Urea-based ternary deep eutectic solvent: design, theoretical study, and application in the synthesis of 3,4-dihydropyrimidinones

کد مقاله : 1202-ICOC

نویسندگان

احسان احمدی احمدآبادی *، فاطمه تمدن، محمدرضا نوربالا دانشگاه یزد

چکیده مقاله

Deep eutectic solvents (DESs) are biodegradable, low-cost, and green alternatives to volatile organic solvents, ionic liquids, and expensive metal catalysts [1,2]. DESs are formed by mixing hydrogen-bond donors (HBDs) and acceptors (HBAs) in specific molar ratios and exhibit significant melting point depression due to charge delocalization and extensive hydrogen-bonding networks [2]. Their advantages of easy preparation, atom economy, tunability, non-flammability, and strong solvating power have led to the development of various types, including magnetic, hydrophilic, hydrophobic, natural, and ternary DESs (TDESs) [3,4]. TDESs, prepared from three solid precursors, represent the latest class with enhanced properties for specialized applications. In this study, a novel urea-based TDES was designed, synthesized, and characterized using FT-IR, TGA, phase diagram, density/viscosity measurements, DFT geometry optimization, and electrostatic potential surface (EPS) analysis. DFT calculations revealed non-covalent donor-acceptor interactions responsible for melting point depression and stability, while EPS mapping illustrated 3D charge distribution, nucleophilic/electrophilic sites, and hydrogen-bonding regions explaining the TDES’s superior polarity, viscosity, and reactivity. This multifunctional TDES simultaneously acted as solvent, Lewis acid catalyst, and a component in a rapid, one-pot, 3-component condensation of ethyl acetoacetate with aromatic aldehydes to affording 3,4-dihydropyrimidinones in excellent yields and purities (Scheme 1).

کلیدواژه ها

Ternary deep eutectic solvent, Theoretical study, 3,4-dihydropyrimidinones,

وضعیت: پذیرفته شده