Three-Component Reaction of 4-Methylpyridine with Alkyl Propiolates and Secondary Phosphine Chalcogenides |
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Authors: | P?A?Volkov A?A?Telezhkin N?I?Ivanova K?O?Khrapova A?I?Albanov N?K?Gusarova Email author" target="_blank">B?A?TrofimovEmail author |
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Institution: | 1.Favorskii Irkutsk Institute of Chemistry, Siberian Branch,Russian Academy of Sciences,Irkutsk,Russia |
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Abstract: | The reaction between 4-methylpyridine, alkyl propiolates, and secondary phosphine oxides proceeded as N-vinylation-C-phosphorylation with stereo- and regioselective formation of (E)-N-ethenyl-C2- phosphoryl-1,2-dihydropyridines when using bis(2-phenylethyl)phosphine oxide] or (E)-N-ethenyl-C4- phosphoryl-1,4-dihydropyridines (when using diphenylphosphine oxide). The process occurred at 60–62°C within 3 h to give functional dihydropyridines in 40–82% yield. Under similar conditions, bis(2-phenylethyl) phosphine sulfide and selenide reacted with alkyl propiolates preferably by nucleophilic PH-monoaddition at the triple bond. |
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