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Molecules 2018, 23(6), 1280; https://doi.org/10.3390/molecules23061280

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

Directorate of Drug Substance Development, Egis Pharmaceuticals Plc., P.O. Box 100, H-1475 Budapest, Hungary
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Academic Editors: Richard A. Bunce, Philippe Belmont, Wim Dehaen and Eugene Babaev
Received: 28 April 2018 / Revised: 17 May 2018 / Accepted: 22 May 2018 / Published: 26 May 2018
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

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. View Full-Text
Keywords: isoquinoline; lithiation; nucleophilic aromatic substitution; reduction; alkylation; cyclization isoquinoline; lithiation; nucleophilic aromatic substitution; reduction; alkylation; cyclization
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).
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Hargitai, C.; Nagy, T.; Halász, J.; Simig, G.; Volk, B. Synthesis of 8-Fluoro-3,4-dihydroisoquinoline and Its Transformation to 1,8-Disubstituted Tetrahydroisoquinolines. Molecules 2018, 23, 1280.

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