Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives

Payne, Daniel T.; Zhao, Yiming; Fossey, John S.

doi:10.1038/s41598-017-01950-7

Cited by 6 publications

(7 citation statements)

References 27 publications

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“…The final step produced high yields (96–98%) of alkyl derivatives of Meldrum’s acid ( 5a,b ) from compound 3 when it was treated with alkyl bromide ( 4a,b ) in a DMF solvent with potassium carbonate as a base for 18 h at room temperature (Table ). ,, …”

Section: Resultsmentioning

confidence: 99%

Meldrum-Based-1H-1,2,3-Triazoles as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, Molecular Docking Studies, and In Silico Approach

et al. 2023

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A series of novel alkyl derivatives (2−5a,b) and 1H-1,2,3-triazole analogues (7a−k) of Meldrum's acid were synthesized in a highly effective way by using "click" chemistry and screened for in vitro α-glucosidase inhibitory activity to examine their antidiabetic potential. 1 H NMR, 13 C-NMR, and highresolution electrospray ionization mass spectra (HR-ESI-MS) were used to analyze each of the newly synthesized compounds. Interestingly, these compounds demonstrated high to moderate αglucosidase inhibitory potency having an IC 50 range of 4.63−80.21 μM. Among these derivatives, compound 7i showed extraordinary inhibitory activity and was discovered to be several times more potent than the parent compound Meldrum (1) and the standard drug acarbose. Later, molecular docking was performed to understand the binding mode and the binding strength of all the compounds with the target enzyme, which revealed that all compounds are well fitted in the active site of α-glucosidase. To further ascertain the structure of compounds, suitable X-ray single crystals of compounds 5a, 7a, and 7h were developed and studied. The current investigation has shown that combining 1H-1,2,3-triazole with the Meldrum moiety is beneficial. Furthermore, this is the first time that the aforementioned activity of these compounds has been reported.

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Section: Resultsmentioning

confidence: 99%

Meldrum-Based-1H-1,2,3-Triazoles as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, Molecular Docking Studies, and In Silico Approach

et al. 2023

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“…Two carbon elongation of aldehyde to carboxylic acid by Knoevenagel condensation with 14 , reduction of olefin, and decarboxylation has already been reported in the literature, but analogous reactions starting from ketone have not been reported yet . The key synthetic challenge in the above route was the diastereoselective reduction of 12 .…”

Section: Introductionmentioning

confidence: 93%

Diastereoselective Synthesis of a cis-1,3-Disubstituted Cyclobutane Carboxylic Acid Scaffold for TAK-828F, a Potent Retinoic Acid Receptor-Related Orphan Receptor (ROR)-γt Inverse Agonist

Majima

Yamano

2021

J. Org. Chem.

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A scalable synthesis of the cis-1,3-disubstituted cyclobutane carboxylic acid scaffold of TAK-828F (1) has been developed, featuring the diastereoselective reduction of a cyclobutylidene Meldrum's acid derivative with NaBH 4 . Controlling acidic impurities was crucial for improving the diastereomeric ratio by recrystallization. Furthermore, reaction optimization and the streamlining of several steps established a scalable synthetic method free from column chromatography purification with an overall yield improved from 23 to 39%.

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“…[26] Another method for the synthesis of HCAL and its derivatives (11-67% yield) is through a five-step process from the Knoevenagel condensation of aldehydes with Meldrum's acid. [30] Moreover, Frost et al reported the hydrosilylation of Meldrum's acid by a multi-step process, using palladium or molybdenum catalysts. [31,32] Instead of these complex multi-step processes, selective hydrogenation of CAL to a HCAL reaction does not produce any corrosive byproduct or toxic waste.…”

Section: Introductionmentioning

confidence: 99%

Biologically bound nickel as a sustainable catalyst for the selective hydrogenation of cinnamaldehyde

Johar

McElroy

Rylott

et al. 2022

Applied Catalysis B: Environmental

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Ethylenation of aldehydes to 3-propanal, propanol and propanoic acid derivatives

Cited by 6 publications

References 27 publications

Meldrum-Based-1H-1,2,3-Triazoles as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, Molecular Docking Studies, and In Silico Approach

Meldrum-Based-1H-1,2,3-Triazoles as Antidiabetic Agents: Synthesis, In Vitro α-Glucosidase Inhibition Activity, Molecular Docking Studies, and In Silico Approach

Diastereoselective Synthesis of a cis-1,3-Disubstituted Cyclobutane Carboxylic Acid Scaffold for TAK-828F, a Potent Retinoic Acid Receptor-Related Orphan Receptor (ROR)-γt Inverse Agonist

Biologically bound nickel as a sustainable catalyst for the selective hydrogenation of cinnamaldehyde

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