Radical Polychloromethylation/Cyclization of Unactivated Alkenes: Access to Polychloromethyl‐Substituted Ring‐Fused Quinazolinones
Han Liu, Zixian Yang, Jin‐Tao Yu, Changduo Pan
Abstract
Abstract 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 CH 2 Br 2 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. magnified image
Topics & Concepts
ChemistryDichloromethaneCyclopropaneChloroformRadical cyclizationRing (chemistry)Medicinal chemistryCombinatorial chemistryOrganic chemistrySolventQuinazolinone synthesis and applicationsCatalytic C–H Functionalization MethodsRadical Photochemical Reactions