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 obta...
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| Format: | Article |
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MDPI AG
2010-12-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/15/12/8841/ |
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| author | Fethi Zribi Romain Duval Fakher Chabchoub Françoise Nepveu Ennaji Najahi Jan Sudor |
| author_facet | Fethi Zribi Romain Duval Fakher Chabchoub Françoise Nepveu Ennaji Najahi Jan Sudor |
| author_sort | Fethi Zribi |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-18T05:10:30Z |
| format | Article |
| id | doaj.art-b21500e3bf604470b7ab65484bc18760 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-18T05:10:30Z |
| publishDate | 2010-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-b21500e3bf604470b7ab65484bc187602022-12-21T21:19:54ZengMDPI AGMolecules1420-30492010-12-0115128841885510.3390/molecules1512884Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their ReactivityFethi ZribiRomain DuvalFakher ChabchoubFrançoise NepveuEnnaji NajahiJan SudorIn 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.http://www.mdpi.com/1420-3049/15/12/8841/2(1H)-pyrimidinones1,2,3-triazoles(3 + 2) cycloadditionalkynesazides |
| spellingShingle | Fethi Zribi Romain Duval Fakher Chabchoub Françoise Nepveu Ennaji Najahi Jan Sudor Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity Molecules 2(1H)-pyrimidinones 1,2,3-triazoles (3 + 2) cycloaddition alkynes azides |
| title | Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity |
| title_full | Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity |
| title_fullStr | Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity |
| title_full_unstemmed | Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity |
| title_short | Synthesis of 6-Amino-5-cyano-1,4-disubstituted-2(1H)-Pyrimidinones via Copper-(I)-catalyzed Alkyne-azide ‘Click Chemistry’ and Their Reactivity |
| title_sort | synthesis of 6 amino 5 cyano 1 4 disubstituted 2 1h pyrimidinones via copper i catalyzed alkyne azide click chemistry and their reactivity |
| topic | 2(1H)-pyrimidinones 1,2,3-triazoles (3 + 2) cycloaddition alkynes azides |
| url | http://www.mdpi.com/1420-3049/15/12/8841/ |
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