Rhodium-Catalyzed Intramolecular Cyclization and Rearrangement of 1-Azido-2-(2,2-Dihalovinyl)arenes and 1-Azido-2-[(2,2-Dihalovinyl)(Boc)amino]arenes for the Preparation of 2,3-Dihaloindoles and 2-Haloquinoxalines

被引:0
作者
Abe, Teppei [1 ]
Kobayashi, Kazuki [1 ]
Kikukawa, Seiya [1 ]
Kanai, Yuuki [1 ]
Hata, Takeshi [1 ]
机构
[1] Tokyo Inst Technol, Sch Life Sci & Technol, Dept Life Sci & Technol, 4259-B-59 Nagatsuta Cho,Midori Ku, Yokohama, Kanagawa 2268501, Japan
关键词
aryl azide; dihalovinyl group; indole; nitrene; rhodium; quinoxaline; ONE-POT SYNTHESIS; C-H AMINATION; QUINOXALINE;
D O I
10.1002/adsc.202300885
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Treatment of 1-azido-2-(2,2-dihalovinyl)arenes with a catalytic amount of Rh2(esp)2 afforded various 2,3-dihaloindoles in 51-74% yields. This reaction progressed via the intramolecular cyclization of rhodium nitrene generated in situ and the rearrangement of one halogen group. For the 2-chloro-2-iodovinyl group, the iodo group selectively rearranged to yield 2-chloro-3-iodoindoles as single isomers. Moreover, 1-azido-2-[(2,2-dihalomovinyl)(Boc)amino]arenes were reacted with a catalytic amount of Rh2(oct)4, which produced 2-haloquinoxaline in 55-92% yields. image
引用
收藏
页码:4562 / 4566
页数:5
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