Quinazolinones have great importance in medicinal chemistry. They possess wide spectrum of biological activities and were found to have antibacterial, antifungal, anticonvulsant, anti-inflammatory, anti-HIV, anti-cancer and analgesic effects. Quinazolinones are privileged structures and the number of synthetic methods to access this core structure have increased immensely from year to year, which make it versatile building blocks. We have developed a metal-free C(sp3)-H/C(sp3)-H cross-dehydrogenative coupling (CDC) method to synthesize enone derivatives of quinazolinones. The new method involves the use of iodine in DMSO to mediate the oxidative coupling process to produce the desired products in high yields under mild reaction conditions. This synthesis is single step, requires easy work-up, and will provide excellent platform for diversification of methyl-substituted heterocyclic systems.

Metal free C(sp3)-H/C(sp3)-H cross-dehydrogenative coupling (CDC) of 2-methyl quinazolinones with methyl ketones

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ACS Fall 2022

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