Some Nucleophilic Addition Reactions of 2,5-Dihydropyridines: Synthesis of 2,3,6-Trialkyl(phenyl)-1,2,3,6-tetrahydropyridines and 2,3,6-Trialkyl(phenyl)pyridines

Article abstract of DOI:10.1021/jo00324a003

A series of 2,5-dialkyl(phenyl)-2,5-dihydropyridines (2) was prepared by reacting 1-lithio-2-alkyl(phenyl)-1,2-dihydropyridines (1) with alkyl halides.The 2,5-dihydropyridines (2) are stable when maintained cold under a nitrogen atmosphere, and these compounds react with alkyl(phenyl)lithium compounds by nucleophilic addition to the C=N moiety.The resultant products are 2,3,6-trialkyl(phenyl)-1,2,3,6-tetrahydropyridines (4) which can be oxidized (selenium) to the corresponding 2,3,6-trialkylpyridines (5).