Bronsted acid-promoted ring-opening and annulation of thioamides and 2H-azirines to synthesize 2,4,5-trisubstituted thiazoles

被引：4

作者：

Wang, Meng ^{[1
]}

Ma, Jingyi ^{[1
]}

Wang, Hesong ^{[1
]}

Hu, Fangpeng ^{[1
]}

Sun, Bo ^{[1
]}

Tan, Taiyan ^{[1
]}

Li, Minglang ^{[1
]}

Huang, Guosheng ^{[1
]}

机构：

[1] Lanzhou Univ, Dept Chem, State Key Lab Appl Organ Chem, Key Lab Nonferrous Met Chem & Resources Utilizat G, Lanzhou 730000, Peoples R China

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 27期

关键词：

CYCLOADDITION; CHEMISTRY;

D O I：

10.1039/d3ob00245d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In this study, a metal-free synthesis of 2,4,5-trisubstituted thiazoles using 2H-azirines and thioamides is disclosed. Under the catalysis of HClO4, the protocol was realized through a novel chemical bond breaking of 2H-azirine, which is usually achieved using a metal catalyst. It provides an efficient and green route for the synthesis of substituted thiazoles with a broad substrate scope. Preliminary mechanistic studies show that such a reaction may involve a ring-opening reaction, annulation, and a hydrogen atom rearrangement process.

引用

页码：5532 / 5536

页数：5

共 35 条

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