24301-97-1Relevant academic research and scientific papers
Aqueous CO2fixation: construction of pyridine skeletons in cooperation with ammonium cations
Fan, Weibin,Guo, Shiwei,Huang, Deguang,Li, Yinghua,Xiang, Shiqun,Zhang, Wei
supporting information, p. 7950 - 7955 (2021/10/29)
A simple and green method is explored for the synthesis of fused pyridines by [2 + 2 + 1 + 1] the cycloaddition of ketones with an ammonium cation under a CO2atmosphere. The reactions employed ammonium cation as a nitrogen source and CO2gas as a carbon source in an aqueous solution. Monoethanolamine (MEA) was used as an additive to increase the solubility of CO2in an aqueous solution. The scope and versatility of the method are demonstrated with 38 examples. Products are found to be photosensitive and show potential applications as organic optoelectronic materials. A selectfluor-promoted reaction mechanism is proposed based on the experimental studies. Our work is superior as it is a metal-free system, uses CO2as a carbon source and MEA as an additive in aqueous synthesis.
Sustainable Four-Component Annulation for the Synthesis of 2,3,4,6-Tetraarylpyridines
Ding, Yuxin,Ma, Renchao,Xiao, Xu-Qiong,Wang, Lei,Wang, Zhiming,Ma, Yongmin
, p. 3897 - 3906 (2021/03/09)
A one-pot, four-component annulation of 2,3,4,6-tetraarylpyridines from aromatic aldehydes, methyl ketones, diaryl ethanones, and ammonium acetate is described. The reaction features high functional group compatibility in air under solvent-free conditions without any additive and only water as the nontoxic byproduct, providing a strategy for the facile, economical, and eco-friendly construction of multiaryl-substituted pyridines from simple and readily available reactants.
A Method to Access Symmetrical Tetrasubstituted Pyridines via Iodine and Ammonium Persulfate Mediated [2+2+1+1]-Cycloaddition Reaction
Liu, Weibing,Tan, Hua,Chen, Cui,Pan, Yupeng
supporting information, p. 1594 - 1598 (2017/05/05)
A novel metal-free [2+2+1+1]-cycloaddition method for rapid and productive preparation of symmetrical 2,3,5,6-tetrasubstituted pyridines has been developed from α-substituted arones and N,N-dimethyl formamide (DMF) using iodine (I2) and ammonium persulfate ((NH4)2S2O8) as mediators. In this process, both DMF and (NH4)2S2O8 play a dual role for the formation of pyridines. DMF acts as the reaction medium and the C4 source (the methyl group of DMF), while (NH4)2S2O8 serves as the oxidant and nitrogen resource. Notably, this transformation exhibited a broad substrate scope towards a wide variety of different arones to give the corresponding tetrasubstituted pyridines in moderate to excellent yields. (Figure presented.).
Synthesis of tetraarylpyridines by chemo-selective Suzuki-Miyaura reactions of 3,5-dibromo-2,6-dichloropyridine
Reimann, Sebastian,Parpart, Silvio,Ehlers, Peter,Sharif, Muhammad,Spannenberg, Anke,Langer, Peter
, p. 6832 - 6838 (2015/06/25)
Chemoselective Suzuki-Miyaura reactions on 3,5-dibromo-2,6-dichloropyridine were studied. The optimized reaction conditions allow for the facile access of 3-aryl- and 3,5-diarylpyridines in good yields. Suzuki-Miyaura reactions of the selectively synthesi
Site-selective synthesis of arylated pyridines by Suzuki-Miyaura reactions of 2,3,5,6-tetrachloropyridine
Reimann, Sebastian,Ehlers, Peter,Parpart, Silvio,Surkus, Annette,Spannenberg, Anke,Langer, Peter
supporting information, p. 5371 - 5384 (2015/07/15)
Site-selective arylation of commercially available 2,3,5,6-tetrachloropyridine has been accomplished, using the Suzuki-Miyaura reaction. The reaction conditions were thoroughly optimized, allowing the selective synthesis of mono-, di-, tri- and tetraarylated pyridines in good to quantitative yields. In addition, we studied the electrochemical properties of selected tetraarylpyridines by DPV-measurements.
Ruthenium-catalyzed cyclization of ketoxime acetates with DMF for synthesis of symmetrical pyridines
Zhao, Mi-Na,Hui, Rong-Rong,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 3082 - 3085 (2014/06/23)
A novel ruthenium-catalyzed cyclization of ketoxime carboxylates with N,N-dimethylformamide (DMF) for the synthesis of tetrasubstituted symmetrical pyridines has been developed. A methyl carbon on DMF performed as a source of a one carbon synthon. And NaHSO3 plays a role in the reaction.
Simple selective synthesis of 2,4- and 2,6-diarylpyridines through metal-free cyclocondensation of aromatic ketones with ammonium acetate
Liu, Jin,Wang, Chuanxin,Wu, Liansheng,Liang, Fen,Huang, Guosheng
experimental part, p. 4228 - 4234 (2011/02/22)
A simple and selective one-pot synthesis of 2,4- and 2,6-diarylpyridines through the cyclocondensation reaction of aromatic ketones with ammonium acetate has been developed. The procedure is metal-free, convenient, and efficient, and the substrates are re
The Reaction of (Z)-2-(3-Oxo-1-propenyl)-2H-azirine Derivative with Molybdenum Carbonyl Complexes
Kobayashi, Tomoshige,Nitta, Makoto
, p. 1057 - 1058 (2007/10/02)
The thermal reaction of (Z)-2,3-diphenyl-2-(2,3-diphenyl-3-oxo-1-propenyl)-2H-azirine with or was reinvestigated to afford 2,3,5,6-tetraphenylpyridine along with the pyrroles and 1,3-oxazepine derivative.The formation of 1,3-oxa
ETUDE DE LA REACTIVITE DE L'ION AZTURE VIS A VIS DE CATIONS HETEROCYCLIQUES-III REARRANGEMENTS THERMIQUES ET PHOTOCHIMIQUES DES AZIDES COVALENTS RESULTANT DE L'ION AZOTURE SUR DES CATIONS PYRYLIUM ET THIOPYRYLIUM DIVERSEMENT SUBSTITUES. NOUVEL ACCES A DES HETEROAZEPINES
Desbene, P.-L.,Cherton, J.-C.
, p. 3559 - 3565 (2007/10/02)
Azidopyrans rearrange at room temperature to 1,3-oxazepins but azidothiopyrans need heating to form unstable thiazepins. these intermediate thiazepins give the competitive formation of the corresponding pyridines after sulphur extrusion or of the corresponding thiophens after elimination of benzonitrile. Photochemical attempts to obtain thiazepins from azidothiopyrans were unsuccessful.
Kinetics and Mechanism of the C-Alkylation of Nitroalkane Anions by 1-Alkyl-2,4,6-triphenylpyridiniums: A Nonchain Reaction with Radicaloid Characteristics
Katritzky, Alan R.,Kashmiri, M. Akram,Ville, George Z. de,Patel, Ranjan C.
, p. 90 - 96 (2007/10/02)
The C-alkylation of 2-nitropropanide by N-substituted pyridiniums is first order in each reactant in Me2SO.The effect on the rate of temperature , N substituent, leaving group, and nucleophile was studied quantitatively.Overall, the evidence excludes an SN2 displacement and suggests that the reactions proceed by a free radical nonchain mechanism.
