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

Xia Wu, Xiao Geng, Peng Zhao, Jingjing Zhang, Xingxing Gong, 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, China, Email: chwuydmail.ccnu.edu.cn, chwuaxmail.ccnu.edu.cn

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

DOI: 10.1021/acs.orglett.7b00361 (free Supporting Information)


Abstract

A highly efficient I2-promoted formal [4 + 2] cycloaddition enables the synthesis of 2-acylquinolines from methyl ketones and arylamines using 1,4-dithane-2,5-diol as an ethylene surrogate. This reaction occurred via an iodination/Kornblum oxidation/Povarov/aromatization sequence with an important role of the arylamine substrate in promoting the reaction.

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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

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


Key Words

quinolines, DMSO, I2


ID: J54-Y2017