Litcius/Paper detail

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

Zixian Yang, Yujia Shan, Jin‐Tao Yu, Changduo Pan

2021European Journal of Organic Chemistry21 citationsDOI

Abstract

Abstract 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.

Topics & Concepts

ChemistryRadical cyclizationRing (chemistry)Free-radical reactionRadical initiatorQuinazolinoneCombinatorial chemistryPeroxideFree-radical additionRadicalOrganic chemistryMonomerPolymerQuinazolinone synthesis and applicationsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions