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Synthesis of 1α and 1β‐acylamino and alkylamino‐1,2,3,4,5,6‐hexahydro‐2,6‐methano‐3‐benzazocines and related compounds
Author(s) -
Hirani Shabir K.,
Parfitt Robert T.
Publication year - 1987
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.5570240235
Subject(s) - chemistry , steric effects , derivative (finance) , stereochemistry , alkyl , medicinal chemistry , organic chemistry , financial economics , economics
The synthesis of series of 1α and 1β‐alkylamino‐1,2,3,4,5,6‐hexahydro‐2,6‐methano‐3‐benzazocines from the corresponding acylamino intermediates is described. Cyclization of the 1β‐chloromethylamido derivative 20 to the novel bridged benzomorphan 21 occurred whereas the corresponding 1β‐chloromethylamido derivative 19 failed to cyclize for steric reasons. In addition several related 1α‐acylamidomethyl‐ and 1β‐alkyl‐aminomethyl benzomorphans are reported.