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We describe the preparation of new substituted dioxolo(4,5-b)phenothiazines by two slightly different reaction sequences. N-Arylation of (1,3)benzodioxol-5-amine with organolead or organobismuth reagents afforded N-aryl(1,3)benzodioxol-5-amines; subsequent Bernthsen thionation gave rise to phenothiazine ring formation and was followed by N-acylation. On the other hand, (1,3)benzodioxol-5-amine was first N-alkylated, the resulting N- alkyl(1,3)benzodioxol-5-amines were N-phenylated, before Bernthsen the final tetracyclic thionation furnished product.

Regioselective synthesis of N-acyl- and N-alkyldioxolo[4,5-b]phenothiazines