Synthesis of 6-amino-5-cyano-1,4-disubstituted-2(1H)-pyrimidinones via copper-(I)-catalyzed alkyne-azide 'click chemistry' and their reactivity.
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.
Laboratory of Applied Chemistry, Heterocycles, Fats and Polymers, Faculty of Science, University of Sfax, 3000 Sfax, Tunisia. najahimco@yahoo.fr
Ennaji
E
Najahi
Jan
J
Sudor
Fakher
F
Chabchoub
Françoise
F
Nepveu
Fethi
F
Zribi
Romain
R
Duval
D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D011744:Pyrimidinones / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000138:chemical synthesis / Q000737:chemistry
D000480:Alkynes; D011744:Pyrimidinones; D014230:Triazoles; D003300:Copper