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Bridged 1,4‐benzoxazocines from 5‐hydroxy‐3‐phenyl‐2‐benzofuranone
Author(s) -
Zaugg H. E.,
Holland J. B.,
Dunnigan D. A.,
Denet R. W.
Publication year - 1974
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.5570110619
Subject(s) - chemistry , ring (chemistry) , stereochemistry , series (stratigraphy) , group (periodic table) , analogy , medicinal chemistry , organic chemistry , paleontology , linguistics , philosophy , biology
A previously described neighboring group reaction has been extended to the synthesis of hydroxy‐substituted bridged 1,4‐benzoxazocines ( i.e. , 7, 8 ) bearing a structural analogy to potent analgetics of the hydroxy‐6,7‐benzomorphan series. In contrast to the latter, the presence of a hydroxyl group in the aromatic ring of the present series destroys all analgesic activity possessed by the unsubstituted system.