1,3-Dipolar cycloaddition reactions of enaminones and azides: Synthesis of 4-acyl-1,2,3-triazoles and mechanistic studies

被引：7

作者：

Gaspar, Francisco V. ^{[1
]}

Azevedo, Marcelo F. M. F. ^{[1
]}

Carneiro, Leonardo S. A. ^{[1
]}

Ribeiro, Samuel B. ^{[1
]}

Esteves, Pierre M. ^{[2
]}

Buarque, Camilla D. ^{[1
]}

机构：

[1] Pontifical Catholic Univ Rio De Janeiro PUC Rio, Dept Chem, Rua Marque s Sa Vicente 225, BR-20551031 Rio De Janeiro, RJ, Brazil

[2] Univ Fed Rio De Janeiro UFRJ, Inst Quim, Ave Athos Silveira Ramos 149,Bl A 622, BR-21941909 Rio De Janeiro, RJ, Brazil

来源：

TETRAHEDRON | 2022年 / 120卷

关键词：

3-triazoles; enaminones; 3-dipolar cycloadditions; Aryl azides; Hammett correlation; AZIDOPHENYL ARYLSELENIDES; ORGANOCATALYTIC SYNTHESIS; REGIOSPECIFIC SYNTHESIS; 1,2,3-TRIAZOLES; CASCADE; KETONES; ACCESS;

D O I：

10.1016/j.tet.2022.132856

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

4-acyl-1,2,3-triazoles are an important and versatile chemical scaffold widely applied in medicinal chemists due to their interesting pharmacological properties. Acknowledging the constant need for a greener, simple and scalable methodology in medicinal chemistry, herein we report the synthesis of new 4-acyl-1,2,3-triazoles through the metal-free and solvent-free cycloaddition reactions between enami-nones and aryl azides, obtaining yields of 41-77%. Based on experimental Hammett correlation and theoretical Quantum calculations data a reaction mechanism for 3-dipolar cycloadditions synthesis of 4-acyl-1,2,3-triazoles was proposed. (c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：11

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