Bulletin of the Chemical Society of Japan · 1987 · 35 citations · 20 references
Natural SciencesChemistryCatalysisGreen ChemistryOrganic ChemistryCarbonyl ChemistryHeterocycle SynthesisHeterocyclic ChemistryOrganic SynthesisAlkylation ReactionsCarbonyl ReductionPyridine ChemistryPyridine SynthesisPyrrole ChemistryRegioselective CatalysisRegioselective Synthesis
Abstract A new method for the alkyl group introduction at the 3-position of pyridienes is described: Reductive disilylation of pyridine, its 2-methyl, 3-methyl, and 4-methyl derivatives affords the corresponding 1,4-disilyl-1,4-dihydropyridines. In the presence of a catalytic amount of tetrabutylammonium fluoride, these dihydropyridines smoothly react with a variety of aldehydes and ketones to give 3-alkylpyridines.
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