Aldol condensation of 3-acetyl-1-(4-fluorophenyl)-5-phenyl-1H-pyrazole-4-carbonitrile with benzaldehyde afforded 1-(4-fluorophenyl)-5-phenyl-3-((E)-3-phenylacryloyl)-1H-pyrazole-4-carbonitrile, which in turn reacted with a series of 1,2-and 1,3-binucleophiles to afford new substituted pyrazoles, pyrimidines, and condensed azolopyrimidine derivatives attached to pyrazole scaffold at position 3. Moreover, multicomponent condensation reactions (MCRs) were used as an alternative method, and 1 H-13 C heteronuclear single quantum coherence (HSQC) in addition to heteronuclear multiple-bond correlation (HMBC) spectra were used for full confirmation of a selected example of these compounds. The reactivity of 1-(4-fluorophenyl)-5-phenyl-3-((E)-3-phenylacryloyl)-1H-pyrazole-4-carbonitrile towards active methylene derivatives, including malononitrile and ethyl cyanoacetate, was explored and afforded 2