Abstract Pyridine-3-carboxamide (1) was reacted with alkyl radicals to give mono-, di-, and tri-alkylated products. The t-butyl radical gives only 6-t-butylpyridine-3-carboxamide (4a). The reactivity decreases in the order of t-butyl, isopropyl, and ethyl radicals. The product 4a reacts further with the 2-phthalimidoethyl radical to give 2-and 4-substituted products 9 and 10, which were transformed into tetrahydronaphthyridinone derivatives 11 and 12.
