| 摘要 |
1,208,114. Tetraazaphenalenes. J. R. GEIGY A.G. 2 Oct., 1967 [3 Oct., 1966], No. 44679/67. Heading C2C. Compounds of the Formula I wherein R 1 represents a hydrogen atom or an alkyl C 1-4 or phenyl radical, R 2 represents a hydrogen atom or a phenyl radical, R 3 represents a hydrogen, chlorine or bromine atom, or an alkoxy C 1-4 , carboxyl or hydroxyl radical are prepared by eliminating the radical X from a compound of the Formula II wherein X is a chlorine or bromine atom or a mercapto or hydrazine radical, the elimination being performed by known methods and, when required, converting the 1,2,8,9 - tetraazaphenalene so obtained into a pharmaceutically acceptable addition salt with an organic or inorganic acid, or transforming it with a lower alkylating agent into a quaternary ammonium compound. Known methods described include (1) when X is a halogen atom the compound of Formula II is reduced using either hydroiodic acid or catalytically activated hydrogen or (2) when X is the mercapto radical the compound of Formula II is treated with catalytically activated nickel or (3) when X is the hydrazine radical the compound of Formula II is treated with an aqueous solution of pH between 7 and 8À5 in the presence of a cuprous salt.α,α- Dibromo - 3 - methyl phthalic anhydride is prepared from 3 - methylphthalic anhydride and N - bromosuccinamide. It is converted by treatment with hydrazine hydrate to 3 - hydroxy - 1,2,8,9 - tetraazaphenalene. This is converted to 3 - chloro - 1,2,8,9 - tetraazaphenalene by reaction with phosphoryl chloride. 3 - Mercapto - 1,2,8,9 - tetraazaphenalene is obtained by reaction of the 3 - hydroxy compound with phosphorus pentasulphide. 3 - hydrazino - 1,2,8,9 - tetraazaphenalene dihydrochloride is obtained from the 3 - chloro compound and hydrazine hydrate in the presence of hydrochloric acid. 7 - Carboxy - 3 - hydroxy phthalide is prepared fromα,α- dibromo - 3 - methylphthalic anhydride and sodium hydroxide. 8 - Carboxy - 2 - phenyl - 1(2H)phthalazinone is prepared from hydrazine and 7 - carboxy - 3 - hydroxy phthalide. The carbomethoxy and carboethoxy derivatives are prepared by esterification. |
