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Povarov-Type Reaction Using Methyl as New Input: Direct Synthesis of Substituted Quinolines by I2-Mediated Formal [3 + 2 + 1] Cycloaddition

Qinghe Gao, Shan Liu, Xia Wu and Anxin 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

Q. Gao, S. Liu, X. Wu, A. Wu, Org. Lett., 2014, 16, 4582-4585.

DOI: 10.1021/ol502134u (free Supporting Information)


Abstract

A highly efficient molecular iodine mediated formal [3 + 2 + 1] cycloaddition reaction enables the direct synthesis of substituted quinolines from methyl ketones, arylamines, and styrenes. A self-sequenced iodination/Kornblum oxidation/Povarov/aromatization mechanism has been proposed.


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Key Words

quinolines, multicomponent reactions, iodine


ID: J54-Y2014