Synthesis of new heterocyclic derivatives of retinoids

Reaction of α- and β-ionones 1 and 2 with dialkylformamide/phosphorus oxychloride affords enamines 6 and 7 along with the expected chloro derivatives 4 and 5 . Reaction of 6a with hydrazines, hydroxylamine and guanidine furnished pyrazoles, isoxazole, pyrimidine 8–10 showing the potential of these enaminones as key intermediates in the synthesis of synthetic retinoids.