Apomorphinans from Isoquinolines:  Grewe  cyclization of 1‐(2‐hydroxybenzyl)‐ N ‐methyloctahydroisoquinoline and its  O ‐methyl ether | Zendy

Schmidhammer Helmut | Zendy; Brossi Arnold | Zendy; FlippenAnderson Judith L. | Zendy; Gilardi Richard | Zendy

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Apomorphinans from Isoquinolines: Grewe cyclization of 1‐(2‐hydroxybenzyl)‐ N ‐methyloctahydroisoquinoline and its O ‐methyl ether

Author(s) -

Schmidhammer Helmut,

Brossi Arnold,

FlippenAnderson Judith L.,

Gilardi Richard

Publication year - 1983

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.19830660807

Subject(s) - chemistry , hydrobromide , isoquinoline , hydrobromic acid , ether , medicinal chemistry , optically active , amine gas treating , salt (chemistry) , organic chemistry

Wolff ‐ Kishner reduction of the optically active ketomorphinan 5 afforded the optically active morphinan 6 differing chromatographically and spectroscopically from the material obtained in a Grewe ‐cyclization of the isoquinoline 1 . A single crystal X‐ray analysis of a hydrobromide salt of a phenolic amine obtained from 1 and 2 with refluxing hydrobromic acid showed this compound to be the N ‐methylapomorphinan 4 .

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