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Three‐Component Domino Synthesis of 2‐Arylquinazoline‐4‐amines in One Pot by Activating an sp 3 C–H Bond in a Nonmetal Catalytic Oxidation System
Author(s) -
Zeng LiYan,
Yi WenBin,
Cai Chun
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201101315
Subject(s) - chemistry , domino , catalysis , amine gas treating , nonmetal , methylene , quinazoline , organic chemistry , component (thermodynamics) , aryl , nitrogen , medicinal chemistry , combinatorial chemistry , physics , alkyl , metal , thermodynamics
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.