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A radical di‐ and trichloromethylation/cyclization of unactivated alkenes was developed with commercially available dichloromethane and chloroform as di‐and trichloromethyl radical sources under metal‐free conditions. Variously substituted di‐ and trichloromethylated pyrrolo‐ and piperidino‐quinazolinones were obtained in 47–94% yields. Additionally, dibromomethylation/cyclization was also achieved under standard conditions when CH2Br2 was utilized. Moreover, the obtained dichloromethylated product can be transformed into 1′H‐spiro[cyclopropane‐1,3′‐pyrrolo[2,1‐b]quinazolin]‐9′(2′H)‐one after treating by KOH. [ABSTRACT FROM AUTHOR]

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(sp3)−H functionalization of simple alcohols and was successfully utilized in the synthesis of Phaitanthrin A derivative. [ABSTRACT FROM AUTHOR]