Issue 5, 2016

Copper-catalyzed tandem Ullmann type C–N coupling and dehydrative cyclization: synthesis of imidazo[1,2-c]quinazolines

Abstract

A simple and efficient one-pot protocol has been demonstrated for the synthesis of imidazo[1,2-c]quinazoline derivatives through a copper catalyzed tandem reaction between substituted 2-(2-bromophenyl)-1H-imidazoles and formamide. The synthetic protocol involves initial Ullmann-type C–N coupling followed by intramolecular dehydrative cyclization. The method uses readily available 2-(2-bromophenyl)-1H-imidazoles as the starting materials to afford imidazo[1,2-c]quinazolines in moderate to good yields and provided 610 mg (71%) yield of 3a from a gram scale reaction.

Graphical abstract: Copper-catalyzed tandem Ullmann type C–N coupling and dehydrative cyclization: synthesis of imidazo[1,2-c]quinazolines

Supplementary files

Article information

Article type
Paper
Submitted
02 Dec 2015
Accepted
22 Dec 2015
First published
22 Dec 2015

Org. Biomol. Chem., 2016,14, 1736-1741

Author version available

Copper-catalyzed tandem Ullmann type C–N coupling and dehydrative cyclization: synthesis of imidazo[1,2-c]quinazolines

N. K. Nandwana, S. Dhiman, G. M. Shelke and A. Kumar, Org. Biomol. Chem., 2016, 14, 1736 DOI: 10.1039/C5OB02469B

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