Journal of Organic Chemistry p. 14802 - 14810 (2018)
Update date:2022-08-03
Topics:
Xu, Cheng
Jiang, Shi-Fen
Wu, Yan-Dong
Jia, Feng-Cheng
Wu, An-Xin
A practical copper-catalyzed multicomponent reaction has been developed for the synthesis of 1H-[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.
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