Metal-Free Photoinduced Hydrocyclization of Unactivated Alkenes toward Ring-Fused Quinazolin-4(3<i>H</i>)-ones via Intermolecular Hydrogen Atom Transfer
Zixian Yang, Xian Wu, Jie Zhang, Jin‐Tao Yu, Changduo Pan
Abstract
A visible-light-induced hydrocyclization of unactivated alkenes was developed using 3CzClIPN as the photocatalyst to generate substituted α-methyldeoxyvasicinones and α-methylmackinazolinones in moderate to good yields. An intermolecular hydrogen atom transfer with THF as the hydrogen source was involved. Mechanism studies indicated that the intramolecular addition of the in situ formed aminal radical to the unactivated alkene generated the polycyclic quinazolinone.
Topics & Concepts
ChemistryIntramolecular forceIntermolecular forceHydrogen atomAlkeneQuinazolinonePhotochemistryRing (chemistry)MetalHydrogenAtom (system on chip)MoleculeStereochemistryOrganic chemistryCatalysisAlkylComputer scienceEmbedded systemQuinazolinone synthesis and applicationsRadical Photochemical ReactionsCatalytic C–H Functionalization Methods