Synthesis of 7-hydroxy-4-methylcoumarin via the Pechmann reaction with PVP-supported phosphotungstic acid catalyst

Li, Sifang; Qi, Xin; Huang, Binbin

doi:10.1016/j.cattod.2015.12.027

Cited by 31 publications

(12 citation statements)

References 23 publications

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“…Valine is a branched chain and sugar-producing amino acid, which regulates blood sugars, provides energy for the body, and can be converted to 2-oxo-2-valerate 4-methyl ester via enzymatic processes [18]. 2-Oxo-2-valerate 4-methyl esters generate leucine via branched-chain amino acid transaminase [19]. Leucine is also a branched-chain amino acid.…”

Section: Changes In Amino Acid Metabolismmentioning

confidence: 99%

Follicular Fluid Metabolite Changes in Dairy Cows with Inactive Ovary Identified Using Untargeted Metabolomics

Bai

Zhang

et al. 2020

BioMed Research International

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The metabolism of dairy cows with inactive ovaries differs from that of healthy dairy cows. However, the molecular mechanisms underpinning these physiological and metabolic changes remain unclear. The purpose of this study was to investigate follicular fluid metabolite changes in dairy cows with inactive ovaries. Untargeted metabolomics technology and multivariate statistical analysis were used to screen differential metabolites in follicular fluid samples between inactive ovaries and estrus cows at 45-60 d postpartum. Fourteen differential metabolites were identified, consisting of amino acids, lipids, sugars, and nucleotides. When compared with healthy animal samples, eight follicular fluid metabolites were significantly increased, and six metabolites were significantly decreased in dairy cows with inactive ovaries. Metabolic pathway analyses indicated that differential metabolites were primarily involved in glycerol phospholipid metabolism, arachidonic acid metabolism, valine, leucine and isoleucine biosynthesis, and phenylalanine metabolism. These metabolites and their enrichment pathways indicate that the enhancement of lipid metabolism and the weakening of carbohydrate production of amino acids in dairy cows with impaired follicular development. Overall, these data provide a better understanding of the changes that could affect follicular development during the postpartum period and lay the ground for further investigations.

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Section: Changes In Amino Acid Metabolismmentioning

confidence: 99%

Follicular Fluid Metabolite Changes in Dairy Cows with Inactive Ovary Identified Using Untargeted Metabolomics

Bai

Zhang

et al. 2020

BioMed Research International

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“…Various catalysts such as mineral acids like H 2 SO 4 , HCl, H 3 PO 4 , CF 3 COOH, HClO 4, ClSO 3 H, PTSA, and oxalic acid as well as Lewis acids such as ZnCl 2 , FeCl 3 , SnCl 4 , SnCl 2 ·H 2 O, TiCl 4 , AlCl 3 , ZrCl 4, InCl 3 , BiCl 3 , Sm(NO 3 ) 3 , BF 3 ·H 2 O, CAN, Cu(ClO 4 ) 2 , BaCl 2 , and NbCl 5 were also reported in the conventional synthesis of coumarin via Pechmann condensation. 13 Similarly, different heterogeneous catalysts were also employed for Pechmann condensation such as Al-MCM-41, 14 Al-SBA-1 molecular sieves, 15 Keggin structures heteropolyacids, 16 graphite-montmorillonite K10, 17 H 14 [NaP 5 W 30 O 110 ], 18 silica triflate, 19 mesoporous zirconium phosphate, 20 ZrOCl 2 ·8H 2 O/SiO 2 , 21 pentafluorophenylammonium triflate, 22 periodic mesoporous silica chloride, 23 melamine–formaldehyde resin-supported H + , 24 PEG-SO 3 H, 25 poly(4-vinylpyridinium) hydrogen sulfate, 26 PVP-supported phosphotungstic acid, 27 poly(4-vinylpyridine)-supported copper iodide, 28 1-butyl-3-methylimidazolium chloroaluminate, and 1-butyl-3-methylimidazolium hexafluorophosphate ionic liquid. 29…”

Section: Introductionmentioning

confidence: 99%

Heterogeneously Catalyzed Pechmann Condensation Employing the Tailored Zn_0.925Ti_0.075O NPs: Synthesis of Coumarin

Jadhav

Sakate²,

Rasal³

et al. 2019

ACS Omega

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A novel heterogeneous catalytic method was developed for the synthesis of coumarin and its derivatives using the Ti(IV)-doped ZnO matrix forming catalyst Zn 0.925 Ti 0.075 O having a high surface area and good Lewis acidity. The catalyst shows high activity toward a broad spectrum of the substituted phenols with β-ketoesters such as ethyl acetoacetate, ethyl butyryl acetate, ethyl benzoyl acetate, and so forth in good yields over short reaction times during the synthesis of coumarins. The methodology was further extended for the synthesis of ayapin molecules. The catalyst also shows recycle activity up to seven cycles with very good stability.

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“…Compared with the Amberlyst-15, the H-β and TS-OS-SO 3 H materials contained fewer acid sites per gram of catalyst ( Table 1 ). In general, the catalytic activity on the synthesis of 7-hydroxy-4-methylcoumarin could be related to the amount of acid sites [ 36 ]. However, the sulfonic acid functionalized hybrid silica with an acidity of 1.24 mmol H g −1 , four times lower than Amberlyst-15, exhibited a yield higher than expected.…”

Section: Resultsmentioning

confidence: 99%

Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts

et al. 2017

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A suitable methodology of synthesis of coumarin derivatives by Pechmann reaction over heterogeneous solid acid catalysts in a free solvent media under microwave irradiation is described. Resorcinol, phenol and ethyl acetoacetate were selected as model reactants in the Pechmann condensation. The catalytic activity of several materials—Amberlyst-15, zeolite β and sulfonic acid functionalized hybrid silica—in solvent-free microwave-assisted synthesis of the corresponding coumarin derivatives has been investigated in detail. 7-Hydroxy-4-methylcoumarin and 4-methylcoumarin were obtained in 97% and 43% yields, respectively, over Amberlyst-15. This was the most active catalyst in the Pechmann reaction under studied conditions.

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Synthesis of 7-hydroxy-4-methylcoumarin via the Pechmann reaction with PVP-supported phosphotungstic acid catalyst

Cited by 31 publications

References 23 publications

Follicular Fluid Metabolite Changes in Dairy Cows with Inactive Ovary Identified Using Untargeted Metabolomics

Follicular Fluid Metabolite Changes in Dairy Cows with Inactive Ovary Identified Using Untargeted Metabolomics

Heterogeneously Catalyzed Pechmann Condensation Employing the Tailored Zn_0.925Ti_0.075O NPs: Synthesis of Coumarin

Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts

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Synthesis of 7-hydroxy-4-methylcoumarin via the Pechmann reaction with PVP-supported phosphotungstic acid catalyst

Cited by 31 publications

References 23 publications

Follicular Fluid Metabolite Changes in Dairy Cows with Inactive Ovary Identified Using Untargeted Metabolomics

Follicular Fluid Metabolite Changes in Dairy Cows with Inactive Ovary Identified Using Untargeted Metabolomics

Heterogeneously Catalyzed Pechmann Condensation Employing the Tailored Zn0.925Ti0.075O NPs: Synthesis of Coumarin

Coumarin Derivatives Solvent-Free Synthesis under Microwave Irradiation over Heterogeneous Solid Catalysts

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Heterogeneously Catalyzed Pechmann Condensation Employing the Tailored Zn_0.925Ti_0.075O NPs: Synthesis of Coumarin