Cj. Valduga et al., REACTIVITY OF P-PHENYL SUBSTITUTED BETA-ENAMINO COMPOUNDS USING K-10 ULTRASOUND - I - SYNTHESIS OF PYRAZOLES AND PYRAZOLINONES/, Journal of heterocyclic chemistry, 35(1), 1998, pp. 189-192
The reactivity of the beta-enamino ketones, 3-amino-1-(p-phenyl-substi
tuted)-2-buten-1-ones 1a-d and beta-enamino esters. hyl-3-amino-3-(p-p
henyl-substituted)-2-propenoates 5a-d were evaluated by systematic stu
dies of the reactions with hydrazine and methylhydrazine by reactions
with solid support K-10/ultrasound and homogeneous media (reflux in et
hanol or dichloromethane) yielding pyrazole rings 2a-d, N-methylpyrazo
les 3a-d, 4a-d and N-methylpyrazolinones 6a-c and 7a-c. The regiochemi
stry of the cyclization showed dependence of the reaction conditions e
mployed as well as the substituent in the aromatic ring.