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Paper | Regular issue | Vol 81, No. 11, 2010, pp.2511-2522
Published online, 8th September, 2010
DOI: 10.3987/COM-10-12007
Alkylations of 10H-2,7-Diazaphenothiazine to Alkyl-2,7-diazaphenothiazinium Salts and 7-Alkyl-2,7-diazaphenothiazines

Beata Morak-Młodawska, Krystian Pluta,* Kinga Suwińska, and Małgorzata Jeleń

*Department of Organic Chemistry, The Medical University of Silesia, Jagielloñska Str. 4, 41-200 Sosnowiec, Poland


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-diazapheno-thiazinium 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-diazaphe-nothiazidiinium dihalides (5) and (8) were transformed into 7-alkyl-2,7-diazaphe-nothiazines (9) and (12) in basic conditions. The structures of the products were determined on the basis of physical properties, 1H NMR (ROESY, COSY) and MS spectra, and were confirmed by X-ray analysis of compounds (3-5).