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Utilization of 2-ethoxymethylene-3-oxobutanenitrile in the synthesis of heterocycles possessing biological activity |
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| Authors: | Petra ?ernuchová ,Giang Vo-Thanh,André Loupy,Soňa Jantová |
| Affiliation: | a Department of Organic Chemistry, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic b Laboratory of Selective Reactions on Supports, ICMMO, CNRS UMR 8615, Building 410, Paris-South University, 914 05 Orsay-Cedex, France c Department of Biochemistry and Microbiology, Faculty of Chemical and Food Technology, Slovak Technical University, Radlinského 9, SK-812 37 Bratislava, Slovak Republic |
| Abstract: | 2-Ethoxymethylene-3-oxobutanenitrile is a versatile trifunctional reagent that allows the introduction of a three-carbon moiety to amine-substrates. The reaction of the title compound with hydrazines has been studied leading to appropriate substituted pyrazoles 4-11. Reactions with other dinitrogen nucleophiles were studied giving access to a set of fused pyrimidines 13. All types of compounds displayed biological activity against bacteria, filamentous fungi and tumour HeLa cells, but not for yeasts. Pyrazole 10 and pyrimidine 13d have been found to possess the broadest activity. |
| Keywords: | Pyrazoles Pyrimidines Biological activity Aminobenzothiazole Aminobenzimidazole |
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