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An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins.

ABSTRACT: Herein, we report a green and efficient synthetic route for the construction of diverse functionalized coumarins in good-to-excellent yields (60-98%) via the Pechmann condensation. The optimized synthetic route involves a biodegradable, reusable, and inexpensive deep eutectic solvent (DES) of choline chloride and l-(+)-tartaric acid in a ratio of 1:2 at 110 °C. Interestingly, phloroglucinol and ethyl acetoacetate, upon reaction, furnished the functionalized coumarin (20) in 98% yield within 10 min. On the other front, the same DES at relatively lower reaction temperature (90 °C) was found to provide the bis-coumarins in decent yields (81-97%) within 20-45 min. Moreover, this particular method was found to be quite effective for large-scale coumarin synthesis without noteworthy reduction in the yields of the desired products. Noticeably, in this versatile approach, the DES plays a dual role as solvent as well as catalyst, and it was effectively recycled and reused four times with no significant drop-down in the yield of the product.

SUBMITTER: Rather IA

PROVIDER: S-EPMC8973037 | biostudies-literature | 2022 Mar

REPOSITORIES: biostudies-literature

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An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins.

Rather Ishfaq Ahmad IA Ali Rashid R

ACS omega 20220315 12

Herein, we report a green and efficient synthetic route for the construction of diverse functionalized coumarins in good-to-excellent yields (60-98%) via the Pechmann condensation. The optimized synthetic route involves a biodegradable, reusable, and inexpensive deep eutectic solvent (DES) of choline chloride and l-(+)-tartaric acid in a ratio of 1:2 at 110 °C. Interestingly, phloroglucinol and ethyl acetoacetate, upon reaction, furnished the functionalized coumarin (<b>20</b>) in 98% yield with ...[more]

PMID: 35382332

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Project description:In recent years, deep eutectic solvent (DES) has attracted comprehensive attention on the extraction of natural products, and is regarded as an alternative to traditional organic solvents for the environmental advantages. Twenty-six DESs were compared for their extraction yield of total flavonoids and isovitexin (the main flavonoid in Celtis sinensis) from Celtis sinensis. The results show that the extraction yields of total flavonoids by betaine/glycolic acid (DES8), ethylamine hydrochloride/1,2-propanediol (DES12) and tetrapropylammonium bromide/lactic acid (DES17) are the highest, while the extraction yields of isovitexin by ethylene glycol/malonic acid (DES23), ethylene glycol/glycolic acid (DES24) and 1,2-propanediol/glycolic acid (DES26) are the highest. The extraction conditions using the above six DESs were further optimized systematically. Under optimum conditions, the extraction rates of total flavonoids and isovitexin can be increased up to 95.39 and 10.58 mg g-1, respectively, which were significantly higher than that of methanol extraction. In order to exclude the effect of DESs on the bioactivity of Celtis sinensis extract, the macroporous resin D-101 was used to purify the total flavonoids from DESs extract, and the recovery rates of flavonoids from the above six kinds of DESs were all over 80%. Next, the anti-inflammatory activity of DES extracts was compared using a lymphocyte transformation experiment. The result showed that the inhibition rate of the DES24 extract on the proliferation of Con A-activated T cells was up to 72% with an IC50 value of 124.8 μg mL-1. None of the DESs extracted exhibited cytotoxicity on normal T cells. The mechanism of the anti-inflammatory activity against Con A-activated T cells may be that DES24 flavonoids extract induced the apoptosis of inflammatory T cells, and activated the expression of pro-apoptotic protein. Taken together, DES has showed significant advantages on the extraction of natural products for the relatively mild extraction condition, high yield and environmental-friendliness.

Dataset Information

An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins.

Publications

An Efficient and Versatile Deep Eutectic Solvent-Mediated Green Method for the Synthesis of Functionalized Coumarins.

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