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：

暂无

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.

引用

页码：5624 / 5630

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