PubAg

Main content area

Visible light induced regioselective C5 halogenation of 8-aminoquinolines with 1,3-dihalo-5,5-dimethylhydantoin in continuous flow

Author:
Shu, Quan, Li, Yaming, Liu, Tong, Zhang, Siyu, Jiang, Linlin, Jin, Kun, Zhang, Rong, Duan, Chunying
Source:
Tetrahedron 2019 v.75 no.26 pp. 3636-3642
ISSN:
0040-4020
Subject:
air, ambient temperature, aminoquinolines, chemical reactions, light, moieties, regioselectivity
Abstract:
An efficient and convenient method for remote C5 halogenation of 8-aminoquinoline derivatives was developed in continuous flow at room temperature. This method employed inexpensive 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichlro-5,5-dimethylhydantoin (DCDMH) as halogenation reagents and visible light to catalyze the reaction. The reaction is scalable to gram-scale and proceeded with air and moisture tolerance, good functional group compatibility, and outstanding site selectivity, providing a new pathway for C5 halogenation of 8-aminoquinolines.
Agid:
6448715