HETEROCYCLES IN ORGANIC-SYNTHESIS .7. SYNTHESIS OF FURFURYL DERIVATIVES VIA 2,4,6-TRISUBSTITUTED PYRIDINIUM SALTS

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.