Metal-Free Synthesis of Anthranils by PhIO Mediated Heterocyclization of ortho-Carbonyl Anilines

被引:8
|
作者
Garia, Alankrita [1 ]
Grover, Jatin [1 ]
Jain, Nidhi [1 ]
机构
[1] Indian Inst Technol, Dept Chem, New Delhi 110016, India
关键词
Heterocyclization; Iminoiodane; Iodosyl benzene; Metal-free; Nitrene; ortho-Carbonyl anilines; N-O; 2,1-BENZISOXAZOLES ANTHRANILS; OXIDATIVE CYCLIZATION; BOND FORMATION; INHIBITORS; ACID; BENZISOXAZOLE; CONSTRUCTION; REACTIVITY; NITRILES;
D O I
10.1002/ejoc.202100756
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Here, we report a metal-free synthesis of anthranils from ortho-carbonyl anilines using PhIO as a sole additive under ambient conditions. This methodology did not require any external additives and delivered anthranils in excellent yields with broad substrate scope. The mechanistic studies suggest that the reaction proceeds via in-situ generation of iminoiodane leading to nitrene and a subsequent nucleophilic attack from oxygen of ortho-carbonyl aniline on nitrene results in heterocyclization.
引用
收藏
页码:4125 / 4131
页数:7
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