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Radical Cyclization of 2-Alkenylthioanilides: A Novel Synthesis of 2,3-Disubstituted Indoles

Radical Cyclization of 2-Alkenylthioanilides: A Novel Synthesis of 2,3-Disubstituted Indoles

  1. trptamene
    This is the "2nd generation" of the other article I added (JACS, 116, 3127 (1994))



    The indole nucleus is present in a wide range of natural
    products, and the synthesis of this important structure has been a
    steady topic of interest for many years.1 Among the numerous
    methods that have been developed for the synthesis of indoles,
    few practical and mild procedures are available for the construction
    of 2,3-disubstituted indoles.2 Specifically, although the
    venerable Fischer indole synthesis still sees frequent use, the
    general necessity for acid and heat often produces significant
    purification difficulties.3 Furthermore, the more recently developed
    Gassman and Fu¨rstner indole syntheses require the frequently
    laborious synthesis of R-thiomethyl ketones and o,N-diacylanilines,
    respectively.4,5 In this communication, we describe a
    novel indole synthesis that is carried out under mild radical
    cyclization conditions. In addition, we show that the thioanilide
    indole precursors may be easily synthesized in a modular fashion,
    to make accessible a wide range of 2,3-disubstituted indoles, in
    some cases with substituents on the carbocyclic aromatic ring as
    well.
    In an