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Note | Regular issue | Vol 78, No. 5, 2009, pp.1289-1298
Published online, 29th January, 2009
DOI: 10.3987/COM-08-11622
Acyl and Sulfonyl Derivatives of 10-Aminoalkyl-2,7-diazaphenothiazines

Beata Morak-Młodawska and Krystian Pluta*

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

Abstract

Reaction of 3,3’-dinitro-4,4’-dipyridinyl disulfide (1) with sodium hydroxide in DMF led to 10H-2,7-diazaphenothiazine (4). N-Alkylation of (4) with phthalimidopropyl and phthalimidobutyl bromides gave phthalimidoalkyl derivatives (5) and (6) which were hydrolyzed to aminoalkyldiazaphenothiazines (7) and (8). N-Acylation with acetyl anhydride, benzoyl chloride, ethyl chloroformate and 2-chloroethyl isocyanate gave N-acyl derivatives (9-16). N-Sulfonylation with methanesulfonyl and p-toluenesulfonyl chlorides led to N-sulfonyl derivatives (17-20).