Beitrag zur Oxydation von Pyridin‐aldehyden

Klosa, Josef

doi:10.1002/ardp.19552880816

Cited by 5 publications

(4 citation statements)

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“…Chemistry Condensation of 3-acetyl-4-hydroxycoumarin 1 [31] with 4fluoroaniline in absolute ethyl alcohol using a catalytic amount of glacial acetic acid afforded the corresponding Schiff's base 2 (Scheme 1). The chalcone derivative 3 [32] was synthesized through a Claisen-Schmidt condensation reaction of the precursor 3-acetyl-4-hydroxycoumarin 1 and 4-fluorobenzaldehyde according to the reported procedures (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

Batran

Dawood

Elseginy

et al. 2017

Archiv der Pharmazie

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Breast and cervical cancers are the most common gender-specific cancers affecting women worldwide. In this investigation, we highlighted the synthesis, VEGFR-2 and p38α MAPK inhibitory activity of new series of fluorinated coumarin-based derivatives featuring a variety of bioactive chemical moieties attached or fused to the coumarin nucleus at the 3 and/or 4 position. The bioactive inhibitors were further assessed for their anti-proliferative effect against human MCF-7 breast cancer and HeLa cervical cancer cell lines, respectively. Most of the tested compounds showed potent preferential inhibition effects against human VEGFR-2 and remarkable anticancer activities in the human breast cancer cell line MCF-7. Compounds 29, 24, and 2 displayed the highest inhibitory activity against VEGFR-2 (94% inhibition) and they were the most potent anticancer agents toward MCF-7 cancer cells with IC values of 7.90, 8.28, and 8.30 μg/mL, respectively. Compound 13 inhibited p38α MAPK phosphorylation with a significant reduction in % cell viability against HeLa cancer cells at 10 and 30 µM. Docking experiments carried out on VEGFR-2 and p38 MAPK crystallographic structures revealed that the active compounds bind to the active sites through H-bonds, arene-cation, and hydrophobic π-π interactions. QSAR analysis demonstrated considerable correlation coefficient (R = 0.76969) and root mean square error (RMSE = 0.10446) values. Also, the residual values between the experimental pIC and predicted pIC are very close, indicating the reliability of the established QSAR model.

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Section: Resultsmentioning

confidence: 99%

New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

Batran

Dawood

Elseginy

et al. 2017

Archiv der Pharmazie

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“…Besides the values for niacin, the values for the sum of niacin and 3-pyridinealdehyde are also shown, since pyridinealdehyde can easily be oxidised in the liquid phase to the acid. 17 The maximum conversions to the sum of niacin and aldehyde presented in the table reflect the possibilities to make use of the most ideal process design, in which all or practically all incoming 3-picoline is converted, so that no separation or recirculation of unconverted 3-picoline is required.…”

Section: Oxidation Of 3-picoline To Niacin and 3-pyridinealdehydementioning

confidence: 99%

“…2-Pyridinealdehyde is easily oxidised by air in the liquid phase. 17 With this in mind, and considering that a substantial decarboxylation of picolinic acid is obtained in the vapour phase oxidation of 2-picoline, another way to prepare picolinic acid is suggested: first to oxidise 2-picoline to the 2-pyridinealdehyde in the vapour phase by air, and then in a second step to oxidise the aldehyde to picolinic acid in the liquid phase. Attempts with vapour phase oxidation of 2-picoline to 2-pyridinealdehyde have been reported for a number of catalysts.Y.…”

Section: Introductionmentioning

confidence: 99%

Preparation of pyridinemonocarboxylic acids by catalytic vapour phase oxidation of alkylpyridines. I. Oxidation of 2‐ and 3‐picoline and decarboxylation of 2‐ and 3‐pyridinecarboxylic acid in the vapour phase

Järås¹,

Lundin²

1977

J. Appl. Chem.

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The vapour phase oxidation of 2‐picoline with air using a singly promoted vanadium catalyst (V2O5/SnO2, mole ratio 1/1.5), at a temperature of 375°C and a space velocity of 6130 h−1, gave a 69% conversion with a selectivity of 64% for 2‐pyridinealdehyde. No pyridoin formation was detected. In the vapour phase oxidation of 3‐picoline using a doubly promoted vanadium catalyst (V2O5‐TiO2‐Na2O with V/Ti/Na=100/20/1.15) at a temperature of 400°C and a space velocity of 1450 h−1, a 94% conversion of 3‐picoline was obtained with a selectivity of 51% for niacin (3‐pyridinecarboxylic acid) and 1% for 3‐pyridinealdehyde. By varying the atom ratio V/Ti, the catalyst V/Ti = 100/25 was found to be the most active one. The decarboxylation of 2‐ and 3‐pyridinecarboxylic acid in the vapour phase was also investigated under the conditions used in the oxidation of the picolines to the acids. At 350°C about 90% decarboxylation of picolinic acid occurs under these conditions, while only a few per cent of the niacin decarboxylated to pyridine between 300 and 500°C.

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“…2-Acetyl-3hydroxy-1H-phenalen-1-one (1) was obtained in a 2-step reaction from phenalene-1,3-dione by cyclocondensation with diethyl malonate, followed by a ring-opening reaction in sodium hydroxide solution and subsequent spontaneous decarboxylation upon acidification as described recently [5]. Attempts to obtain 2-acetyl-3-hydroxy-1H-phenalen-1-one (1) in a one step reaction by direct acetylation of phenalene-1,3-dione using acetic acid with acid catalysts as described in several heterocyclic systems [7] was not successful.…”

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confidence: 99%

Synthesis of 10‐Aryl‐10H‐naphtho[1,8a,8‐fg]indazol‐7‐ones

Stadlbauer

Hojas

2003

Journal of Heterocyclic Chem

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Dedicated to Professor Thomas Kappe on the occasion of his 70th birthday3 -H y d r o x y -2 -[ 1 -( a r y l h y d r a z o n o ) e t h y l ] -1H-phenalen-1-ones 3, obtained from 2-acetyl-3-hydroxy-1H-phenalen-1-one (1) and arylhydrazines 2, cyclize under acidic conditions to 8-methyl-10-aryl-10H-naphtho-[1,8a,8-fg]indazol-7-ones 4. Indazoles 4 are also obtained from 2-acetyl-3-hydroxy-1H-phenalen-1-one (1) and arylhydrazines 2 in a one-pot reaction. 2-Acetyl-3-azido-1H-phenalen-1-one (6) does not give 8-methyl-9-arylamino-9H-naphtho [1,8a,8-fg]indazol-7-ones via azide decomposition but gives again by nucleophilic replacement of the azide moiety in 6 the indazole 4. J. Heterocyclic Chem., 40, 753(2003).Indazole derivatives are of great interest because of their pharmaceutical activity, use in agrochemistry, in dye chemistry and in photographic processes [2]. Whereas the basic ring system of indazole is investigated thoroughly, polyfused derivatives are rarely described. In the course of our investigations of ring closure reactions of phenalene derivatives [3-5] we focused our interest on the synthesis of indazoles of type A (typus of a 1H-indazole) and of type B (typus of a 2H-indazole). In the literature, only one example of such an indazole of type A is described as a follow-up product in the ring enlargement of acenaphthenequinone [6]. Scheme 1We started our synthesis program with a 2-acyl-1-hydrazinoarene synthon, which should give in the cyclization step the formation of one new N-C bond. As the first step in this reaction the hydrazinolysis of 2-acetyl-3-hydroxy-1H-phenalen-1-one (1) was planned. 2-Acetyl-3-hydroxy-1H-phenalen-1-one (1) was obtained in a 2-step reaction from phenalene-1,3-dione by cyclocondensation with diethyl malonate, followed by a ring-opening reaction in sodium hydroxide solution and subsequent spontaneous decarboxylation upon acidification as described recently [5]. Attempts to obtain 2-acetyl-3-hydroxy-1H-phenalen-1-one (1) in a one step reaction by direct acetylation of phenalene-1,3-dione using acetic acid with acid catalysts as described in several heterocyclic systems [7] was not successful.The reaction of 2-acetyl-3-hydroxy-1H-phenalen-1-one (1) with arylhydrazines 2 was performed either in dimethylformamide without catalyst in the case of phenylhydrazine (2a) or with glacial acetic acid and sulfuric acid as catalyst in the case of 4-nitrophenylhydrazine (2b). In both cases 3-hydroxy-2-[1-(arylhydrazono)ethyl]-1H-phenalen-1-ones 3 were obtained in 48 and 97% yield, respectively.Because of the high reactivity of 3a, in all experiments, traces of the follow-up ring closed compound 4 a w e r e

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Beitrag zur Oxydation von Pyridin‐aldehyden

Cited by 5 publications

References 1 publication

New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

New Coumarin Derivatives as Anti‐Breast and Anti‐Cervical Cancer Agents Targeting VEGFR‐2 and p38α MAPK

Preparation of pyridinemonocarboxylic acids by catalytic vapour phase oxidation of alkylpyridines. I. Oxidation of 2‐ and 3‐picoline and decarboxylation of 2‐ and 3‐pyridinecarboxylic acid in the vapour phase

Synthesis of 10‐Aryl‐10H‐naphtho[1,8a,8‐fg]indazol‐7‐ones

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