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8β‐Substituted dihydrocodeinones having heteroatoms in the side chain
Author(s) -
Kotick Michael P.,
Polazzi Joseph O.
Publication year - 1981
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570180535
Subject(s) - chemistry , nitromethane , heteroatom , side chain , adduct , methanol , hydroxymethyl , fluoride , organic chemistry , medicinal chemistry , ring (chemistry) , inorganic chemistry , polymer
A series of 8β‐substituted dihydrocodeinones, having hetero atoms in the side chain, were prepared. Michael addition of methanol or ethanol to 1 was accomplished under basic conditions, while the nitromethane adduct was prepared by a fluoride ion catalyzed reaction. The 8β‐diethylmalonyl adduct 7 was converted in several steps to an 8β‐tertiary carbinol analog 12 . Alternatively, 8β‐vinyldihydrocodeinone 13 was transformed, via the dimethyl ketal, to 8β‐hydroxymethyl or ‐ethyl compounds which were fluorinated in the side chain by use of diethylaminosulfur trifluoride.