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Synthesis and stereochemical analysis of isomeric N ‐substituted 5‐ and 6‐propanilido‐2‐azabicyclo[2.2.2]octanes
Author(s) -
Law SayJong,
Lewis Daniel H.,
Borne Ronald F.
Publication year - 1978
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.5570150218
Subject(s) - chemistry , reagent , octane , stereochemistry , bicyclic molecule , hydrogen bond , medicinal chemistry , organic chemistry , combinatorial chemistry , molecule
The synthesis and stereochemical analysis of N ‐methyl and N ‐phenethyl‐substituted 5‐ and 6‐propanilido derivatives of 2‐azabicyclo[2.2.2]octane were investigated for potential evaluation as analgesics related to fentanyl. Stereochemical assignments for the eight isomers reported here were made on the basis of nmr studies employing europium chemical shift reagents and hydrogen bonding studies employing ir analysis of the anilino‐ and propanilido‐derivatives.