Heterocycles in organic synthesis. Part 7. Synthesis of furfuryl derivatives via 2,4,6-trisubstituted pyridinium salts

Abstract

Nucleophilic displacement of the amino-group of furfurylamine by initial conversion into a 2,4,6-trisubstituted pyridinium perchlorate provides a convenient preparation of a wide variety of novel furfuryl derivatives. 2,4,6-Triphenylpyridinium derivatives are more reactive than their 2,4,6-trimethyl analogues. 2-(2,4,6-Triphenylpyridiniomethyl)furan is smoothly brominated in the 5-position, and the brominated product undergoes nucleophilic replacement of the pyridinio group with morpholine.