Splitting Methyl Ketones into Two Parts: Synthesis of 4(3<i>H</i>)-Quinazolinones via Consecutive Cyclization/Ring-Opening Reaction
Peng Zhao, Xiaoxiao Yu, You Zhou, Xiao Geng, Can Wang, Chun Huang, Yan‐Dong Wu, Yanping Zhu, An‐Xin Wu
Abstract
The first synthesis of arylquinazolinones has been disclosed via the consecutive oxidative cyclization/ring-opening of anilines and methyl ketones. This transformation is characterized by the splitting of the methyl ketone as acyl and C1 sources through C(CO)–C(sp3) bond cleavage, using DMSO as a C1 source via C–S bond cleavage, which expands the use of methyl ketones as valuable building blocks and enriches the library of preparation quinazolinones. Moreover, preliminary mechanistic studies indicate that this multicomponent reaction underwent a consecutive cyclization/ring-opening sequence.
Topics & Concepts
ChemistryRing (chemistry)Medicinal chemistryStereochemistryCombinatorial chemistryOrganic chemistryQuinazolinone synthesis and applicationsAdvanced Synthetic Organic ChemistryCatalytic C–H Functionalization Methods