The Solid-State Michael Addition of 3-Methyl-1-phenyl-5-pyrazolone

Article abstract of DOI:10.1002/jhet.5570350124

A novel solid-state Michael addition between pyrazolone 1 and 4-arylidenepyrazolones 2 at ambient temperature produced Michael adducts, 4,4′-arylidenebis(3-methyl-1-phenyl-5-pyrazolones) 3. Pyrazolones 3 formed salts 4 with Cu²⁺ in solution, indicating the enolic structure of the pyrazolone rings. The reactivity of 2 with 1 is discussed in terms of the electronic and steric effects of the substituent on the arylidene group of compounds 2. Pyrazolone 1 also underwent the solid state Michael addition reaction with maleimide at 100° to give the adducts 7, 8 and 9.