Iron-catalyzed [3 + 2 + 1] annulation of 2-aminobenzimidazoles/3-aminopyrazoles and aromatic alkynes using N,N-dimethylaminoethanol as a one carbon synthon for the synthesis of pyrimido[1,2-a]benzimidazoles and pyrimido[1,2-b]indazoles

被引：0
|
作者：
Qin, Zemin [1 ,2 ,3 ]
Zhang, Ruiqin [2 ]
Ying, Shenpeng [1 ]
Ma, Yongmin [1 ,2 ]
机构：
[1] Taizhou Central Hospital, Taizhou University Hospital, Taizhou University, Zhejiang, Jiaojiang,318000, China
[2] Institute of Advanced Studies, School of Pharmaceutical Sciences, Taizhou University, Zhejiang, Jiaojiang,318000, China
[3] School of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou,310053, China
来源：
Organic Chemistry Frontiers | 2022年 / 9卷 / 20期
关键词：
3-aminopyrazole - Aminobenzimidazoles - Aromatic alkynes - Benzimidazoles - Indazole - Methine - Regio-selective - Simple++ - Synthons - Three-component;
D O I：
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中图分类号：
学科分类号：
摘要：
A simple and efficient method for the synthesis of pyrimido[1,2-a]benzimidazoles and pyrimido[1,2-b]indazoles from 2-aminobenzimidazoles/3-aminoindazoles, alkynes and N,N-dimethylaminoethanol by a three-component [3 + 2 + 1] annulation catalyzed by FeCl3 has been established, where N,N-dimethylaminoethanol was applied as a methine source. Good tolerance of the reaction makes this method applicable to construct biologically active pyrimido[1,2-a]benzimidazoles and pyrimido[1,2-b]indazoles. In addition, regioselective aryl substituted pyrimido[1,2-a]benzimidazoles were synthesized in the presence of TfOH. Replacement of alkynes with acetaldehydes gave the same pyrimido[1,2-a]benzimidazoles and pyrimido[1,2-b]indazoles. © 2022 The Royal Society of Chemistry.
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页码：5624 / 5630
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