synthesis of 6-amino-5-cyano-1,4-disubstituted-2(1h)-pyrimidinones via copper-(i)-catalyzed alkyne-azide ‘click chemistry’ and their reactivity合成6-amino-5-cyano-1 4-disubstituted-2(1 h)-pyrimidinones通过铜-(i)催化alkyne-azideu201c点击化学u201d和他们的反应.pdf

Molecules 2010, 15, 8841-8855; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)- Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity Ennaji Najahi 1,2, Jan Sudor 2,3, Fakher Chabchoub 1, Françoise Nepveu 2,3,*, Fethi Zribi 1 and , 2 3 Romain Duval 1 Laboratory of Applied Chemistry, Heterocycles, Fats and Polymers, Faculty of Science, University of Sfax, 3000 Sfax, Tunisia; E-Mails: najahimco@yahoo.fr (E.N.); fakher.chabchoub@yahoo.fr (F.C.); zfnfethi@yahoo.fr (F.Z.) 2 Laboratory of Medicinal Chemistry of Natural Substances and Redox Pharmacophores, University of Toulouse, UPS, UMR 152, F-31062 Toulouse cedex 9, France; E-Mails: sudor@cict.fr (J.S.); romain@cict.fr (R.D.) 3 IRD, UMR 152, F-31062 Toulouse cedex 9, France * Author to whom correspondence should be addressed; E-Mail nepveu@cict.fr; Tel.: +33562256869; Fax +3362259804. Received: 15 October 2010; in revised form: 25 November 2010 / Accepted: 30 November 2010 / Published: 3 December 2010 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-cyan