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. 2010 Dec 3;15(12):8841-55.
doi: 10.3390/molecules1512884.

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 , Jan Sudor, Fakher Chabchoub, Françoise Nepveu, Fethi Zribi, Romain Duval
Affiliations

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 et al. Molecules. .

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.

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Figures

Scheme 1
Scheme 1
Synthesis of 6-amino-5-cyano-1,4-disubstituted-2(1H)-pyrimidinones (3a-r). Reagents and conditions: (i) primary aromatic amines, chlorobenzene, 110 °C, (2~4) h.
Scheme 2
Scheme 2
Synthesis of 1,4-disubstituted-1,2,3-triazoles 4a-l. Reagents and conditions: (a) Na-ascorbate (0.45 equiv), CuSO4·5H2O (0.1 equiv), THF/H2O/t-BuOH (3:1:1, v/v/v), rt, 2d.
Figure 1
Figure 1
Structures of the three different azides used in this work.
Figure 2
Figure 2
X-ray crystal analysis of compound 3b.
Figure 3
Figure 3
X-ray crystal analysis of compound 3g.
See this image and copyright information in PMC

References

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