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Direct C-C Bond Cleavage of 1,3-Dicarbonyl Compounds as a Single-Carbon Synthon: Synthesis of 2-Aryl-4-quinolinecarboxylates

You Zhou, Peng Zhao, Li-Sheng Wang, Xiao-Xiao Yu, Chun Huang, Yan-Dong Wu and An-Xin Wu*

*Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China, Email:

Y. Zhou, P. Zhao, L.-S. Wang, X.-X. Yu, C. Huang, Y. D. Wu, A.-X. Wu, Org. Lett., 2021, 23, 6461-6465.

DOI: 10.1021/acs.orglett.1c02267


An efficient [2 + 1 + 3] cyclization reaction of aryl methyl ketones, arylamines, and 1,3-dicarbonyl compounds provides 2-aryl-4-quinolinecarboxylates in good yields under mild conditions. This metal-free process achieved a C-C bond cleavage of 1,3-dicarbonyl compounds for use as a C1 synthon.

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proposed mechanism

Key Words

Quinolines, Kornblum Oxidation, DMSO, Iodine, Multicomponent Reactions

ID: J54-Y2021