Reaction of α- and β-ionones I and II with dialkylformamide/phosphorus oxychloride affords enamines III (R = Me2N, Et2N) and IV (R = Me2N) along with the expected chloro derivs. III and IV (R = Cl). Reaction of III (R = Me2N) with hydrazines, hydroxylamine and guanidine furnished pyrazole, isoxazole, pyrimidine derivs., e.g. V, showing the potential of these enaminones as key intermediates in the synthesis of synthetic retinoids.
Synthesis of new heterocyclic derivatives of retinoids
ANZALDI, MARIA;BALBI, ALESSANDRO
1998-01-01
Abstract
Reaction of α- and β-ionones I and II with dialkylformamide/phosphorus oxychloride affords enamines III (R = Me2N, Et2N) and IV (R = Me2N) along with the expected chloro derivs. III and IV (R = Cl). Reaction of III (R = Me2N) with hydrazines, hydroxylamine and guanidine furnished pyrazole, isoxazole, pyrimidine derivs., e.g. V, showing the potential of these enaminones as key intermediates in the synthesis of synthetic retinoids.
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