One-pot α-arylation of β-carboline with indole and naphthol derivatives

Research output: Contribution to journalArticle

3 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)611-616
Number of pages6
JournalCurrent Organic Synthesis
Volume13
Issue number4
Publication statusPublished - Aug 1 2016

Fingerprint

Carbolines
Naphthols
Derivatives
Friedel-Crafts reaction
Nucleophiles
Microwave irradiation
Aromatic compounds
Microwaves
Skeleton
Electrons
Amino Acids
Catalysts
indole
1-naphthol

Keywords

  • Aza-Friedel-Crafts alkylation
  • Indole
  • Microwave reaction
  • Modified Mannich reaction
  • Naphthol
  • β-carboline

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

Cite this

One-pot α-arylation of β-carboline with indole and naphthol derivatives. / Sas, Judit; Szatmári, I.; Fülöp, F.

In: Current Organic Synthesis, Vol. 13, No. 4, 01.08.2016, p. 611-616.

Research output: Contribution to journalArticle

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AB - 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.

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