Vinylation of α-Aminoazoles with Triethylamine: A General Strategy to Construct Azolo[1,5-a]pyrimidines with a Nonsubstituted Ethylidene Fragment

被引：26

作者：

Gao, Qinghe ^{[1
]}

Sun, Zhenhua ^{[1
]}

Xia, Qinfei ^{[2
]}

Li, Ruonan ^{[1
]}

Wang, Wenlong ^{[1
]}

Ma, Siwei ^{[1
]}

Chai, Yixin ^{[1
]}

Wu, Manman ^{[1
]}

Hu, Wei ^{[2
]}

Abranyi-Balogh, Peter ^{[3
]}

Keseru, Gyorgy M. ^{[3
]}

Han, Xinya ^{[2
]}

机构：

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

[2] Anhui Univ Technol, Sch Chem & Chem Engn, Maanshan 243002, Anhui, Peoples R China

[3] Res Ctr Nat Sci, Med Chem Res Grp, H-1117 Budapest, Hungary

来源：

ORGANIC LETTERS | 2021年 / 23卷 / 07期

基金：

国家重点研发计划;

关键词：

C-H ACTIVATION/ANNULATION;

D O I：

10.1021/acs.orglett.1c00571

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new general synthesis of pharmaceutically important azolo[1,5-a]pyrimidines starting from widely available 3(5)-aminoazoles, aldehydes, and triethylamine is developed. The key is to enable the vinylation reaction that allows the in situ generation of elusive acyclic enamines and the subsequent annulation reaction to occur. This direct and practical strategy is capable of constructing a range of 5,6-unsubstituted pyrazolo[1,5-a]pyrimidines and [1,2,4]triazolo[1,5-a]pyrimidines. More importantly, this protocol provides a concise synthetic route to prepare the clinically used zaleplon.

引用

页码：2664 / 2669

页数：6

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