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

A highly efficient molecular iodine mediated formal [3 + 2 + 1] cycloaddition reaction for the direct synthesis of substituted quinolines from methyl ketones, arylamines, and styrenes is developed. The methyl group of the methyl ketone represents uniquely reactive input in the Povarov reaction. A se...

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Bibliographic Details
Published in:Organic letters 2014-09, Vol.16 (17), p.4582-4585
Main Authors: Gao, Qinghe, Liu, Shan, Wu, Xia, Wu, Anxin
Format: Article
Language:English
Subjects:
Amines - chemistry
Catalysis
Cycloaddition Reaction
Iodine - chemistry
Ketones - chemistry
Molecular Structure
Quinolines - chemical synthesis
Quinolines - chemistry
Styrenes - chemistry
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Summary:A highly efficient molecular iodine mediated formal [3 + 2 + 1] cycloaddition reaction for the direct synthesis of substituted quinolines from methyl ketones, arylamines, and styrenes is developed. The methyl group of the methyl ketone represents uniquely reactive input in the Povarov reaction. A self-sequenced iodination/Kornblum oxidation/Povarov/aromatization mechanism has been proposed as a possible reaction sequence to account for the results observed in this study.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol502134u