Synthesis of Multibromo-Substituted Quinolines by NBS-Mediated Cascade Electrophilic Bromination/Cyclization of N-(3-Phenylprop-2-ynyl)anilines

Abstract

A new and convenient protocol is presented here for the synthesis of 3,6,8-tribromoquinolines via cascade cyclization of N-(3-phenylprop-2-ynyl)anilines employing N-bromosuccinimide as an electrophile. The metal-free process is carried out under mild conditions and is compatible with a variety of substituents. The Sonogashira coupling reaction regioselectively occurs at position C-6 of the obtained products.

Key words

tribromoquinolines - electrophilic cyclization - N-bromosuccinimide - propargylanilines

Publication History

Received: 12 January 2021

Accepted after revision: 22 February 2021

Accepted Manuscript online:
22 February 2021

Article published online:
29 June 2021

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