Copper-Catalyzed C-H Arylation of Fused-Pyrimidinone Derivatives Using Diaryliodonium Salts

Copper-catalyzed Csp2-Csp2 bond forming reactions through C-H activation are still one of the most useful strategies for the diversification of heterocyclic moieties using various coupling partners. A catalytic protocol for the C-H (hetero)arylation of thiazolo[5,4-f]quinazolin-9(8H)-ones and more generally fused-pyrimidinones using catalyst loading of CuI with diaryliodonium triflates as aryl source under microwave irradiation has been disclosed. The selectivity of the transfer of the aryl group was also disclosed in the case of unsymmetrical diaryliodonium salts. Specific phenylation of valuable fused-pyrimidinones including quinazolinone are provided. This strategy enables a rapid access to an array of various (hetero)arylated N-containing polyheteroaromatics as new potential bioactive compounds.

Automated summary

The copper-catalyzed Csp2-Csp2 bond forming reactions through C-H activation offer a useful strategy for the diversification of heterocyclic moieties. Specific phenylation of fused-pyrimidinones, including quinazolinone, has been achieved using this method, leading to the rapid access of various arylated N-containing polyheteroaromatics as potential bioactive compounds.