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- Title
Synthesis of 8-Fluoro-3,4-dihydroisoquinoline and Its Transformation to 1,8-Disubstituted Tetrahydroisoquinolines.
- Authors
Hargitai, Csilla; Nagy, Tamás; Halász, Judit; Simig, Gyula; Volk, Balázs; Bunce, Richard A.; Belmont, Philippe; Dehaen, Wim; Babaev, Eugene
- Abstract
A simple procedure for the synthesis of 8-fluoro-3,4-dihydroisoquinoline is described below, based on a directed <italic>ortho</italic>-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.
- Subjects
TETRAHYDROISOQUINOLINES; CHEMICAL synthesis; LITHIATION; CHEMICAL reactions; RING formation (Chemistry); ANTINEOPLASTIC agents
- Publication
Molecules, 2018, Vol 23, Issue 6, p1280
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules23061280