Selectivities in the oxidation of tertiary amines and pyridine derivatives by perfluoro cis-2,3-dialkyloxaziridines

Arnone, Alberto; Metrangolo, Pierangelo; Novo, Barbara; Resnati, Giuseppe

doi:10.1016/s0040-4020(98)00417-7

Cited by 17 publications

(5 citation statements)

References 56 publications

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“…Fenspiride N-oxide (FNO) (Arnone, Metrangolo, Novo, & Resnati, 1998) is an impurity of FNS resulting from the reaction of a tertiary amine with perfluoro cis-2,3 dialkyl aziridines and is produced at the carbon-carbon double bond or at the nitrogen atom under protic conditions. Fenspiride N-oxide (FNO) (Arnone, Metrangolo, Novo, & Resnati, 1998) is an impurity of FNS resulting from the reaction of a tertiary amine with perfluoro cis-2,3 dialkyl aziridines and is produced at the carbon-carbon double bond or at the nitrogen atom under protic conditions.…”

Section: Introductionmentioning

confidence: 99%

“…FNS can contain several impurities. Fenspiride N-oxide (FNO) (Arnone, Metrangolo, Novo, & Resnati, 1998) is an impurity of FNS resulting from the reaction of a tertiary amine with perfluoro cis-2,3 dialkyl aziridines and is produced at the carbon-carbon double bond or at the nitrogen atom under protic conditions. Two other impurities have been identified and isolated as metabolic products: 3-hydroxy fenspiride and 4-hydroxy fenspiride (Megel, Holmes, Zalipsky, Shemano, & Beiler, 1973).…”

Section: Introductionmentioning

confidence: 99%

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New approach for determination of the degradation products of fenspiride hydrochloride found in oral liquid formulations

Cioroiu

Caba

Prisăcaru

et al. 2018

Biomedical Chromatography

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Fenspiride hydrochloride (FNS) is used in treating chronic inflammatory diseases, most commonly as a liquid oral solution. FNS produces degradation products along with fenspiride N-oxide (FNO) and 1-phenylethyl-4-hydroxy-4-aminomethyl piperidine hydrochloride (PHAP). We aimed to develop and validate a chromatographic method in order to identify the main degradation products in the presence of other compounds from a liquid preparation. The method used a dual gradient using two buffer solutions: the first with pH 4.5 (buffer 1, pH 4.5-MeOH 90:10%, v/v) and the second with pH 2.9 (buffer 2, pH 2.9-acetronitrile-methanol, 65:15:10%, v/v/v). As mentioned, there was a modification of the organic mixture, starting with 10% methanol and ending with a mixture of acetonitrile-methanol (15:10%, v/v). The flow-rate was 1.5 mL/min. According to the elution program, experimental conditions started with 100% solution S1, which decreased to 0% and, simultaneously, solution S2 increased to 100% during the first 10 min and was maintained for a further 5 min. After 15 min, initial conditions were re-established. The linearity interval was 0.5-2 μg/mL and the minimum correlation coefficient was 0.999. The recovery factor was 100.47-103.17% and the limit of quantification was 0.19-0.332 μg/mL. Intra-day maximum precision was 4.08% for FNS and 2.65% for PHAP. This double-gradient mobile phase produced good specificity in relation to the degradation products of FNS and other constituents of the oral liquid formulation. Forced degradation studies revealed other related substances that were confirmed in mass balance analyses. Degradation products were confirmed in acidic, basic and oxidative media.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

New approach for determination of the degradation products of fenspiride hydrochloride found in oral liquid formulations

Cioroiu

Caba

Prisăcaru

et al. 2018

Biomedical Chromatography

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“…Heterocyclic N-oxides are widely used as bactericides, oxidants, catalysts, protecting groups and ligands in metal complexes [1][2][3][4]. These oxides are usually prepared by a non-catalytic oxidation process using peroxide, dioxiranes or sodium perborate as the oxidants [5][6][7]. Unfortunately, most of these reagents are toxic and/ or expensive, and large amounts of pollutants are produced during the oxidation process.…”

Section: Introductionmentioning

confidence: 99%

Heterogeneous catalytic oxidation of pyridines to N-oxides under mild conditions using tungsten-loaded TiO2

Luo

Lü

et al. 2016

Reac Kinet Mech Cat

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The heterogeneous catalytic oxidation of pyridines to pyridine N-oxides has been studied using tungsten-loaded TiO 2 as the catalyst and hydrogen peroxide as the green oxidant. The catalysts were synthesized by a simple impregnation technique and characterized by X-ray powder diffraction, Raman spectroscopy, transmission electron microscopy, energy dispersion X-ray spectroscopy, X-ray photoelectron spectroscopy. The catalytic performances of the catalysts were evaluated by the N-oxidation of pyridines with 30 wt% H 2 O 2 solution as an environmentally friendly oxidant at room temperature. These processes serve as an efficient method to prepare a variety of pyridine-N-oxides in modest to high yields, and the pyridine N-oxides could be easily separated from the heterogeneous catalytic system. This study will provide a useful strategy for preparation of heterocyclic N-oxides in the mild condition.Electronic supplementary material The online version of this article (

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“…[34][35][36] Several oxidants have been used for selective transformation, but most of the methods suffer from the use of stoichiometric amounts of corrosive acids or toxic metallic compounds and generate undesirable waste. [37][38][39][40][41] N-oxides production have been achieved by various oxidizing agents, which includes peracetic acid, m-CPBA, 32 dioxiranes, 43 caro`s acid, 44 sodium perborate in acetic acid. 45 But the use of such oxidants is not environmentally friendly due to the generation of substantial amount of effluent during the reaction process and also require a laborious work-up procedure.…”

Section: Introductionmentioning

confidence: 99%

Chloride promoted room temperature preparation of silver nanoparticles on two dimensional tungsten oxide nanoarchitectures for the catalytic oxidation of tertiary N-compounds to N-oxides

et al. 2015

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A halide ion promoted two dimensional silver tungsten-based nanomaterial was synthesized by a facile one-pot synthesis protocol at room temperature. The 2D morphology features high activity and selectivity for the oxidation of a wide range of tertiary N-compounds to their corresponding N-oxides. The morphology of Ag/WO3 materials can be varied by changing the synthesis parameters. The unique 2D plate like morphology of tungsten oxide increases adsorption sites of the support, leading to less sintering and higher dispersion of silver nanoparticles, resulting in significantly enhanced activity for the reaction. The influence of reaction parameters such as temperature, substrate to oxidant molar ratio, reaction time, etc. was investigated in detail. The catalyst was characterized by XRD, XPS, ICP-AES, TGA, FT-IR, UV-vis, Raman, SEM, TEM and STEM. Raman studies further provide mechanistic insight which proves that the formation of peroxo tungsten species is responsible for the N-oxidation reaction. High stability and recyclability of the 2D Ag/WO3 nanoplates are also observed under the investigated conditions.

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Selectivities in the oxidation of tertiary amines and pyridine derivatives by perfluoro cis-2,3-dialkyloxaziridines

Cited by 17 publications

References 56 publications

New approach for determination of the degradation products of fenspiride hydrochloride found in oral liquid formulations

New approach for determination of the degradation products of fenspiride hydrochloride found in oral liquid formulations

Heterogeneous catalytic oxidation of pyridines to N-oxides under mild conditions using tungsten-loaded TiO2

Chloride promoted room temperature preparation of silver nanoparticles on two dimensional tungsten oxide nanoarchitectures for the catalytic oxidation of tertiary N-compounds to N-oxides

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