Isocyanide addition to pyridinium salts. Efficient entry into substituted nicotinonitrile derivatives |
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Authors: | Williams Nana Aba O Masdeu Carme Díaz José Luis Lavilla Rodolfo |
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Affiliation: | Institute for Research in Biomedicine, Barcelona Science Park, Josep Samitier 1-5, 08028 Barcelona, Spain. |
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Abstract: | The addition of isocyanides to pyridinium salts is studied. The process takes place efficiently when a carboxamido group is present in the 3 position of the pyridine ring. The outcome of the reaction involves the stabilization of the nitrilium intermediate by the amide, which suffers a mild dehydration, leading regioselectively to beta-cyano-gamma-carbamoyl-1,4-dihydropyridines. In this way, a variety of nicotinamide derivatives were carbamoylated. Extension to quinolinium, isoquinolinium, and N-acylpyridinium salts is also reported. [reaction: see text] |
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