Synthesis of 6-Substituted Pyrido[2,3- b ]indoles by Electrophilic Substitution

Cédric Schneider (1) , David Gueyrard (2) , Florence Popowycz (3) , Benoît Joseph (4) , Peter Goekjian (5)

1 COBRA - Chimie Organique et Bioorganique : Réactivité et Analyse
2 ISCR - Institut des Sciences Chimiques de Rennes
3 ICBMS - Institut de Chimie et Biochimie Moléculaires et Supramoléculaires
4 ICOA - Institut de Chimie Organique et Analytique
5 CO2GLYCO - Chimie Organique 2-Glycochimie

Regioselective electrophilic aromatic substitutions, acylation, bromination, and formylation, of unprotected pyrido[2,3-b]indole (α-carbolines) at the C-6 position are described. Alter­native conditions for the nitration were investigated, which led to the ­unexpected appearance of the minor C-8 isomer.

Keywords: heterocycles; acylations; halogenation; regioselectivity; electrophilic aromatic substitutions; azacarbazole

Domains: Chemical Sciences; Chemical Sciences; Organic chemistry; Chemical Sciences; Catalysis

Cédric Schneider, David Gueyrard, Florence Popowycz, Benoît Joseph, Peter Goekjian. Synthesis of 6-Substituted Pyrido[2,3- b ]indoles by Electrophilic Substitution. SYNLETT, 2007, 2007 (14), pp.2237-2241. ⟨10.1055/s-2007-985566⟩. ⟨hal-02380611⟩