Experimental, spectroscopic, thermodynamic, and DFT study of a novel cyanomethylchrome nopyridinecarbonitrile (CCPC)

A novel heterocyclic system, 5-cyanomethylchromeno[4,3-b]pyridine-3-carbonitrile (CCPC, 3), was synthesized via the reaction of 3-(6,8-dimethylchromonyl)acrylonitrile (1) with cyanoacetamide (2) under basic conditions. The transformation proceeds through a cascade mechanism involving Michael addition, γ-pyrone ring opening, and double recyclization. The structure of CCPC was confirmed by analytical and spectral data. Density functional theory (DFT/B3LYP/6-311 + + G(d, p)) was used to optimize its molecular geometry and investigate electronic properties, global reactivity descriptors, molecular electrostatic potential, and intramolecular charge transfer characteristics. Thermokinetic behavior was evaluated using KiSThelP, while UV–Vis spectra were simulated via TDDFT, showing solvent-dependent absorption shifts. SwissADME analysis indicated favorable drug-likeness according to Lipinski’s and Veber’s rules. Overall, the combined experimental and computational study provides insight into the structure, reactivity, stability, and potential applications of CCPC.