Synthesis and stereochemical assignment of 7‐arylidene and 7‐heteroarylidene morphinan‐6‐ones | Zendy

Nan Yang | Zendy; Upadhyaya Subhash P. | Zendy; Xu Wei | Zendy; Hughes Kathrine E. | Zendy; Dunn William J. | Zendy; Bauer Ludwig | Zendy; Bhargava Hemendra N. | Zendy; Doss George A. | Zendy

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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.

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