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Synergistic I2/Amine Promoted Povarov-Type Reaction for the Synthesis of 2-Acyl-3-aryl(alkyl)quinolines Using Aryl(alkyl)acetaldehydes as Alkene Surrogates

Xiao Geng, Xia Wu, Peng Zhao, Jingjing Zhang, 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: chwuaxmail.ccnu.edu.cn

X. Geng, X. Wu, P. Zhao, J. Zhang, Y.-D. Wu, A.-X. Wu, Org. Lett., 2017, 19, 4179-4182.

DOI: 10.1021/acs.orglett.7b01686 (free Supporting Information)


Abstract

A synergistic I2/amine promoted formal [4 + 2] cycloaddition of methyl ketones, arylamines, and aryl(alkyl)acetaldehydes provides various 2-acyl-3-aryl(alkyl)quinolines via an iodination/Kornblum oxidation/Povarov/aromatization sequence. Notably, the arylamine reactants also acted as indispensable catalysts to promote enamine formation.


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proposed mechanism



I2-Promoted Povarov-Type Reaction Using 1,4-Dithane-2,5-diol as an Ethylene Surrogate: Formal [4 + 2] Synthesis of Quinolines

X. Wu, X. Geng, P. Zhao, J. Zhang, X. Gong, Y.-d. Wu, A.-x. Wu, Org. Lett., 2017, 19, 1550-1553.


Key Words

quinolines, multicomponent reactions, DMSO, iodine


ID: J54-Y2017