Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity

Molecules

Ennaji Najahi¹  Jan Sudor¹  Fakher Chabchoub¹  Françoise Nepveu¹  Fethi Zribi¹ 

[1] ¹Laboratory of Applied Chemistry, Heterocycles, Fats and Polymers, Faculty of Science, University of Sfax, 3000 Sfax, Tunisia ²Laboratory of Medicinal Chemistry of Natural Substances and Redox Pharmacophores, University of Toulouse, UPS, UMR 152, F-31062 Toulouse cedex 9, France ³IRD, UMR 152, F-31062 Toulouse cedex 9, France

关键词: 2(1H)-pyrimidinones;    1;    2;    3-triazoles;    (3 + 2) cycloaddition;    alkynes;    azides;   

DOI  :  10.3390/molecules1512884

来源: mdpi

【 摘 要 】

In this paper we present the room temperature synthesis of a novel serie of 1,4-disubstituted-1,2,3-triazoles 4a-l by employing the (3 + 2) cycloaddition reaction of pyrimidinones containing alkyne functions with different model azides in the presence of copper sulphate and sodium ascorbate. To obtain the final triazoles, we also synthesized the major precursors 6-amino-5-cyano-1,4-disubstituted-2(1H)-pyrimidinones 3a-r from ethyl 2,2-dicyanovinylcarbamate derivatives 2a-c and various primary aromatic amines containing an alkyne group. The triazoles were prepared in good to very good yields.

【 授权许可】

CC BY   
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.