Transformations of 2,6-dimethyl- and 2,3-dimethyl-6-ethyl-4-(2′-furyl)pyridines involving the furan and pyridine rings

Alkyl-substituted 4-(2′-furyl)pyridines are brominated and nitrated in the C5' position of the furan ring; however, they do not undergo electrophilic substitution reactions such as acetylation, formylation, and chloro- and aminomethylation. Furyl-substituted indolizines and tetrahydropyridines were obtained from quaternary salts of 2,6-dimethyl-4-(2′-furyl)pyridine. © 1983 Plenum Publishing Corporation.