Metal-Free Hydroxyalkylative Radical Addition/Cyclization of Unactivated Alkenes for the Synthesis of Hydroxyalkylated Ring-Fused Quinazolinones

An efficient protocol for the synthesis of ring-fused quinazolinone derivatives through hydroxyalkyl radical-initiated cyclization was developed, providing a series of five- and six-membered ring-fused hydroxyl-containing quinazolinones in moderate to good yields. This reaction was conducted under metal-free conditions using dicumyl peroxide as the radical initiator. Notably, this is the first example of the construction of ring-fused quinazolinones through the radical C(sp(3))-H functionalization of simple alcohols and was successfully utilized in the synthesis of Phaitanthrin A derivative.