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Synthesis and stereochemical assignment of 7‐arylidene and 7‐heteroarylidene morphinan‐6‐ones
Author(s) -
Nan Yang,
Upadhyaya Subhash P.,
Xu Wei,
Hughes Kathrine E.,
Dunn William J.,
Bauer Ludwig,
Bhargava Hemendra N.,
Doss George A.
Publication year - 1996
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.5570330231
Subject(s) - chemistry , benzaldehyde , piperidine , aldehyde , sodium hydroxide , condensation , organic chemistry , dimethyl sulfoxide , methanol , medicinal chemistry , catalysis , stereochemistry , physics , thermodynamics
A number of ( E )‐7‐arylidenenaltrexones were synthesized by azeotropic distillation of water from a benzene solution of naltrexone and an aromatic aldehyde (benzaldehyde, 4‐chloro‐ and 4‐fluorobenzaldehyde, 3‐and 4‐pyridinecarboxaldehyde and 1‐methyl‐2‐imidazolecarboxaldehyde) using piperidine as a catalyst. In addition, ( E )‐7‐benzylidenenaloxone was prepared by the previously published Claisen‐Schmidt condensation using sodium hydroxide in methanol. The stereochemistry of these arylidene derivatives 3–9 was determined to be ( E ) by means of nuclear Overhauser enhancement experiments. The 13 C nmr spectra of ( E )‐ 3–9 are recorded in deuteriochloroform and those of the hydrochlorides in deuteriodimethyl sulfoxide.