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Application of Deep Eutectic Solvents in the Synthesis of Substituted 2-Mercaptoquinazolin-4(3H)-Ones: A Comparison of Selected Green Chemistry Methods.

ABSTRACT: In this study, deep eutectic solvents (DESs) were used as green and eco-friendly media for the synthesis of substituted 2-mercaptoquinazolin-4(3H)-ones from different anthranilic acids and aliphatic or aromatic isothiocyanates. A model reaction on anthranilic acid and phenyl isothiocyanate was performed in 20 choline chloride-based DESs at 80 °C to find the best solvent. Based on the product yield, choline chloride:urea (1:2) DES was found to be the most effective, while DESs acted both as solvents and catalysts. Desired compounds were prepared with moderate to good yields using stirring, microwave-assisted, and ultrasound-assisted synthesis. Significantly, higher yields were obtained with mixing and ultrasonication (16-76%), while microwave-induced synthesis showed lower effectiveness (13-49%). The specific contribution of this research is the use of DESs in combination with the above-mentioned green techniques for the synthesis of a wide range of derivatives. The structures of the synthesized compounds were confirmed by ¹H and ¹³C NMR spectroscopy.

SUBMITTER: Komar M

PROVIDER: S-EPMC8780518 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:The Artemisia argyi leaf (AL) has been used as a traditional medicine and food supplement in China and other Asian countries for hundreds of years. Phytochemical studies disclosed that AL contains various bioactive constituents. Among bioactive constituents, phenolic acids have been recognized as the main active compounds in AL. To the best of our knowledge, no research has been focused on extraction method for the bioactive phenolic acids from AL. Nowadays, deep eutectic solvents (DESs) are emerging as a new type of green and sustainable solvent for efficient extraction of bioactive compounds from natural products. In the present study, an environmentally friendly extraction method based on DESs was established to extract bioactive phenolic acids from ALs. Diverse tailor-made solvents, including binary and ternary DESs, were explored for simultaneous extraction of four phenolic acids (3-caffeoylquinic acid, 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, and 4,5-di-O-caffeoylquinic acid) from AL. The results indicated that the ternary DES composed of a 2:1:2 molar ratio of choline chloride, malic acid, and urea showed enhanced extraction yields for phenolic acids compared with conventional organic solvents and other DESs. Subsequently, the extraction parameters for the four phenolic acids by selected tailor-made DESs, including liquid-solid ratios, water content (%) in the DESs, and extraction time, were optimized using response surface methodology and the optimal extraction conditions were: extraction time, 23.5 min; liquid-solid ratio, 57.5 mL/g (mL of DES/g dry weight of plant material); water content, 54%. The research indicated that DESs were efficient and sustainable green extraction solvents for extraction of bioactive phenolic acids from natural products. Compared to the conventional organic solvents, the DESs have a great potential as possible alternatives to those organic solvents in health-related areas such as food and pharmaceuticals.

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Application of Deep Eutectic Solvents in the Synthesis of Substituted 2-Mercaptoquinazolin-4(3H)-Ones: A Comparison of Selected Green Chemistry Methods.

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