Literature DB >> 26120209

Electrophilic Carbonyl Activation: Competing Condensative Cyclizations of Tryptamine Derivatives.

Fan Liu1, Mohammad Movassaghi1.   

Abstract

A series of tryptamine derived bisindole substrates were subject to electrophilic activation of the functional grouping at their alpha-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 Friedel-Crafts alkylation reaction and evidence for an intriguing reversible spirocyclization are discussed.

Entities:  

Keywords:  Friedel-Crafts; cyclization; iminium ion; indole; tryptamine

Year:  2015        PMID： 26120209      PMCID： PMC4480791          DOI： 10.1016/j.tetlet.2014.09.022

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  31 in total

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