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A Novel Synthesis of Substituted 1-Benzyloctahydroisoquinolines by Acid-Catalyzed Cyclization of N-[2-(Cyclohex-1-enyl)ethyl]-N-styrylformamides

✍ Scribed by Gerrit J. Meuzelaar; Ernst Neeleman; Leendert Maat; Roger A. Sheldon

Publisher: John Wiley and Sons
Year: 1998
Tongue: English
Weight: 209 KB
Volume: 1998
Category: Article
ISSN: 1434-193X
DOI: 10.1002/(sici)1099-0690(199810)1998:10<2101::aid-ejoc2101>3.0.co;2-x

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✦ Synopsis

The acid-catalyzed cyclization of N- [2-(cyclohex-1-octahydroisoquinoline formed was accompanied by minor concentrations of one, two, or three isomeric octa-enyl)ethyl]-N-styrylformamides 1-5 gave access to 1-benzyl-2-formyloctahydroisoquinolines 6-10. The reactions were hydroisoquinolines. 1-Benzyl-2-formyloctahydroisoquinoline (6) could also be prepared from N-[2-(cyclohex-1-enyl)-performed in the presence of the Lewis acid 9-borabicyclo[3.3.1]non-9-yl triflate. The cyclization of enamide 1 ethyl]formamide (11) by reaction with phenylacetaldehyde in a mixture of acetic acid and trifluoroacetic acid. The was also studied with Brønsted acid catalysts, such as triflic acid and the heterogeneous catalyst tungstophosphoric acid octahydroisoquinolines 6, 8, 10 as model compounds, were converted into the corresponding N-formylmorphinans. supported on silica gel. In all cases the 1,2, 3,4,5,6,7,8-

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