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Copper-catalyzed tandem Ullmann type C–N coupling and dehydrative cyclization: synthesis of imidazo[1,2-c]quinazolines†
Nitesh K. Nandwana,Shiv Dhiman,Ganesh M. Shelke,Anil Kumar
Organic & Biomolecular Chemistry Pub Date : 12/22/2015 00:00:00 , DOI:10.1039/C5OB02469B
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
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