导的缺电子基团（EWG）活化的2-亚甲基-1,3-二硫杂环戊烯的开环反应，并通过1,3-二硫杂环戊烯的开环、随后的分子内环化和胺取代反应，开发了一条合成高度取代噻吩的新路线。该一锅法反应能在温和条件下高效进行。