Three-Component Domino Synthesis of 2-Arylquinazoline-4-amines in One Pot by Activating an sp3 C–H Bond in a Nonmetal Catalytic Oxidation System

✍ Scribed by Li-Yan Zeng; Wen-Bin Yi; Chun Cai

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 636 KB
• Volume: 2012
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/ejoc.201101315

✦ Synopsis

Abstract

The nonmetal catalytic oxidation system I~2~/tert‐butyl hydroperoxide (TBHP) has been unprecedentedly applied to a three‐component domino reaction and simultaneously a simple and efficient protocol has been developed to newly synthesize 2‐aryl‐N‐substitutied quinazoline‐4‐amines in one pot from isatoic anhydride, aromatic amine, and another amine containing methylene adjacent to nitrogen. This protocol is new and practical because both the electron‐donating and ‐withdrawing groups substituted on amines 2 or 3 can survive and provide the corresponding products in reasonable yields. Iodine is essential to the three‐component, one‐pot reaction unlike the step‐wise procedure.