52462-89-2Relevant academic research and scientific papers
Syntheses of 2-Iminoindolin-3-ones and 2-Alknyl-2,3-dihydroquinazolin-4(1 H)-ones from 3-Diazoindolin-2-imines
Lin, Zhenwei,Qian, Jing,Lu, Ping,Wang, Yanguang
, p. 11766 - 11777 (2020/10/23)
3-Diazoindolin-2-imines reacted with nitrones to furnish 2-iminoindolin-3-ones through a Au(I)-catalyzed cascade oxygen transfer/imine exchange process. The prepared 2-iminoindolin-3-ones could be further transformed into 2-Alknyl-2,3-dihydroquinazolin-4(1H)-ones through a Ag(I)-catalyzed reaction with terminal alkynes. A MeOH-Triggered ring expansion mechanism involving cyclic iminium formation and nucleophilic addition is proposed for this novel alkynylation reaction. This two-step procedure provides a general and convenient approach to 2-Alknyl-2,3-dihydroquinazolin-4(1H)-ones, which are privileged structures in medicinal chemistry.
