Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl2 and dimethyl/diethyl sulfoxides

Jingran Zhang; Beibei Zhang; Jiaxin He; Haofeng Shi; Yunfei Du

doi:10.1039/d2ob01580c

Divergent synthesis of 2-methylthioindole and 2-unsubstituted indole derivatives mediated by SOCl₂ and dimethyl/diethyl sulfoxides

Org Biomol Chem. 2022 Oct 19;20(40):7886-7890. doi: 10.1039/d2ob01580c.

Authors

Jingran Zhang¹, Beibei Zhang¹, Jiaxin He¹, Haofeng Shi¹, Yunfei Du¹

Affiliation

¹ School of Pharmaceutical Science and Technology, Tianjin University, Tianjin 300072, China. duyunfeier@tju.edu.cn.

PMID: 36169012
DOI: 10.1039/d2ob01580c

Abstract

A metal-free divergent synthesis of indole compounds dependent on a reagent via intramolecular C(sp²)-H amination was described. The reaction of 2-vinylanilines with DMSO/SOCl₂ at 70 °C was found to give 2-thiomethylindoles, while replacing DMSO with diethyl sulfoxide afforded 2-unsubstituted indoles in a highly selective manner.

Publication types

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

MeSH terms

Amination
Dimethyl Sulfoxide*
Indoles
Sulfoxides*

Substances

Dimethyl Sulfoxide
diethyl sulfoxide
Sulfoxides
Indoles