[CMMIM][BF₄^–] Ionic Liquid-Catalyzed Facile, One-Pot Synthesis of Chromeno[4,3-d]pyrido[1,2-a]pyrimidin-6-ones: Evaluation of Their Photophysical Properties and Theoretical Calculations

Abstract

Herein, we have developed a novel synthetic route for the synthesis of chromeno [4,3-d]pyrido [1,2-a]pyrimidin-6-one derivatives 8a-q using an acid ionic liquid [CMMIM][BF 4− ] 4 via one-pot, three-component synthesis in aqueous ethanol at room temperature. A series of 17 derivatives have been successfully prepared with up to 93% yield. All the synthesized derivatives were well characterized using 1 H-NMR, 13 C-NMR, and FT-IR spectral techniques. Additionally, the photophysical properties of 12 selected derivatives including molar extinction coefficient (ε), Stokes shift (Δυ ̅ ), and quantum yield (Φ) varying from 0.52095 × 10 4 to 0.93248 × 10 4 , 4216 to 4668 cm −1 , and 0.0088 to 0.0459, respectively, have been determined. Furthermore, the experimental data are supported by density functional theory (DFT) and time-dependent DFT calculations. Theoretical investigations showed a trend similar to experimental results.

Synthesis, Structural Elucidation, In Silico and In Vitro Studies of New Class of Methylenedioxyphenyl-Based Amide Derivatives as Potential Myeloperoxidase Inhibitors for Cardiovascular Protection

“…A smaller global electrophilicity index implies a strong nucleophilic molecule, while a higher value denotes a strong electrophilic molecule. Molecules are classified as potent electrophiles if values are greater than 1.5 eV, moderate electrophiles if values range in between 0.8 and 1.5 eV, and minor electrophiles if the values are less than 0.8 eV. , The electrophilicity index value for MDC and ADC is larger than 1.5 eV, indicating that the molecules have a potent electrophilic nature that facilitates the formation of bonds with biomolecules. Molecules having greater HOMO–LUMO energy gap show lesser tendency for interaction and bond formation, while molecules with less HOMO–LUMO energy gap are more interactive and are more willing to participate in chemical events involving bond breaking or bond formation.…”

[CMMIM][BF4] as a Sustainable Catalyst for Spirooxindoles Synthesis via One‐Pot Multicomponent Reaction: Insights into their Photophysical Properties and Theoretical Calculations

“…We began the study by following a procedure for the synthesis of [CMMIM][BF 4 ] 4 as described by our research group [39] (Scheme 1). The obtained product was extensively investigated through 1 H, 13 C, DEPT-135 NMR, and FT-IR spectral approaches.…”

The Synthesis of Nitrogen- and Oxygen-Containing Heterocyclic Scaffolds Assisted by Ionic Liquids: A 2022 Literature Survey

“…Maiti and Pasuparthy reported the use of an acidic ionic liquid, 1-carboxymethyl-3-methyl imidazolium tetrafluoroborate [CMMIM][BF 4 – ], for the one-pot, three-component synthesis of chromeno[4,3- d ]pyrido[1,2- a ]pyrimidin-6-ones 127 (Scheme 41 ). 102 The IL [CMMIM][BF 4 – ] was synthesized using N -methylimidazole and chloroacetic acid followed by anion exchange using sodium tetrafluoroborate. Seventeen compounds were synthesized in moderate to high yields using this IL.…”