Abstract. Novel 4,4 ′- ( arylmethylene ) - bis(3 - methyl -1- phenyl-1H-pyrazol - 5 - ol) derivative 2 was synthesized via interaction of N - ( 4 - chlorophenyl ) - 2 - (4 - formylphenoxy) acetamide (1) with diverse available reagent (two mole from 3 - methyl -1H -pyrazol - 5(4 H) -one). Moreover, One - pot pseudo three-component reaction of hydrazine hydrate, ethyl acetoacetate and aldehydes in ethanole using pipridine at 70°C afforded the corresponding aminopyrazole derivative 3. on the other hand, cyanoacetamide scaffolds 4a,b was reacted with aromatic aldehyde particularly N -( 4 -chlorophenyl ) - 2 - (4 -formylphenoxy) acetamide (1), to afford arylidenes 5 a, b that undergoes cyclization by heating in ethanol containing drops of piperidine as catalyst, and malononitrile afforded the corresponding pyridinone derivatives 6 a,b. All freshly synthesized scaffolds were elucidated by considering the data of both elemental and spectral analyses.