The asymmetric transfer hydrogenation (ATH) of ketones under aqueous conditions using tethered Ru(II)/η(6)-arene/diamine catalysts is described, as is the ATH of electron-rich substrates containing amine and methoxy groups on the aromatic rings. Although such substrates are traditionally challenging ones for ATH, the tethered catalysts work very efficiently. In the case of amino-substituted ketones, aqueous conditions give excellent results; however, for methoxy-substituted substrates, the more established formic acid/triethylamine system gives superior results.
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http://dx.doi.org/10.1021/acs.joc.5b00990 | DOI Listing |
J Org Chem
September 2024
Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno 625 00, Czech Republic.
α-Methoxyimino-β-keto esters are reported to undergo highly enantioselective catalytic transfer hydrogenation using the Noyori-Ikariya complex RuCl(-cymene)[(,)-Ts-DPEN] in a mixture of formic acid-triethylamine and dimethylformamide at 25 °C. The experimental study performed on over 25 substrates combined with computational analysis revealed that a -configured methoxyimino group positioned alpha to a ketone carbonyl leads to higher reactivity and mostly excellent enantioselectivity within this substrate class. Density functional theory calculations of competing transition states were used in rationalizing the origins of enantioselectivity and the possible role of the methoxyimino group in the reaction outcome.
View Article and Find Full Text PDFJ Org Chem
June 2024
Faculty of Sciences, Department of Chemistry, University of Chile, Las Palmeras 3425, Ñuñoa, Santiago 775000, Chile.
The mono -alkylation of arylamines using alkylamines as alkyl group donors has been scarcely investigated. In this work, we report the mono -alkylation of several arylamines (52-95%) catalyzed by the complex ruthenium-triphos in the presence of Al(OTf). Moreover, the highly reductant ability of the catalyst system allows the tandem reduction/-alkylation of nitrobenzenes in good yields (up to 80%).
View Article and Find Full Text PDFJ Chromatogr Sci
January 2025
Pharmaceutical Analytical Chemistry Department, Faculty of Pharmacy, Beni-Suef University, Al shaheed Shehata Ahmed Hegazy street, 62514 Beni-Suef, Egypt.
Cyproheptadine (CYP) is an antihistaminic and anti-serotonin drug used to improve the clinical course of hospitalized patients severely affected by COVID-19 and requiring supplemental oxygen. Thin layer chromatography (TLC)-densitometry method was developed and validated for the estimation of CYP and its impurity, dibenzosuberone and its degradation product: 10, 11-dihydroxy-dibenzosuberone. The toxicity profiles of CYP impurity and degradation product were studied and the in silico data, using pre-ADMET software, proved their toxicity.
View Article and Find Full Text PDFBiomed Chromatogr
April 2024
New Generation Materials Lab, Department of Chemistry, School of Applied Science and Humanities, Vignan's Foundation for Science Technology and Research (Deemed to be University), Guntur, Andhra Pradesh, India.
Favipiravir is an antiviral drug used for the treatment of virus-based diseases such as influenza. In this context, the development of a reliable liquid chromatography-tandem mass spectrometry method for the quantification of the drug and its impurities is necessary, particularly following the COVID-19 pandemic. Chromatographic separation was achieved on an inertial ODS column using gradient elution with a buffer containing triethylamine in high-performance liquid chromatography water and adjusting its pH with formic acid.
View Article and Find Full Text PDFJ Chromatogr Sci
November 2024
Graduate School of Pharmacy, Gujarat Technological University, Ahmedabad, Gujarat, India.
Nortriptyline HCl and pregabalin Tablet is used to treat neuropathic pain as well as mental or mood issues such as sadness, mood, feelings, anxiety and tensions. Very few analytical methods are available for the simultaneous estimation of nortriptyline HCl and pregabalin and no reports has been found for HPTLC method. In the current study, a reliable HPTLC method for the simultaneous measurement of nortriptyline HCl and pregabalin in pure forms and pharmaceutical formulations has been developed with ninhydrine post derivatization of pregabalin.
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