Synthesis of pyridine and pyrimidine derivatives by reaction of pyrylium salts with ureas, thioureas, and isothioureas

Abstract

2,4,6-Triphenylpyrylium perchlorate is converted to 2,4,6-triphenylpyridine in reactions with urea and N-acetyl- and N,N-dimethylureas, whereas it is converted to 1,2,4,6-tetraphenylpyridinium perchlorate on reaction with N,N′-diphenylurea. The reaction of pyrylium perchlorates with thiosemicarbazide and semicarbazide leads to 1-thiocarbamido- and 1-carbamidopyridinium salts. The latter reacts with 2,4,6-triphenylpyrylium perchlorate to give 1-aminopyridinium salts, which were acylated with acetic anhydride. Difficult-to-obtain 2-alkylthio-4,6-diarylpyrimidines were synthesized in 40–93% yields by the reaction of 2,4,6-triarylpyrylium salts with S-alkylisothioureas.