Copper-Catalyzed Multicomponent Domino Reaction of 2-Bromobenzaldehydes, Aryl Methyl Ketones, and Sodium Azide: Access to 1 H-[1,2,3]Triazolo[4,5- c]quinoline Derivatives

J Org Chem. 2018 Dec 7;83(23):14802-14810. doi: 10.1021/acs.joc.8b02476. Epub 2018 Nov 28.

Abstract

A practical copper-catalyzed multicomponent reaction has been developed for the synthesis of 1 H-[1,2,3]triazolo[4,5- c]quinoline derivatives from commercially available 2-bromobenzaldehydes, aryl methyl ketones, and sodium azide. This protocol integrated consecutive base-promoted condensation, [3 + 2] cycloaddition, copper-catalyzed SNAr, and denitrogenation cyclization sequences. Preliminary mechanistic studies revealed that CuBr2 acted as a multifunctional catalyst to streamline this domino process. The mild catalytic system enabled effective construction of one C-C and four C-N bonds in one operation.

Publication types

  • Research Support, Non-U.S. Gov't