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One-pot α-arylation of β -carboline with Indole and Naphthol Derivatives

[ Vol. 13 , Issue. 4 ]

Author(s):

Judit Sas, István Szatmári and Ferenc Fulop   Pages 611 - 616 ( 6 )

Abstract:


4,9-Dihydro-3H- β-carboline and 6-methoxy-4,9-dihydro-3H- β -carboline were subjected to catalyst-free one-pot α -arylation with 1- or 2-naphthol, 6-hydroxyquinoline or 5-hydroxyisoquinoline as N-containing analogues via direct aza-Friedel-Crafts reactions. The procedure was then extended to other electron-rich aromatic compounds, such as indole or indole-2-carboxylic acid, to yield new indole γ-amino acid derivatives containing - β carboline skeleton. All the reactions were performed both under neat conditions and with microwave irradiation. The reaction of 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole and benzaldehyde with 1-naphthol as nucleophile led to the formation of the N-alkylated compound as a single product, whereas the reaction with 2-naphtol resulted in the two possible α-arylated/N-alkylated products, in a ratio depending on the reaction conditions.

Keywords:

β-Carboline, Indole, Naphthol, Aza-Friedel-Crafts alkylation, modified Mannich reaction, Microwave reaction.

Affiliation:

Institute of Pharmaceutical Chemistry and Research Group for Stereochemistry, Hungarian Academy of Sciences, University of Szeged, H-6720 Szeged, Eötvös u. 6, Hungary.

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