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

Cédric Schneider (1) , David Goyard (2) , David Gueyrard (2) , Benoît Joseph (3) , Peter Goekjian (2)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
3 ICOA - Institut de Chimie Organique et Analytique

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.

Domaines: Catalyse; Chimie organique; Chimie

Cédric Schneider, David Goyard, David Gueyrard, Benoît Joseph, Peter Goekjian. Synthesis of 2-, 3-, and 4-Substituted Pyrido[2,3-b]indoles by C-N, C-O, and C-C(sp) Bond Formation. European Journal of Organic Chemistry, 2010, 2010 (34), pp.6665-6677. ⟨10.1002/ejoc.201000795⟩. ⟨hal-02351724⟩