Microwave-assisted, solvent-free synthesis of 1-(α- or β-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinolines by the Mannich reaction

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Abstract

As a new extension of the Mannich reaction of naphthols, 1-(hydroxynaphthyl)-substituted 1,2,3,4-tetrahydroisoquinolines were synthesized by the nucleophilic addition of 1- or 2-naphthol to 3,4-dihydroisoquinolines under solvent-free conditions, using microwave irradiation. The additions to 3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline proved to be a highly diastereoselective processes, resulting in the cis isomers as the main or the only products.

Original languageEnglish
Pages (from-to)3881-3883
Number of pages3
JournalTetrahedron Letters
Volume47
Issue number23
DOIs
Publication statusPublished - Jun 5 2006

Fingerprint

Tetrahydroisoquinolines
Microwaves
Microwave irradiation
Isomers
1-naphthol
G 1616
2-naphthol

Keywords

  • 1-Naphthol
  • 2-Naphthol
  • Dihydroisoquinoline
  • Mannich reaction
  • Nucleophilic addition

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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abstract = "As a new extension of the Mannich reaction of naphthols, 1-(hydroxynaphthyl)-substituted 1,2,3,4-tetrahydroisoquinolines were synthesized by the nucleophilic addition of 1- or 2-naphthol to 3,4-dihydroisoquinolines under solvent-free conditions, using microwave irradiation. The additions to 3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline proved to be a highly diastereoselective processes, resulting in the cis isomers as the main or the only products.",
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author = "I. Szatm{\'a}ri and L. L{\'a}z{\'a}r and F. F{\"u}l{\"o}p",
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T1 - Microwave-assisted, solvent-free synthesis of 1-(α- or β-hydroxynaphthyl)-1,2,3,4-tetrahydroisoquinolines by the Mannich reaction

AU - Szatmári, I.

AU - Lázár, L.

AU - Fülöp, F.

PY - 2006/6/5

Y1 - 2006/6/5

N2 - As a new extension of the Mannich reaction of naphthols, 1-(hydroxynaphthyl)-substituted 1,2,3,4-tetrahydroisoquinolines were synthesized by the nucleophilic addition of 1- or 2-naphthol to 3,4-dihydroisoquinolines under solvent-free conditions, using microwave irradiation. The additions to 3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline proved to be a highly diastereoselective processes, resulting in the cis isomers as the main or the only products.

AB - As a new extension of the Mannich reaction of naphthols, 1-(hydroxynaphthyl)-substituted 1,2,3,4-tetrahydroisoquinolines were synthesized by the nucleophilic addition of 1- or 2-naphthol to 3,4-dihydroisoquinolines under solvent-free conditions, using microwave irradiation. The additions to 3-methyl-6,7-dimethoxy-3,4-dihydroisoquinoline proved to be a highly diastereoselective processes, resulting in the cis isomers as the main or the only products.

KW - 1-Naphthol

KW - 2-Naphthol

KW - Dihydroisoquinoline

KW - Mannich reaction

KW - Nucleophilic addition

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