1532-72-5Relevant articles and documents
Copper(II)-catalyzed electrophilic amination of quinoline N-oxides with O-benzoyl hydroxylamines
Li, Gang,Jia, Chunqi,Sun, Kai,Lv, Yunhe,Zhao, Feng,Zhou, Kexiao,Wu, Hankui
, p. 3207 - 3210 (2015)
Copper acetate-catalyzed C-H bond functionalization amination of quinoline N-oxides was achieved using O-benzoyl hydroxylamine as an electrophilic amination reagent, thereby affording the desired products in moderate to excellent yields. Electrophilic amination can also be performed in good yield on a gram scale. This journal is
Elimination of Carbon Monoxide by Electron Impact on Quinoline N-oxide, Carbostyril and 8-Hydroxyquinoline
Blumenthal, Thomas,Gillis, Richard G.,Porter, Quentin N.,Yeoh, Li Li
, p. 247 - 249 (1991)
Under electron impact, the molecular ions of quinoline N-oxide, carbostyril and 8-hydroxyquinoline lose carbon monoxide giving a fragment ion C8H7N (m/z 117), which was shown by collision-activated dissociation in each case to have the structure of the molecular ion of indole.Its formation from 8-hydroxyquinoline requires an unusual rearrangement.Isoquinoline N-oxide loses HCN rather than CO and gives a fragment which has the structure of the molecular ion of benzofuran.When the first three compounds were subjected to flash vacuum pyrolysis, quinoline N-oxide at 500-700 deg C gave carbostyril and indole was detected by gas chromatography/mass spectrometry.At 900 deg C carbostyril and 8-hydroxyquinoline both gave indole in small amounts, detected by gas chromatography/mass spectrometry.
Method for preparing sulfone and N-oxygen compound by using green and efficient oxidation system
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Paragraph 0030-0032, (2021/01/29)
The invention discloses a method for preparing sulfone and N-oxygen compound by using a green and efficient oxidation system. The method comprises the following steps of: by using a tertiary amine compound or aromatic thioether or fatty thioether compound as a raw material, H2O2 as an oxidant, methanol as a reaction solvent and potassium carbonate as an alkali, introducing sulfuryl fluoride 5O2F2gas as an accelerator; performing stirring at room temperature under a sealed condition for oxidation reaction; and after finishing the reaction, filtering to remove solid potassium carbonate, dryingto remove water, filtering to obtain a crude product, and finally carrying out column chromatography separation to obtain a pure product. Tertiary amine is oxidized into an N-oxygen compound, and thethioether is oxidized into sulfone. According to the method, the sulfuryl fluoride (SO2F2) which is very cheap and easy to obtain is used as the reaction promoter, green and environment-friendly hydrogen peroxide (H2O2) is used as an oxidizing agent, and so that the yield of the reaction is generally high; after the reaction, byproducts are only water and inorganic salts (SO4 and F) whichare easy to remove and free of pollution, and the green and efficient oxidation system can be realized, and therefore, the method is suitable for large-scale industrial production.
Waste-minimized synthesis of C2 functionalized quinolines exploiting iron-catalysed C-H activation
Ferlin, Francesco,Zangarelli, Agnese,Lilli, Simone,Santoro, Stefano,Vaccaro, Luigi
supporting information, p. 490 - 495 (2021/01/28)
Herein we present an efficient and regioselective iron-catalyzed methodology for the external oxidant-free functionalization of quinoline-N-oxides. The protocol, based on the use of inexpensive and easily accessible FeSO4, showed broad applicability to a wide range of substrates. An additional green feature of this synthetic methodology is H2O being the only by-product. Experimental and computational investigations provide support to a mechanism based on a facile C-H activation event. The green efficiency of the process has also been carefully assessed using: (i) metrics related to the synthetic process (AE, Yield, 1/SF, MRP and RME); (ii) safety/hazard metrics (SHZI and SHI); and (iii) metrics related to the metal used as the catalyst (Abundance, OEL and ADP). In addition to the many advantages of this protocol related to the green iron catalyst used and the safety/hazard features of the process, an E-factor value of ca. 0.92 (84 to >99% reduction compared to known protocols) evidently confirms the sustainable efficiency of the procedure presented. Practical utility has also been demonstrated by performing the reaction efficiently on a multi-gram scale. This journal is
