Copper Catalysed N-Arylation of Angular Triazaphenothiazinone

Abstract

The copper catalyzed N-arylation of angular aminotriazaphenothiazinone is reported. This was achieved by the coupling of 11-amino-1,8,10-triazabenzo[a]phenothiazin-5-one with potassium or lithium aryltriolborate in the presence of a copper catalyst  for over 20h at room temperature to give the desired product. The success of this reaction lies in the preparation of the key intermediate, 11-amino-1, 8, 10-triazabenzo[a]phenothiazin-5-one synthesized by the condensation of 4, 5-diamino-6-thioprimidine with 7-chloro-5, 8-quinolinequinone in an anhydrous basic medium. Structures were assigned on the basis of spectral and analytical data.

Keywords: Aminotriazaphenothiazinone, triazabenzo[a]phenothiazinone, aryltriolborate, diaminothioprimidine.