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Synthesis of anabaseine and anabasine derivatives: Structural modifications of possible nicotinic agonists

By Eduardo Sobarzo Sánchez, Luis Castedo and Julio De la Fuente


Coupling nicotinoyl chloride with 3,4-dimetoxyphenethylamine under Bischler-Napieralski cyclization afforded the isoquinoline (4) in good yield. This latter was used as starting material to obtain with only hydrobromic acid a product with demethylation at the position 7 (5). In addition, treatment of (4) with NaBH4/MeOH gave 6,7-dimetoxy-1-(pyridin-3-yl)-1,2,3,4- tetrahydroisoquinoline (6) and unexpectedly, under mild reduction of the pyridine moiety with H2/PtO2/AcOH/, gave 6,7-dimetoxy-1-(piperidin-3-yl)-1,2,3, 4-tetrahydroisoquinoline (7) as the title compound. The unusual chemical reactivity of 4 onto acidic conditions and catalytic hydrogenation allowed us to obtain anabaseine and anabasine derivatives under mild conditions. Copyright © Taylor & Francis Group, LLC

Topics: 1-(pyridin-3-yl)isoquinoline, Anabaseine, Anabasine, Nicotinic acetylcholine receptor
Publisher: 'Informa UK Limited'
Year: 2007
DOI identifier: 10.1080/00397910701227168
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