The reductive alkylation of 3,4-disubstituted pyridines is reported using either sodium in ammonia or ammonia free conditions (Na, naphthalene, THF). This partial reduction process works cleanly and efficiently giving good yields of highly functionalised dihydropyridine templates. Radical cyclisation reactions were performed on these dihydropyridines and gave fused 2- and 3-ring heterocycles with defined stereochemistry.
