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Synthesis of 5,6‐Dimethylbenz[a]phenazine
Author(s) -
Cromwell N. H.,
Desai H. S.,
Pokorny D. J.
Publication year - 1976
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.5570130502
Subject(s) - phenazine , chemistry , acridine , alcohol , hydrolysis , dehydration , derivative (finance) , ketone , methyl ketone , organic chemistry , medicinal chemistry , biochemistry , financial economics , economics
5,6‐Dimethylbenz[ a ]phenazine ( 4 ), an aza analogue of the carcinogenic 5,6‐dimethylbenz‐[ c ]acridine has been obtained by a 1,1‐dehydration‐rearrangement (Wagner‐Meerwin type) from 5,5‐dimethyl‐6‐hydroxy‐5,6‐dihydrobenz[ a ]phenazine ( 3 ). The alcohol 3 was obtained from the hydrogenation of the corresponding ketone 2 which was prepared in two ways: Method A, the oxidation of 5,5‐dimethyl‐5,6‐dihydrobenz[ a ]phenazine ( 1 ); Method B, the hydrolysis of the 6,6‐dibromo derivative 5 of 1.