Simple and efficient procedures for selective preparation of 3-haloindoles and 2,3-dihaloindoles by using 1,3-dibromo-5, 5-dimethylhydantoin and 1,3-dichloro-5,5-dimethylhydantoin

被引：27

作者：

Yan, Jianwei ^{[1
]}

Ni, Tianjun ^{[2
]}

Yan, Fulin ^{[1
]}

机构：

[1] Xinxiang Med Univ, Sch Pharm, Xinxiang 453003, Henan, Peoples R China

[2] Xinxiang Med Univ, Dept Chem, Xinxiang 453003, Henan, Peoples R China

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 09期

关键词：

Indole; 1,3-Dibromo-5,5-dimethylhydantoin; 1,3-Dichloro-5,5-dimethylhydantoin; 3-Haloindole; 2,3-Dihaloindole; RED ALGA; LAURENCIA-BRONGNIARTII; BROMINATED INDOLES; ISOGRANULATIMIDE ANALOGS; POLYBROMINATED INDOLES; 1,3-DIBROMO-5,5-DIMETHYLHYDANTOIN; 2,3-DIBROMO-1-METHYLINDOLE; CARBAZOLES; LITHIATION; ALKALOIDS;

D O I：

10.1016/j.tetlet.2015.01.080

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Simple and efficient synthetic procedures for the selective preparation of 3-bromo/3-chloroindoles and 2,3-dibromo/2,3-dichloroindoles by using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) and 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) were developed. Using 1,4-dioxane as the solvent, a variety of indoles, treated with 0.55 equiv DBDMH/DCDMH, afford the corresponding 3-bromo/3-chloroindoles selectively in 82-99% yield. In 1,2-dichloroethane (DCE), a series of 2,3-dichloro/2,3-dibromoindoles were selectively obtained in 84-95% yield by treating with DBDMH/DCDMH. All the processes do not need extra catalysts, dry solvents, or harsh reaction conditions. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：1096 / 1098

页数：3

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