A series of pyranopyrazoles, namely, 7-(2-aminoethyl)-3,4-dimethyl-1-phenyl-1<em>H</em>-pyrazolo[3,4-b]pyridin-6(7<em>H</em>)-one (<strong>2</strong>), (<em>Z</em>)-3,4-dimethyl-1-(4-((4-nitrobenzylidene)amino)phenyl)pyrano[2,3-c]pyrazol-6(1<em>H</em>)-one (<strong>5</strong>), 1-(4-(3,4-dimethyl-6-oxopyrano[2,3-c]pyrazol-1(6<em>H</em>)-yl)phenyl)-3-(naphthalen-1-yl)urea (<strong>6</strong>), (<em>Z</em>)-ethyl 4-((3,4-dimethyl-6-oxo-1,6-dihydropyrano[2,3-c]pyrazol-5-yl)diazenyl)benzoate (<strong>8</strong>) and 3,4-dimethyl-<em>N</em>-(naphthalen-1-yl)-6-oxopyrano[2,3-c]pyrazole-1(6H)-carboxamide (<strong>9</strong>) were synthesized and characterized by means of their UV-VIS, FT-IR, ¹H-NMR and ¹³C-NMR spectral data. Density Functional Theory calculations of the synthesized pyranopyrazoles were performed using molecular structures with optimized geometries. Molecular orbital calculations have provided detail description of the orbitals, including spatial characteristics, nodal patterns, and the contributions of individual atoms.