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Molecules 2010, 15(12), 8841-8855; doi:10.3390/molecules1512884
Article

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

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Received: 15 October 2010; in revised form: 25 November 2010 / Accepted: 30 November 2010 / Published: 3 December 2010
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Abstract: 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.
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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(12):8841-8855.

Chicago/Turabian Style

Najahi, Ennaji; Sudor, Jan; Chabchoub, Fakher; Nepveu, Françoise; Zribi, Fethi; Duval, Romain. 2010. "Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity." Molecules 15, no. 12: 8841-8855.


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