Alkylation of pyridine‐3,5‐dicarboxamide and pyridine‐3,5‐dicarbonitriles by radical substitution

Structural modification of NAD(P) model compounds, N,N,N',N' ‐tetramethylpyridine‐3,5‐dicarboxamide ( 1 ), pyridine‐3,5‐dicarbonitrile ( 2 ), and 4‐methylpyridine‐3,5‐dicarbonitrile ( 3 ), have been explored by the reaction with alkyl radicals such as the 1‐adamantyl, tert ‐butyl, and isopropyl radicals. The alkyl substitutions of compounds 1 , 2 , and 3 with the 1‐adamantyl and the tert ‐butyl radical gave both 2‐mono and 2,6‐disubstitution products, whereas the reaction of compound 2 with the isopropyl radical gave 2‐mono 6c , 2,4‐di 7c, 2,6‐di 8c , and 2,4,6‐trisubstitution 9c products.