Synthesis, spectral analysis, quantum studies, NLO, and thermodynamic properties of the novel 5-(6-hydroxy-4-methoxy-1-benzofuran-5-ylcarbonyl)-6-amino-3-methyl-1H-pyrazolo[3,4-b] pyridine (HMBPP).

Ring opening followed by ring closure reactions of 4-methoxy-5-oxo-5H-furo[3,2-g] chromene-6-carbonitrile (1) with 5-amino-3-methyl-1H-pyrazole (2) afforded the novel 5-(6-hydroxy-4-methoxy-1-benzofuran-5-ylcarbonyl)-6-amino-3-methyl-1H-pyrazolo[3,4-b] pyridine (3, HMBPP). The chemical structure of the synthesized compound was established based on elemental analysis and spectral data. The chemical calculations were performed using the Becke3-Lee-Yang-Parr (B3LYP) and Coulomb Attenuating Method (CAM-B3LYP)/6-311++G(d,p) basis sets at the DFT level of theory. The Coulomb-attenuating method (CAM-B3LYP) and Corrected Linear Response Polarizable Continuum Model (CLR) PCM were used to obtain the theoretical electronic absorption spectra in the gas phase, methanol, and cyclohexane, respectively, indicating good agreement with the observed spectra. The local reactivity descriptors supported the high reactivity of C7 for nucleophilic attack. The computed total energy and thermodynamic parameters at the same level of calculations confirmed the high stability of structure 3 (HMBPP) as compared with the other expected structure 4. The (1)H and (13)C chemical shift values, as well as vibrational wavenumber values, were theoretically determined and exhibited a high correlation with the experimental data. Natural bond orbital analysis (NBO) was used to investigate hyper conjugative interactions. The first static hyperpolarizability, second hyperpolarizability, polarizability, and electric dipole moment have been determined. At different temperatures, the thermodynamic properties of the compounds were calculated.