期刊
TETRAHEDRON
卷 120, 期 -, 页码 -出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2022.132856
关键词
3-triazoles; enaminones; 3-dipolar cycloadditions; Aryl azides; Hammett correlation
资金
- Coordenacao de Aperfeicoamento de Pessoal de Nivel Superior - Brazil (CAPES) [001]
- CNPq
- Carlos Chagas Filho Foundation for Research Support of the State of Rio de Janeiro (Fundacao Carlos Chagas Filho de Amparo a Pesquisa do Estado do Rio de Janeiro
- FAPERJ)
This study reports the synthesis of new 4-acyl-1,2,3-triazoles through metal-free and solvent-free cycloaddition reactions, achieving high yields. The reaction mechanism for the synthesis of 4-acyl-1,2,3-triazoles was proposed based on experimental and theoretical data.
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.
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