Potassium Carbonate–Mediated Efficient and Convenient Synthesis of 3-Methyl-1-phenylchromeno[4,3-<i>c</i>]pyrazol-4(1<i>H</i>)-ones

Grover, Jagdeep; Roy, Somendu Kumar; Jachak, Sanjay M.

doi:10.1080/00397911.2013.879184

Cited by 9 publications

(3 citation statements)

References 28 publications

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“…Afterward, the functionalization of 3-acetyl-coumarin derivatives 1a-d with phenylhydrazine was performed through acid catalysis with glacial acetic acid to obtain compounds 2a-d (Scheme 1). The experimental yields are in the 65-74% range, according to precise reports about the synthesis of the same compounds [2,29,32,45]. The H-4 signal in the 1 H NMR spectra indicated the formation of compounds 1a-d (Figures S1-S8), appearing in the 8.40-8.67 ppm range [31].…”

Section: Synthesis and Structural Characterizationsupporting

confidence: 60%

Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Villa-Martínez

Magaña-Vergara²,

Rodríguez³

et al. 2022

Molecules

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Intramolecular charge transfer (ICT) effects are responsible for the photoluminescent properties of coumarins. Hence, optical properties with different applications can be obtained by ICT modulation. Herein, four 3-acetyl-2H-chromen-2-ones (1a–d) and their corresponding fluorescent hybrids 3- (phenylhydrazone)-chromen-2-ones (2a–d) were synthesized in 74–65% yields. The UV-Vis data were in the 295–428 nm range. The emission depends on the substituent in position C-7 bearing electron-donating groups. Compounds 1b–d showed good optical properties due to the D-π-A structural arrangement. In compounds 2a–d, there is a quenching effect of fluorescence in solution. However, in the solid, an increase is shown due to an aggregation-induced emission (AIE) effect given by the rotational restraints and stacking in the crystal. Computational calculations of the HOMO-LUMO orbitals indicate high absorbance and emission values of the molecules, and gap values represent the bathochromic effect and the electronic efficiency of the compounds. Compounds 1a–d and 2a–d are good candidates for optical applications, such as OLEDs, organic solar cells, or fluorescence markers.

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Section: Synthesis and Structural Characterizationsupporting

confidence: 60%

Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Villa-Martínez

Magaña-Vergara²,

Rodríguez³

et al. 2022

Molecules

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“…In continuation, different bases were scrutinized for the solvent-free cyclization of CO 2 and 1a at 100 °C, 20 bar CO 2 pressure for 12 h, and the results are listed in Table . Experimental results suggested that the catalytic performance was remarkably affected toward the selective formation of 2a , with different alkali and alkaline earth metal carbonates, namely Na 2 CO 3 , K 2 CO 3 , CaCO 3 , and Cs 2 CO 3 . Notably, using 10 wt % of CoMgCe catalyst and 3 mmol of DMAB as the reductant, the reaction did not proceed in the absence of base (Table , entry 1).…”

Section: Resultsmentioning

confidence: 99%

“…Experimental results suggested that the catalytic performance was remarkably affected toward the selective formation of 2a, with different alkali and alkaline earth metal carbonates, namely Na 2 CO 3 , K 2 CO 3 , CaCO 3 , and Cs 2 CO 3 . 72 Notably, using 10 wt % of CoMgCe catalyst and 3 mmol of DMAB as the reductant, the reaction did not proceed in the absence of base (Table 3, entry 1). In accordance with previous literature reports, K 2 CO 3 as the base provided the highest yield of product 2a, among the other carbonates listed (Table 3, entry 3).…”

Section: Optimization Of Reaction Parametersmentioning

confidence: 99%

Stable Engineered Trimetallic Oxide Scaffold as a Catalyst for Enhanced Solvent-Free Conversion of CO₂ into Value-Added Products

et al. 2023

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This work demonstrates the development of mesoporous trimetallic oxide scaffolds (TOSs) as heterogeneous catalysts for the solvent-free transformation of CO2 into various value-added products. The TOS catalyst was prepared using a solution-combustion protocol as a time- and energy-saving method using cobalt, magnesium, and cerium metal nitrate salts as precursors and ethylene glycol as the fuel system and compared with their monometallic counterparts. Characterization suggested strong metal–metal and metal–oxygen interactions in the 3D-interconnected hierarchical porous network, which resulted in substantial alteration in the electronic, structural, and physicochemical properties. This resulted in an appreciable surface area, acid–base cooperative sites, and a larger pore volume in the catalyst. Thereafter, the CoMgCe-TOS catalyst was first used for the solvent-free cyclization of o-phenylenediamines and CO2 to produce benzimidazoles. In the presence of dimethylamine borane as a reductant, benzimidazoles were obtained in 94% yield at 100 °C under pressurized conditions, along with good recyclability for 12 cycles. It was established that selectivity toward benzimidazole improved upon the incorporation of basic metals (Mg and Ce), with Co aiding in the formation of cooperative Lewis acid–base sites. A plausible mechanism was also predicted, wherein the overall conversion of reactants for the N-formylation step was influenced by the number and strength of basic sites, and the cyclization step for selectively obtaining benzimidazole was affected by the acidic site strength. Besides the production of benzimidazole, the catalyst was also highly active for the synthesis of cyclic carbonates using epoxides and CO2 under optimized reaction conditions. This work therefore provides a new and greener route for the synthesis of benzimidazoles and organic carbonates, which can be easily adapted for scale-up applications.

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ChemInform Abstract: Potassium Carbonate‐Mediated Efficient and Convenient Synthesis of 3‐Methyl‐1‐phenylchromeno[4,3‐c]pyrazol‐4(1H)‐ones.

2014

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Potassium Carbonate–Mediated Efficient and Convenient Synthesis of 3-Methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones

Cited by 9 publications

References 28 publications

Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Stable Engineered Trimetallic Oxide Scaffold as a Catalyst for Enhanced Solvent-Free Conversion of CO₂ into Value-Added Products

ChemInform Abstract: Potassium Carbonate‐Mediated Efficient and Convenient Synthesis of 3‐Methyl‐1‐phenylchromeno[4,3‐c]pyrazol‐4(1H)‐ones.

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Potassium Carbonate–Mediated Efficient and Convenient Synthesis of 3-Methyl-1-phenylchromeno[4,3-c]pyrazol-4(1H)-ones

Cited by 9 publications

References 28 publications

Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Synthesis, Optical Characterization in Solution and Solid-State, and DFT Calculations of 3-Acetyl and 3-(1′-(2′-Phenylhydrazono)ethyl)-coumarin-(7)-substituted Derivatives

Stable Engineered Trimetallic Oxide Scaffold as a Catalyst for Enhanced Solvent-Free Conversion of CO2 into Value-Added Products

ChemInform Abstract: Potassium Carbonate‐Mediated Efficient and Convenient Synthesis of 3‐Methyl‐1‐phenylchromeno[4,3‐c]pyrazol‐4(1H)‐ones.

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Stable Engineered Trimetallic Oxide Scaffold as a Catalyst for Enhanced Solvent-Free Conversion of CO₂ into Value-Added Products