AKYLATIONS OF 10H-2,7-DIAZAPHENOTHIAZINE TO ALKYL-2,7-DIAZAPHENOTHIAZINIUM SALTS AND 7-ALKYL-2,7-DIAZAPHENOTHIAZINES

Alkylations of 10H-2,7-diazaphenothiazine (1) with alkyl halides led to different products depending on the reaction conditions: 10-methyl derivative (2), 2,10-dimethyl-2,7-diazaphenothiazinium and 7,10-dimethyl-2,7-diazaphenothiazinium iodides (3-4), 2,7-dialkyl-2,7-diazaphenothiazidiinium dihalides (5-8) and 7-alkyl-2,7-diazaphenothiazines (9-12). The last compounds were the isomers of recently published 10-alkyl-2,7-diazaphenothiazines. 2,7-Dialkyl-2,7-diazaphenothiazidiinium dihalides (5) and (8) were transformed into 7-alkyl-2,7-diazaphenothiazines (9) and (12) in basic conditions. The structures of the products were determined on the basis of physical properties, H-1 NMR (ROESY, COSY) and MS spectra, and were confirmed by X-ray analysis of compounds (3-5).