DMSO/SOCl2-Enabled Synthesis of 3-Chloroindoles via Desulfonylative Chlorocyclization of N,N-Disubstituted 2-Alkynylanilines

被引：3
|
作者：
Li, Xuemin [1 ]
Cheng, Yifu [1 ]
Li, Yue [2 ]
Sun, Fengxia [3 ,4 ]
Zhan, Xiangyu [1 ]
Yang, Zhifang [1 ]
Yang, Jingyue [2 ]
Du, Yunfei [1 ]
机构：
[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin Key Lab Modern Drug Delivery & High Effici, Tianjin 300072, Peoples R China
[2] Yanshan Univ, Hebei Key Lab State Key Lab Metastable Mat Sci & T, Qinhuangdao 066004, Peoples R China
[3] Hebei Univ Sci & Technol, Res Ctr Chem Safety & Secur & Verificat Technol, Shijiazhuang 050018, Peoples R China
[4] Hebei Univ Sci & Technol, Coll Chem & Pharmaceut Engn, Shijiazhuang 050018, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 03期
基金：
中国国家自然科学基金;
关键词：
INTRAMOLECULAR IPSO-HALOCYCLIZATION; EFFICIENT SYNTHESIS; DIMETHYL-SULFOXIDE; C-N; INDOLE; HALOGENATION; DERIVATIVES; CYCLIZATION; ALKYNES; ACIDS;
D O I：
10.1021/acs.joc.3c02471
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The application of the DMSO/SOCl2 system enabled the intramolecular cyclization/chlorination of N,N-disubstituted 2-alkynylanilines, leading to the synthesis of a series of 3-chloroindoles with moderate to good yields. Differing from the previously reported interrupted Pummerer reaction featuring the introduction of SMe moiety, the current approach adopted an alternative pathway that realized the incorporation of chlorine atom to the indole skeleton via a desulfonylative chlorocyclization process.
引用
收藏
页码：2039 / 2049
页数：11
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