Copper-Catalyzed Arylation Reaction in the Synthesis of New Derivatives of Angular Triazaphenoxazinone

Abstract

The synthesis of 11-(N-substituted)-angular triazaphenoxazinone via copper catalyzed N-arylation reaction is reported. The key intermediate, 7-chloro-5, 8-quinolinequinone was obtained in a five-step reaction, starting from 8-hydroxyquinoline. This was coupled with 4, 5-diamino-6-hydroxypyrimidine, in the presence of sodium acetate under anhydrous condition to afford 11-amino-1, 8, 10-triazabenzo[a]phenoxazin-5-one. The new derivatives were obtained by the reaction of 11-amino-1, 8, 10-triazabenzo[a]phenoxazin-5-one with substituted potassium/lithium phenyltriolborates, under the catalytic influence of copper (II) acetate in the presence of trimethylamine N-oxide, and 4Å molecular sieve. Products were obtained in good yield (70-80%). Structures were established by spectra and analytical data. These tetracyclic heterocycles absorb light in the visible region (400-700nm), which makes them applicable as laser dyes.

Keywords: synthesis, triazaphenoxazinone, copper catalyzed N-arylation reaction