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Synthesis of 8-Fluoro-3,4-dihydroisoquinoline and Its Transformation to 1,8-Disubstituted Tetrahydroisoquinolines.

A simple procedure for the synthesis of 8-fluoro-3,4-dihydroisoquinoline is described below, based on a directed ortho -lithiation reaction. This key intermediate was then applied in various transformations. Fluorine–amine exchange afforded the corresponding 8-amino-3,4-dihydroisoquinolines, suitabl... Full description

Journal Title: Molecules (Basel Switzerland), May 26, 2018, Vol.23(6)
Main Author: Hargitai, Csilla
Other Authors: Nagy, Tamás , Halász, Judit , Simig, Gyula , Volk, Balázs
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1420-3049 ; DOI: 10.3390/molecules23061280
Link: http://search.proquest.com/docview/2049940644/?pq-origsite=primo
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recordid: proquest2049940644
title: Synthesis of 8-Fluoro-3,4-dihydroisoquinoline and Its Transformation to 1,8-Disubstituted Tetrahydroisoquinolines.
format: Article
creator:
  • Hargitai, Csilla
  • Nagy, Tamás
  • Halász, Judit
  • Simig, Gyula
  • Volk, Balázs
subjects:
  • Alkylation–Chemical Synthesis
  • Cyclization–Chemistry
  • Isoquinolines–Chemistry
  • Molecular Structure–Chemistry
  • Oxidation-Reduction–Chemistry
  • Tetrahydroisoquinolines–Chemistry
  • G 1616
  • Isoquinolines
  • Tetrahydroisoquinolines
  • Alkylation
  • Cyclization
  • Isoquinoline
  • Lithiation
  • Nucleophilic Aromatic Substitution
  • Reduction
ispartof: Molecules (Basel, Switzerland), May 26, 2018, Vol.23(6)
description: A simple procedure for the synthesis of 8-fluoro-3,4-dihydroisoquinoline is described below, based on a directed ortho -lithiation reaction. This key intermediate was then applied in various transformations. Fluorine–amine exchange afforded the corresponding 8-amino-3,4-dihydroisoquinolines, suitable starting compounds for the synthesis of 1-substituted 8-amino-tetrahydroisoquinolines. On the other hand, reduction and alkylation reactions of 8-fluoro-3,4-dihydroisoquinoline led to novel 1,2,3,4-tetrahydroisoquinoline derivatives that can be used as building blocks in the synthesis of potential central nervous system drug candidates.
language: eng
source:
identifier: E-ISSN: 1420-3049 ; DOI: 10.3390/molecules23061280
fulltext: fulltext
issn:
  • 14203049
  • 1420-3049
url: Link


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titleSynthesis of 8-Fluoro-3,4-dihydroisoquinoline and Its Transformation to 1,8-Disubstituted Tetrahydroisoquinolines.
creatorHargitai, Csilla ; Nagy, Tamás ; Halász, Judit ; Simig, Gyula ; Volk, Balázs
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ispartofMolecules (Basel, Switzerland), May 26, 2018, Vol.23(6)
identifierE-ISSN: 1420-3049 ; DOI: 10.3390/molecules23061280
subjectAlkylation–Chemical Synthesis ; Cyclization–Chemistry ; Isoquinolines–Chemistry ; Molecular Structure–Chemistry ; Oxidation-Reduction–Chemistry ; Tetrahydroisoquinolines–Chemistry ; G 1616 ; Isoquinolines ; Tetrahydroisoquinolines ; Alkylation ; Cyclization ; Isoquinoline ; Lithiation ; Nucleophilic Aromatic Substitution ; Reduction
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descriptionA simple procedure for the synthesis of 8-fluoro-3,4-dihydroisoquinoline is described below, based on a directed ortho -lithiation reaction. This key intermediate was then applied in various transformations. Fluorine–amine exchange afforded the corresponding 8-amino-3,4-dihydroisoquinolines, suitable starting compounds for the synthesis of 1-substituted 8-amino-tetrahydroisoquinolines. On the other hand, reduction and alkylation reactions of 8-fluoro-3,4-dihydroisoquinoline led to novel 1,2,3,4-tetrahydroisoquinoline derivatives that can be used as building blocks in the synthesis of potential central nervous system drug candidates.
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