Diaryliodonium salt as oxidant in sp3 C-H activation and synthesis of quinazolin-4(3H)-ones

Abstract

Reactions of 2-aminobenzamides with diaryliodonium salts in N,N-dimethylacetamide (DMA) led to the formation of unexpected product quinazoline-4(3H)-one derivatives instead of the desired N-arylated 2-aminobenzamides. Most likely the diaryliodonium salts activated the sp3 C-H of N-methyl group of DMA through oxidation thereby produced an iminium species, the reaction of which with 2-aminobenzamides caused the annulation.

Keywords

• Diphenyliodonium triflate
• Oxidative sp3 C-H activation
• Solvent DMA as one carbon source
• Quinazoline-4(3H)-ones