60375-56-6Relevant articles and documents
Tetrasubstituted 1,3-Enynes by Gold-Catalyzed Direct C(sp2)-H Alkynylation of Acceptor-Substituted Enamines
Han, Chunyu,Tian, Xianhai,Zhang, Huili,Rominger, Frank,Hashmi, A. Stephen K.
supporting information, p. 4764 - 4768 (2021/06/30)
A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp2)-H functionalization of alkenes, offering 26 enynes in 62-92% yield with excellent functional group tolerance.
Green synthesis method of nicotinic acid ester compounds based on non-metallic conditions
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Paragraph 0058; 0061, (2021/09/29)
The invention discloses a green synthesis method based on nicotinic acid ester compounds under non-metallic conditions, and belongs to the technical field of organic synthesis. The method comprises the following steps of (III) replacing cyclopropanol and (II) substituted enamine ester as a raw material, taking tetramethyl piperidine nitrogen oxide as an oxidizing agent, 110 - 130 °C, stirring and reacting in an organic solvent to synthesize a (I) nicotinate compound. The invention provides a green synthesis method based on nicotinic acid ester compounds under non-metallic conditions, wherein cyclopropanols and enamine esters are taken as raw materials, and a polysubstituted nicotinate is synthesized through a strategy of oxidative dehydrogenation of ketene cyclization.
Multi-component synthesis of 3-substituted indoles and their cyclisation to α-carbolines: Via I2-promoted intramolecular C2 oxidative amination/aromatisation at room temperature
Deka, Bhaskar,Baruah, Pranjal K.,Deb, Mohit L.
supporting information, p. 7806 - 7810 (2018/11/21)
Condensation of indoles, aldehydes and pyrazol-5-amine in the presence of ceric ammonium nitrate gives 3-substituted indoles. These then cyclise to α-carbolines at room temperature through I2-promoted intramolecular C2 amination and aromatisation in open air. A plausible mechanism is proposed based on some controlled experiments.
Synthesis of trifluoromethylated 2H-azirines through Togni reagent-mediated trifluoromethylation followed by PhIO-mediated azirination
Sun, Jiyun,Zhen, Xiaohua,Ge, Huaibin,Zhang, Guangtao,An, Xuechan,Du, Yunfei
supporting information, p. 1452 - 1458 (2018/07/05)
The reaction of enamine compounds with the Togni reagent in the presence of CuI afforded β-trifluoromethylated enamine intermediates, which were converted directly to biologically interesting trifluoromethylated 2H-azirines by an iodosobenzene (PhIO)-mediated intramolecular azirination in a one-pot process.
Tandem Thorpe Reaction/Palladium Catalyzed Asymmetric Allylic Alkylation: Access to Chiral β-enaminonitriles with Excellent Enantioselectivity
Bai, Da-Chang,Liu, Xiu-Yan,Li, Hao,Ding, Chang-Hua,Hou, Xue-Long
, p. 212 - 215 (2017/02/05)
A new type of nucleophile, a 3-imino nitrile carbanion generated in situ by Thorpe reaction of acetonitrile with a base, was developed successfully and applied in a Pd-catalyzed asymmetric allylic alkylation with mono-substituted allyl reagents under Pd/S
In situ click chemistry generation of cyclooxygenase-2 inhibitors
Bhardwaj, Atul,Kaur, Jatinder,Wuest, Melinda,Wuest, Frank
, (2017/03/08)
Cyclooxygenase-2 isozyme is a promising anti-inflammatory drug target, and overexpression of this enzyme is also associated with several cancers and neurodegenerative diseases. The amino-acid sequence and structural similarity between inducible cyclooxygenase-2 and housekeeping cyclooxygenase-1 isoforms present a significant challenge to design selective cyclooxygenase-2 inhibitors. Herein, we describe the use of the cyclooxygenase-2 active site as a reaction vessel for the in situ generation of its own highly specific inhibitors. Multi-component competitive-binding studies confirmed that the cyclooxygenase-2 isozyme can judiciously select most appropriate chemical building blocks from a pool of chemicals to build its own highly potent inhibitor. Herein, with the use of kinetic target-guided synthesis, also termed as in situ click chemistry, we describe the discovery of two highly potent and selective cyclooxygenase-2 isozyme inhibitors. The in vivo anti-inflammatory activity of these two novel small molecules is significantly higher than that of widely used selective cyclooxygenase-2 inhibitors.
Acid-promoted rapid solvent-free access to substituted 1,4-dihydropyridines from β-ketothioamides
Li, Ming,Sun, Ke-Na,Wen, Li-Rong
, p. 21535 - 21539 (2016/03/08)
β-Ketothioamides (KTAs) have been used as building blocks with aldehydes and β-enaminonitriles for synthesis of 1,4-dihydropyridines in the presence of AcOH under solvent-free conditions within 5 min. This new strategy exhibits remarkable features such as high chemoselectivity, mild reaction conditions, easily available substrates, and good yields.
Enantioselective biocatalytic hydrolysis of β-aminonitriles to β-amino-amides using Rhodococcus rhodochrous ATCC BAA-870
Chhiba, Varsha,Bode, Moira L.,Mathiba, Kgama,Kwezi, Wendy,Brady, Dean
experimental part, p. 68 - 74 (2012/04/10)
A range of β-aminonitriles (3-amino-3-phenylpropanenitrile and derivatives) were synthesised by reaction of various benzonitriles with acetonitrile and subsequent reduction of the resulting acrylonitrile products. These compounds were hydrolysed to the co
Rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylonitriles
Ma, Miaofeng,Hou, Guohua,Wang, Junru,Zhang, Xumu
experimental part, p. 506 - 511 (2011/06/17)
The rhodium-catalyzed asymmetric hydrogenation of β-acetylamino acrylonitriles was investigated by using monophosphine and bisphosphine ligands. It was found that an Rh-QuinoxP complex exhibited high enantioselectivities for β-aryl substituted β-acetylamino acrylonitriles and the Rh-JosiPhos CyPF-t-Bu complex was proven to be effective for the hydrogenation of tetrasubstituted olefins from cyclic β-acetylamino acrylonitriles.
Design and synthesis of substituted N-(1,3-diphenyl-1H-pyrazol-5-yl) benzamides as positive allosteric modulators of the metabotropic glutamate receptor subtype 5
Zou, Mu-Fa,Cao, Jianjing,Rodriguez, Alice L.,Jeffrey Conn,Newman, Amy Hauck
scheme or table, p. 2650 - 2654 (2011/06/20)
Based on SAR in the alkyne class of mGlu5 receptor negative allosteric modulators and a set of amide-based positive allosteric modulators, optimized substitution of the aryl bring was used to create substituted N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides.
