Copper-Catalyzed Oxidative C-C Cleavage of Carbohydrates: An Efficient Access to Quinazolinone Scaffolds

A copper-catalyzed oxidative coupling strategy has been developed for the synthesis of 4(3H)-quinazolinones and benzoimidazoquinazoline using glucose as renewable C-1 synthon. Isotope labelling studies using C-13(6) D-glucose and DMSO-d(6) confirmed the role of D-glucose as C-1 source. The significant features of this method include (i) utilization of 0.25 to 0.5 equiv., of D-glucose as a multi-C-1 synthon; (ii) biomass-derived platform chemical as carbon synthon; (iii) atom-economical and benign conditions and; (iv) synthesis of naturally occurring alkaloid and precursor.

Automated summary

A copper-catalyzed oxidative coupling strategy has been developed for the synthesis of 4(3H)-quinazolinones and benzoimidazoquinazoline using glucose as a renewable C-1 synthon. Isotope labelling studies confirmed the role of glucose as a C-1 source, with significant features including the utilization of glucose as a multi-C-1 synthon, biomass-derived platform chemical as a carbon synthon, atom-economical conditions, and the synthesis of naturally occurring alkaloid and precursor.