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Author | dc.contributor.author | Sobarzo Sánchez, Eduardo | |
Author | dc.contributor.author | Castedo, Luis | |
Author | dc.contributor.author | Fuente, Julio de la | |
Admission date | dc.date.accessioned | 2018-12-20T14:11:09Z | |
Available date | dc.date.available | 2018-12-20T14:11:09Z | |
Publication date | dc.date.issued | 2007 | |
Cita de ítem | dc.identifier.citation | Synthetic Communications, Volumen 37, Issue 8, 2018, Pages 1331-1338 | |
Identifier | dc.identifier.issn | 00397911 | |
Identifier | dc.identifier.issn | 15322432 | |
Identifier | dc.identifier.other | 10.1080/00397910701227168 | |
Identifier | dc.identifier.uri | https://repositorio.uchile.cl/handle/2250/154480 | |
Abstract | dc.description.abstract | 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. | |
Lenguage | dc.language.iso | en | |
Type of license | dc.rights | Attribution-NonCommercial-NoDerivs 3.0 Chile | |
Link to License | dc.rights.uri | http://creativecommons.org/licenses/by-nc-nd/3.0/cl/ | |
Source | dc.source | Synthetic Communications | |
Keywords | dc.subject | 1-(pyridin-3-yl)isoquinoline | |
Keywords | dc.subject | Anabaseine | |
Keywords | dc.subject | Anabasine | |
Keywords | dc.subject | Nicotinic acetylcholine receptor | |
Título | dc.title | Synthesis of anabaseine and anabasine derivatives: Structural modifications of possible nicotinic agonists | |
Document type | dc.type | Artículo de revista | |
Cataloguer | uchile.catalogador | SCOPUS | |
Indexation | uchile.index | Artículo de publicación SCOPUS | |
uchile.cosecha | uchile.cosecha | SI | |
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