Three Sequential C-N Bond Formations: tert-Butyl Nitrite as a N1 Synthon in a Three Component Reaction Leading to Imidazo[1,2-a]quinolines and Imidazo[2,1-a]isoquinolines

Prasenjit Sau; Amitava Rakshit; Anju Modi; Ahalya Behera; Bhisma K Patel

doi:10.1021/acs.joc.7b02815

Three Sequential C-N Bond Formations: tert-Butyl Nitrite as a N1 Synthon in a Three Component Reaction Leading to Imidazo[1,2-a]quinolines and Imidazo[2,1-a]isoquinolines

J Org Chem. 2018 Jan 19;83(2):1056-1064. doi: 10.1021/acs.joc.7b02815. Epub 2018 Jan 8.

Authors

Prasenjit Sau¹, Amitava Rakshit¹, Anju Modi¹, Ahalya Behera¹, Bhisma K Patel¹

Affiliation

¹ Department of Chemistry, Indian Institute of Technology Guwahati , Guwahati 781039, India.

PMID: 29260562
DOI: 10.1021/acs.joc.7b02815

Abstract

tert-Butyl nitrite serves the dual role of an oxidant as well as a N1 synthon in a multicomponent reaction involving quinolines, isoquinolines, and styrenes. Herein, two sp² C-H functionalizations of styrenes and one sp² C-H functionalization of quinolines and isoquinolines lead to the formation of fused quinolines and isoquinolines via three sequential C-N bond formations.

Publication types

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