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Studies in the heterocyclic series. XX. 1,4‐Diazaphenoxazine and related compounds
Author(s) -
Okafor Charles O.
Publication year - 1981
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.5570180732
Subject(s) - chemistry , phenoxazine , nitration , sulfuric acid , nitric acid , organic chemistry , medicinal chemistry , combinatorial chemistry , medicine , phenothiazine , pharmacology
As part of our program on the synthesis of new psychotropic agents, the parent rings of two diazaphenox‐azines are described. The reaction of 2‐aminophenol and 2,3‐dichloropyrazine in alkaline media gave good yields of 1,4‐diazaphenoxazine. Replacement of 2,3‐dichloropyrazine with 2,3‐dichloroquinoxaline gave on the other hand the heterocycle, 1,4‐diazabenzo[ b ]phenoxazine. Nitration and S ‐oxide formation were achieved by reaction with mixed nitric and sulfuric acids. Mechanistic pathways to these compounds were also discussed.