1824-81-3Relevant articles and documents
Nucleophilic Reaction of Electron-deficient Pyridone Derivatives. II. Ring Transformation of 1-Substituted 3,5-Dinitro-4-pyridones with Sodio β-Keto Esters
Matsumura, Eizo,Ariga, Masahiro,Tohda, Yasuo
, p. 2891 - 2894 (1980)
The reaction of 1-substituted 3,5-dinitro-4-pyridones with diethyl sodio-3-oxopentanedioate give 1-substituted 3,5-bis(ethoxycarbonyl)-4-pyridones and sodio-1,3-dinitro-2-propane.On the other hand, the reactions of the 4-pyridones (1b, 1c, and 1d) with ethyl sodioacetoacetate give ethyl 4-hydroxy-3,5-dinitrobenzoate together with aminopyridine homologues, and that of 1a gives furopyridine derivative.On the basis of the concept of soft and hard acids and bases, a stepwisenucleophilic attack of the anion of β-keto esters at the electrophilic center of the 2 and 6-positions or 2 and 3-positions of the 4-pyridones is interpret the variations of the reaction courses.
Syntheses, spectroscopy, electrochemistry, EPR, PXRD-structure and DFT/TD-DFT of bis[2-oxo-1-naphthaldehydato-κO,O’]copper(II)
Enamullah, Mohammed,Joy, Baitul Alif,Islam, Mohammad Khairul
, p. 56 - 64 (2019)
Reaction of N-2-(R-pyridyl)-2-hydroxy-1-naphthaldimine {R = H (HL1), 4-CH3 (HL2) and 6-CH3 (HL3)} with copper(II) nitrate provides the new complex of bis[2-oxo-1-naphthaldehydato-κO,O’]copper(II) (1) via in-situ hydrolysis of the Schiff base back to 2-hydroxy-1-naphthaldehyde (HL′). Elemental analyses reveal that there are no nitrogen atoms in the complex. X-ray diffraction (PXRD) data indicate that the complex is monoclinic with space group P21/a and Z = 2 and that the ligand acts as bidentate through O?O-chelate system forming a bis-complex with O2O2-coordination sphere around the copper(II) ion. Electrochemical results show two quasi-reversible one electron charge transfer processes attributed to [Cu(L′)2]2?/[Cu(L′)2]? and [Cu(L′)2]?/[Cu(L′)2] (L’ = deprotonated aldehyde) couples in acetonitrile. The magnetic data confirm the paramagnetic property of the complex with one unpaired electron in the metallic centre. The results suggest that the complex assumes a geometry between tetrahedral and square-planar supported by DFT calculations. Thermal analysis shows an irreversible phase transformation from solid to isotropic liquid phase. EPR spectrum in chloroform exhibits an isotropic pattern with four lines due to nuclear hyperfine splitting from the copper(II) ion with spin 3/2. The structural analyses, electrochemical and paramagnetic properties of these complexes explore greater interests for their use in the supramolecular chemistry.
Electrocyclic Ring-Opening of 1,2,4-Oxadiazole[4,5-a]piridinium Chloride: a New Route to 1,2,4-Oxadiazole Dienamino Compounds
Carella, Stefano,Memeo, Misal Giuseppe,Quadrelli, Paolo
, p. 1209 - 1221 (2019)
1,2,4-Oxadiazole[4,5-a]piridinium chloride adds nucleophiles to undergo electrocyclic ring opening affording 1,2,4-oxadiazole dienamino derivatives. These pyridinium salts represent a special class of Zincke salts that are prone to rearrange when treated
Electronic, infrared, mass spectrometry and thermal studies on the reaction of 2-amino-6-methylpyridine with π-acceptors
Madrahimov, Sherzod,Mostafa, Adel,Yempally, Veeranna,Fadlallah, Joelle,AlQaradawi, Siham Y.
, (2020)
The spectrophotometric characteristics of the solid charge-transfer molecular complexes (CT) formed in the reaction of the electron donor 2-amino-6-methylpyridine (2A6MPy) with the π-acceptors tetracyanoethylene (TCNE), 2,3-dichloro-5,6-dicyano-1,4-benzoq
Ligand compound for copper catalyzed aryl halide coupling reaction, catalytic system and coupling reaction
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Paragraph 0111-0118; 0120, (2021/05/29)
The invention provides a ligand compound capable of being used for copper catalyzed aryl halide coupling reaction, the ligand compound is a three-class compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group, and the invention also provides a catalytic system for the aryl halide coupling reaction. Thecatalytic system comprises a copper catalyst, a compound containing a 2-(substituted or non-substituted) aminopyridine nitrogen-oxygen group adopted as a ligand, alkali and a solvent, and meanwhile, the invention also provides a system for the aryl halide coupling reaction adopting the catalyst system. The compound containing the 2-(substituted or non-substituted) aminopyridine nitrogen oxygen group can be used as the ligand for the copper catalyzed aryl chloride coupling reaction, and the ligand is stable under a strong alkaline condition and can well maintain catalytic activity when being used for the copper-catalyzed aryl chloride coupling reaction. In addition, the copper catalyst adopting the compound as the ligand can particularly effectively promote coupling of copper catalyzed aryl chloride and various nucleophilic reagents which are difficult to generate under conventional conditions, C-N, C-O and C-S bonds are generated, and numerous useful small molecule compounds are synthesized. Therefore, the aryl halide coupling reaction has a very good large-scale application prospect by adopting the copper catalysis system of the ligand.
Method for preparing amino compound by catalytically reducing nitro compound with alkaline earth metal hydride
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Paragraph 0074-0077, (2020/09/16)
The invention relates to a method for preparing an amino compound by catalytically reducing a nitro compound with alkaline earth metal hydride, and belongs to the technical field of organic synthesis.The method comprises the following steps: by taking a nitro compound as a reaction substrate, alkaline earth metal hydride as a hydrogen source and diborate as a catalyst, respectively adding the nitro compound, the alkaline earth metal hydride and the diborate into an organic solvent, stirring and heating to react for 3-20 hours at the reaction temperature of 50-150 DEG C; and after the reactionis finished, separating and purifying the reaction mother liquor to obtain the amino compound. The method has the advantages of simple synthesis steps, mild reaction conditions, avoiding of the use of high pressure hydrogen, no participation of transition metals in the reaction process, reduction of the reaction cost, greenness, environmental protection, and reduction of the environmental pollution.
Diverse Oxidative C(sp2)-N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides
Xu, Fangzhou,Wang, Yanyan,Xun, Xiwei,Huang, Yun,Jin, Zhichao,Song, Baoan,Wu, Jian
, p. 8411 - 8422 (2019/05/17)
An efficient and chemoselective C(sp2)-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as α-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some α-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.
Synthesis of N-aryl and N-heteroaryl hydroxylamines via partial reduction of nitroarenes with soluble nanoparticle catalysts
Tyler, Jefferson H.,Nazari, S. Hadi,Patterson, Robert H.,Udumula, Venkatareddy,Smith, Stacey J.,Michaelis, David J.
supporting information, p. 82 - 86 (2016/12/23)
Polystyrene-supported ruthenium nanoparticles enable the selective hydrazine-mediated reduction of nitroarenes to hydroxylamine products in high yield and selectivity. Key to obtaining the hydroxylamine product in good yield was the use of organic solvents capable of solubilizing the polystyrene-supported nanoparticle catalyst. N-aryl and N-heteroaryl hydroxylamines are generated under exceptionally mild conditions and in the presence of a various easily reduced functional groups.
Boron Lewis Acid Promoted Ruthenium-Catalyzed Hydrogenation of Amides: An Efficient Approach to Secondary Amines
Yuan, Ming-Lei,Xie, Jian-Hua,Zhou, Qi-Lin
, p. 3036 - 3040 (2016/10/11)
The hydrogenation of amides to amines has been developed by using the catalyst [Ru(H)2(CO)(Triphos)] (Triphos=1,1,1-tri(diphenylphosphinomethyl)ethane) and catalytic boron Lewis acids such as B(C6F5)3 or BF3?Et2O as additives. The reaction provides an efficient method for the preparation of secondary amines from amides in good yields with high selectivity.
Tertiary formylated amines by microwave irradiation of N,N-dimethyl- N′-(2-pyridyl) formamidines with methyl vinyl ketone
Gomez-Garcia, Omar,Salgado-Zamora, Hector,Campos-Aldrete, Elena
, p. 21 - 23 (2014/04/03)
Treatment of N,N-dimethyl-N′-(2-pyridyl)formamidine with methyl vinyl ketone under microwave irradiation yields N-formyl-N-(3-oxobutyl)-2- pyridylamine without decomposition or polymerization of methyl vinyl ketone. The result is an alternative non-oxidat
