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Radical cation salt induced tandem cyclization between anilines and N-vinyl amides: synthesis of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinoline derivatives

✍ Scribed by Xiao-dong Jia; Yan Ren; Cong-de Huo; Wen-Juan Wang; Xiang-Ning Chen; Xiao-Lan Xu; Xi-cun Wang

Publisher
Elsevier Science
Year
2010
Tongue
French
Weight
379 KB
Volume
51
Category
Article
ISSN
0040-4039

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✦ Synopsis

A tandem cyclization of imines with N-vinyllactams induced by TBPA +Γ… was investigated, and a series of 2-methyl-4-anilino-1,2,3,4-tetrahydroquinolines were synthesized based on a domino process in which N-vinyllactams serve as an acetaldehyde surrogate. A single electron transfer mechanism was proposed and radical cation salt acts as both a Lewis acid and one electron oxidant to induce such transformation.

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