Synthesis of 4-pyridines and 4--2,2'-bipyridines

Article abstract of DOI:10.1071/CH9951425

The synthesis is reported of 4-<ω-(3-thienyl)alkyl>pyridine (2), 4-<ω-(3-thienyl)alkyl>-2,2'-bipyridine (3) and 4-methyl-4'-<ω-(3-thienyl)alkyl>-2,2'-bipyridine (4), where the length of the alkyl chain is varied (n = 2, 5, 7, 9, 11).The synthetic methodology involved the reaction of the 3-(ω-bromoalkyl)thiophene with the anions derived from 4-methylpyridine, 4-methyl-2,2'-bipyridine or 4,4'-dimethyl-2,2'-bipyridine by lithiation.The n.m.r. (1H and 13C) and electronic spectral characteristics of the compounds are discussed.