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Synthesis of 5,6‐dihydro‐8‐methoxy‐4 H ‐imidazo[4,5,1‐ ij ]quinolines and some related ring systems
Author(s) -
Werbel Leslie M.,
Battaglia Josephine,
Zamora Maria L.
Publication year - 1968
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.5570050311
Subject(s) - chemistry , ring (chemistry) , acetic acid , carbamate , medicinal chemistry , urea , oxide , platinum , stereochemistry , organic chemistry , catalysis
Reduction of amides of 8‐amino‐6‐methoxyquinoline over platinum oxide in glacial acetic acid at room temperature affords 2‐substituted‐5,6‐dihydro‐8‐methoxy‐4 H ‐imidazo [4,5,1‐ ij ]‐quinolines (I). The method could not be utilized for urea or carbamate derivatives of 8‐amino‐6‐methoxyquinoline. 2‐Amino derivatives of I were prepared through the chloro compound obtained from 5,6‐dihydro‐8‐methoxy‐4 H ‐imidazo[4,5,1‐ ij ]quinolin‐2(1 H )‐one, (IV). Several related ring systems have also been prepared.