Electrophilic carbonyl activation: competing condensative cyclizations of tryptamine derivatives

TETRAHEDRON LETTERS

卷:56

Article

Liu, Fan¹  Movassaghi, Mohammad¹ 

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

关键词: Tryptamine;    Indole;    Cyclization;    Iminium ion;    Friedel-Crafts;   

DOI  :  10.1016/j.tetlet.2014.09.022

来源: Elsevier

【 摘 要 】

A series of tryptamine derived bisindole substrates were subjected to electrophilic activation of the functional grouping at their a-nitrogen in the form of iminium ions to enable cyclization onto the sterically hindered indole substructure. Our observations regarding divergent cyclization outcomes using electronically distinct bisindole substrates are described. Surprising preference for the Friedel Crafts alkylation reaction and evidence for an intriguing reversible spirocyclization are discussed. (C) 2014 Elsevier Ltd. All rights reserved.

【 授权许可】

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