Synthesis of 5,6‐Dimethylbenz[a]phenazine | Zendy

Cromwell N. H. | Zendy; Desai H. S. | Zendy; Pokorny D. J. | Zendy

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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.

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