Aqueous high-temperature chemistry of carbo- and heterocycles. 18. Six-membered heterocycles with one nitrogen atom: pyridine, quinoline, acridine, and phenanthridine systems

Katritzky, Alan R.; Łapucha, Andrzej R.; Siskin, Michael

doi:10.1021/ef00034a013

Cited by 16 publications

(33 citation statements)

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“…Acridin-9(10H)-one is produced not only by monooxygenases but also abiotically from acridine in water at 350ЊC [32]; it is an im-purity in some commercial lots of acridine [33]. Reduction of acridine to 9,10-dihydroacridine may occur catalytically or abiotically in water at 350ЊC [32]; this product has antioxidant properties [34]. Reduction of acridine to 9,10-dihydroacridine may occur catalytically or abiotically in water at 350ЊC [32]; this product has antioxidant properties [34].…”

Section: Discussionmentioning

confidence: 99%

“…A different pathway probably produces 4-hydroxyacridine; heterocyclic compounds may be oxidized to arene oxides by cytochrome P450 monooxygenases [31] and arene oxides may be hydrolyzed by epoxide hydrolases to produce trans-dihydrodiols or be converted nonenzymatically to phenols [25]. Acridin-9(10H)-one is produced not only by monooxygenases but also abiotically from acridine in water at 350ЊC [32]; it is an im-purity in some commercial lots of acridine [33]. However, the amounts we detected in the starting material and in abiotic controls were negligible compared to those produced in cultures of M. vanbaalenii.…”

Section: Discussionmentioning

confidence: 99%

“…However, the amounts we detected in the starting material and in abiotic controls were negligible compared to those produced in cultures of M. vanbaalenii. Reduction of acridine to 9,10-dihydroacridine may occur catalytically or abiotically in water at 350ЊC [32]; this product has antioxidant properties [34].…”

Section: Discussionmentioning

confidence: 99%

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Biotransformation of acridine by Mycobacterium vanbaalenii

Sutherland

Heinze

Pearce

et al. 2009

Enviro Toxic and Chemistry

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Cultures of Mycobacterium vanbaalenii strain PYR-1 in a liquid medium were exposed to the toxic environmental contaminant acridine (260 microM). After incubation for 7 d, the cultures were extracted with ethyl acetate. Metabolites were purified using high-performance liquid chromatography and analyzed by mass spectrometry and 1H nuclear magnetic resonance spectroscopy. Four metabolites, 9,10-dihydroacridine, 4-hydroxyacridine, acridine cis-1 ,2-dihydrodiol, and acridin-9(10H)-one, were identified.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Biotransformation of acridine by Mycobacterium vanbaalenii

Sutherland

Heinze

Pearce

et al. 2009

Enviro Toxic and Chemistry

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“…In addition to these studies, reactions of cholesterol, n -C 10 aliphatic compounds, and nitrogen-containing heterocycles were investigated using clay catalysts over long reaction times (1–13.5 days).…”

Section: Reactions Catalyzed By Solid Acid/base Catalysts In Subandscwmentioning

confidence: 99%

Solid Acid/Base Catalysis in Sub- and Supercritical Water

Akizuki

Oshima

2018

Ind. Eng. Chem. Res.

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Solid acid/base catalysis in sub-and supercritical water (Sub&SCW) is a promising method to control organic reactions such as biomass conversions to chemicals and fuels, organic synthetic reactions, and degradation reactions. Synergistically using the unique characteristics of Sub&SCW and the catalytic properties of solid acid/base compounds, high reaction rates and/or high product selectivity can be achieved. This Review provides an overview of the use of solid acid/base catalysts for Sub&SCW reactions. Recent progress in the elucidation of the acid/base catalytic properties of solid catalysts in Sub&SCW and the effect of water properties on the catalysis is introduced. In addition, the application of solid acid/base catalysts in several research fields and the stability of these catalysts during reactions is discussed.

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“…SCW has also been reported to promote the removal of heteroatoms of heavy oil including N, S, Ni, and V. ,, In this work, we focus on the denitrogenation process of heavy oil in SCW and choose isoquinoline as the research subject. , Houser et al − demonstrated that almost 80% of isoquinoline is converted after reaction for 120 h at 450 °C and 32.27 MPa, and the main products are toluene, ethylbenzene, and o-xylene. Houser − also proposed an isoquinoline–SCW reaction scheme, as shown in Figure , that indicated two ring-opening pathways.…”

Section: Introductionmentioning

confidence: 99%

Quantum Chemistry Calculations on the Mechanism of Isoquinoline Ring-Opening and Denitrogenation in Supercritical Water

Wang

et al. 2017

Ind. Eng. Chem. Res.

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Computational studies at the M06/6-311G(d,p) and M06-2X/6-311+G(d,p) levels were performed to explore the detailed mechanism of isoquinoline ring-opening and denitrogenation in a supercritical water system. Three reaction paths with the same product, 2-(2-oxoethyl) benzaldehyde, were supported by the computational results. The rate-limiting step in the major degradation reaction is an addition reaction at the N position. H2O is added to both the 1C–2N double bond (1C–2N addition reaction) and the 2N–3C double bond (2N–3C addition reaction) of the isoquinoline molecule, where the oxygen of H2O is added to the carbon atom. The energy barrier of the 1C–2N addition reaction is 52.7 kcal/mol, while that of 2N–3C addition (from Path 6) is 60.1 kcal/mol. From catalysis by two water molecules, the barrier of 1C–2N addition (Reaction (1)) is reduced to 27.5 kcal/mol. Catalysis from water molecule clusters is shown to considerably affect the process of isoquinoline ring-opening and denitrogenation, as indicated by comparing the reaction energy barrier heights with and without water catalysts.

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Aqueous high-temperature chemistry of carbo- and heterocycles. 18. Six-membered heterocycles with one nitrogen atom: pyridine, quinoline, acridine, and phenanthridine systems

Cited by 16 publications

References 0 publications

Biotransformation of acridine by Mycobacterium vanbaalenii

Biotransformation of acridine by Mycobacterium vanbaalenii

Solid Acid/Base Catalysis in Sub- and Supercritical Water

Quantum Chemistry Calculations on the Mechanism of Isoquinoline Ring-Opening and Denitrogenation in Supercritical Water

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