4.5 Article

Synthesis of 2-, 3-, and 4-Substituted Pyrido[2,3-b]indoles by C-N, C-O, and C-C(sp) Bond Formation

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2010, Issue 34, Pages 6665-6677

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201000795

Keywords

Natural products; Nitrogen heterocycles; Palladium; Polycycles; Cross-coupling

Funding

  1. French Ministere de l'Enseignement Superieur et de la Recherche (MESR)
  2. European Union [LSHB-CT-2004-503467]

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The synthesis of 2-, 3-, and 4-substituted alpha-carbolines is described starting from the corresponding chloropyrido[2,3-b]-indoles by Buchwald-Hartwig and Sonogashira cross-coupling reactions. Regioselective Sonogashira reactions on 2,4-dichloropyrido[2,3-b]indoles are also presented as an efficient route to unsymmetrically 2,4-disubstituted alpha-carbolines.

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