A new synthetic route for 1,2-diketo compounds using unexpected C–C bond cleavage by PCC

Bhosale, Shrikar M.; Momin, Aadil A.; Gawade, Rupesh L.; Puranik, Vedavati G.; Kusurkar, Radhika S.

doi:10.1016/j.tetlet.2012.07.095

Cited by 8 publications

(4 citation statements)

References 56 publications

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“…Therefore, efficient synthesis of unsymmetric benzils has recently drawn significant attention. Over the past decade, several synthetic strategies for the preparation of unsymmetric benzils have been reported including the oxidation of alkynes, alkenes, or α-methylene ketones, decarboxylation of 1,3-diketones, and some others. ,, Herein, we reported a new practical synthetic route for the preparation of unsymmetric benzils from β-ketoaldehydes which can be obtained conveniently from Lewis acid catalyzed Meinwald rearrangement of chalcone epoxides, and this method has been demonstrated to be of excellent substrate scope.…”

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confidence: 99%

Practical Approach for Preparation of Unsymmetric Benzils from β-Ketoaldehydes

Ruan

Shi

et al. 2014

Org. Lett.

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An efficient and practical method for the synthesis of unsymmetric benzils from readily available β-ketoaldehydes has been developed. Various unsymmetric 1,2-diaryldiketones bearing functional groups have been obtained in good to excellent yields under mild reaction conditions. A plausible mechanism was proposed, and α,α-dichloroketone was considered as the key intermediate. The generation of α,α-dichloroketones from β-ketoaldehydes may undergo the following steps: (1) oxidation by sodium hypochlorite, (2) decarboxylation, and (3) chlorination by Cl2 generated from sodium hypochlorite.

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confidence: 99%

Practical Approach for Preparation of Unsymmetric Benzils from β-Ketoaldehydes

Ruan

Shi

et al. 2014

Org. Lett.

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“…It was observed that during the oxidation of benzoin compounds, they decomposed to aldehydes or benzil compounds rearranged to benzylic acids. It has been known that substituted benzoin/benzil compounds decompose during the oxidation [12,13,32,62,67]. Therefore, the yields of benzil reactions were found in the range of 18%-45%.…”

Section: Resultsmentioning

confidence: 99%

“…Accordingly, the % inhibition was calculated according to the formula [1-(test substance A/solvent control A)×100. MTT on cells of increasing concentrations (1,2,4,8,16,32,64, and 128 µg / mL) of each test substance over a certain range to determine the IC 50 concentrations of test substances (concentration that inhibits the proliferation of 50% of cells in the medium) were prepared. Results were analyzed using a logarithmic function with the help of the Excel program over the logarithmic curve prepared from the absorbance values obtained after the test (Table 5).…”

Section: Anticancer Activitymentioning

confidence: 99%

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Synthesis of hydroxy benzoin/benzil analogs and investigation of their antioxidant, antimicrobial, enzyme inhibition, and cytotoxic activities

2021

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In 2020, the world tried to combat the corona virus (COVID-19) pandemic. A proven treatment method specific to Severe Acute Respiratory Syndrome Coronavirus-2 (SARS-CoV-2) is still not found. In this study, seven new antiviral compounds were designed for COVID-19 treatment. The ability of these compounds to inhibit COVID-19’s RNA processing was calculated by the molecular docking study. It has been observed that the compounds can have high binding affinities especially against NSP12 (between -9.06 and -8.00 kcal/mol). The molecular dynamics simulation of NSP12-ZG 7 complex proved the stability of interaction. The synthesis of two most active molecules was performed by one-pot reaction and characterized by FT-IR, 1 H-NMR, 13 C-NMR, and mass spectroscopy. The compounds presented with their synthesis are inhibitory core structures against SARS-CoV-2 infection.

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Aminocatalytic Cross‐Coupling Approach via Iminium Ions to Different CC Bonds

Mupparapu

Battini

Battula

et al. 2014

Chemistry A European J

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Given the attractive ability of iminium ions to functionalize molecules directly at ostensibly unreactive positions, the reactivity of iminium ions, in which an α CH2 group is replaced by CO was explored. Background studies on the ability of such iminium cations to promote reactions via an iminium-catalyzed or iminium-equivalent pathway are apparently unavailable. Previously, tandem cross-coupling reactions were reported, in which an iminium ion undergoes nucleophilic 1,2-addition to give a putative three-component intermediate that abstracts a proton in situ and undergoes self-deamination followed by unprecedented DMSO/aerobic oxidation to generate α-ketoamides. However, later it was observed that iminium ions can generate valuable α-ketoamides through simple aerobic oxidation. In all reactions, iminium ions were generated in situ by reaction of 2-oxoaldehydes with secondary amines.

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A new synthetic route for 1,2-diketo compounds using unexpected C–C bond cleavage by PCC

Cited by 8 publications

References 56 publications

Practical Approach for Preparation of Unsymmetric Benzils from β-Ketoaldehydes

Practical Approach for Preparation of Unsymmetric Benzils from β-Ketoaldehydes

Synthesis of hydroxy benzoin/benzil analogs and investigation of their antioxidant, antimicrobial, enzyme inhibition, and cytotoxic activities

Aminocatalytic Cross‐Coupling Approach via Iminium Ions to Different CC Bonds

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