Selective N-alkylation of isoquinolines, benzazepines and thienopyridines with aromatic aldehydes and naphthols Dedicated to the memory of Professor A. R. Katritzky

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6 Citations (Scopus)

Abstract

Abstract The reactions of 1- or 2-naphthol, benzaldehyde or substituted benzaldehydes with tetrahydroisoquinoline, tetrahydrobenzo[d]azepine, tetrahydrobenzo[c]azepine or tetrahydrothieno[3,2-c]pyridine under solvent-free conditions, allowed a series of tertiary aminonaphthols to be prepared. The reactions were accelerated by the use of microwave irradiation, and the yields were also improved. As an exception, the aminoalkylation of 2-naphthol with 1,2,3,4-tetrahydroisoquinoline in the presence of benzaldehyde led to the parallel N-alkylation and redox α-arylation of the tetrahydroisoquinoline in a ratio of 4:1. The reaction of 1-naphthol with 2,3,4,5-tetrahydro-1H-benzo[c]azepine led to the formation of the N-alkylated compound as a single product, illustrating that the reaction route depends on the structures of the cyclic amine and the naphthol.

Original languageEnglish
Article number26493
Pages (from-to)7216-7221
Number of pages6
JournalTetrahedron
Volume71
Issue number39
DOIs
Publication statusPublished - Aug 17 2015

Keywords

  • Aminonaphthol
  • Mannich reaction
  • N-alkylation
  • Tetrahydroisoquinoline
  • α-Functionalization

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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