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

1
Laboratory of Applied Chemistry, Heterocycles, Fats and Polymers, Faculty of Science, University of Sfax, 3000 Sfax, Tunisia
2
Laboratory of Medicinal Chemistry of Natural Substances and Redox Pharmacophores, University of Toulouse, UPS, UMR 152, F-31062 Toulouse cedex 9, France
3
IRD, UMR 152, F-31062 Toulouse cedex 9, France
*
Author to whom correspondence should be addressed.
Molecules 2010, 15(12), 8841-8855; https://doi.org/10.3390/molecules1512884
Received: 15 October 2010 / Revised: 25 November 2010 / Accepted: 30 November 2010 / Published: 3 December 2010
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. View Full-Text
Keywords: 2(1H)-pyrimidinones; 1,2,3-triazoles; (3 + 2) cycloaddition; alkynes; azides 2(1H)-pyrimidinones; 1,2,3-triazoles; (3 + 2) cycloaddition; alkynes; azides
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Najahi, E.; Sudor, J.; Chabchoub, F.; Nepveu, F.; Zribi, F.; Duval, R. Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity. Molecules 2010, 15, 8841-8855.

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