One-pot three-component reaction of 3-(polyfluoroacyl)chromones with active methylene compounds and ammonium acetate: regioselective synthesis of novel R-containing nicotinic acid derivatives |
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| Authors: | Vyacheslav Ya. Sosnovskikh Roman A. Irgashev |
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| Affiliation: | a Department of Chemistry, Ural State University, 620083 Ekaterinburg, Russian Federation
b Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 620041 Ekaterinburg, Russian Federation |
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| Abstract: | Reactions of 3-(polyfluoroacyl)chromones with acetoacetamide and ethyl acetoacetate in the presence of ammonium acetate proceed at the C-2 atom of the chromone system with pyrone ring-opening and subsequent cyclization to 5-salicyloyl-2-methyl-6-(trifluoromethyl)nicotinamides, ethyl 5-salicyloyl-2-methyl-6-(trifluoromethyl)nicotinates, and ethyl 5-hydroxy-2-methyl-5-(polyfluoroalkyl)-5H-chromeno[4,3-b]pyridine-3-carboxylates. Similar reaction with β-aminocrotononitrile gave 5-hydroxy-2-methyl-5-(polyfluoroalkyl)-5H-chromeno[4,3-b]pyridine-3-carbonitriles. |
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| Keywords: | Three-component reactions 3-(Polyfluoroacyl)chromones Active methylene compounds Ammonium acetate Nicotinic acid derivatives |
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