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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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

Fingerprint

Isoquinolines
Thienopyridines
Azepines
Benzazepines
Naphthols
Alkylation
Aldehydes
Tetrahydroisoquinolines
Data storage equipment
Benzaldehydes
Microwave irradiation
Microwaves
Oxidation-Reduction
Amines
2-naphthol
1-naphthol
benzaldehyde

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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title = "Selective N-alkylation of isoquinolines, benzazepines and thienopyridines with aromatic aldehydes and naphthols Dedicated to the memory of Professor A. R. Katritzky",
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.",
keywords = "Aminonaphthol, Mannich reaction, N-alkylation, Tetrahydroisoquinoline, α-Functionalization",
author = "Judit Sas and I. Szatm{\'a}ri and F. F{\"u}l{\"o}p",
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T1 - Selective N-alkylation of isoquinolines, benzazepines and thienopyridines with aromatic aldehydes and naphthols Dedicated to the memory of Professor A. R. Katritzky

AU - Sas, Judit

AU - Szatmári, I.

AU - Fülöp, F.

PY - 2015/8/17

Y1 - 2015/8/17

N2 - 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.

AB - 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.

KW - Aminonaphthol

KW - Mannich reaction

KW - N-alkylation

KW - Tetrahydroisoquinoline

KW - α-Functionalization

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