59803-39-3Relevant academic research and scientific papers
A substituted cyano acetate preparation method (by machine translation)
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Paragraph 0022-0039; 0047, (2017/05/19)
The invention discloses a substituted cyano acetate preparation method, characterized in that comprises the following steps: (I) takes the aldehyde class compound, cyano acetic acid esters (II) and (III) dihydro pyridine ester, uses water as solvent, mixe
Solvent-free preparation method for substituted cyanoacetate compound
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Paragraph 0027; 0033-0035, (2018/02/04)
The invention discloses a solvent-free preparation method for a substituted cyanoacetate compound. The method is characterized by comprising the following steps: subjecting an aldehyde compound (I) represented by a formula shown in the description, cyanoacetate (II) represented by a formula shown in the description and a dihydropyridine ester (III) represented by a formula shown in the description to a hybrid reaction under solvent-free conditions, and carrying out separation and purification after the reaction is completed, thereby obtaining the substituted cyanoacetate (IV) represented by a formula shown in the description. According to the method, aldehydes, cyanoacetate and dihydropyridine esters serve as raw materials for the first time, and the substituted cyanoacetate can be efficiently synthesized through a one-pot method reaction without solvents and catalysts, so that the preparation method is simple, efficient and environmentally friendly.
Base-Promoted Cascade Approach for the Preparation of Reduced Knoevenagel Adducts Using Hantzsch Esters as Reducing Agent in Water
He, Tao,Shi, Ronghua,Gong, Yimou,Jiang, Guangyou,Liu, Ming,Qian, Shan,Wang, Zhouyu
supporting information, p. 1864 - 1869 (2016/07/16)
A cascade Knoevenagel condensation-reduction approach, which was carried out in water, has been reported. Using Hantzsch esters as reducing agent, under the promotion of base, a variety of reduced Knoevenagel adducts could be easily prepared by direct alkylation of malononitrile, ethyl 2-cyanoacetate, and 2-(4-nitrophenyl)acetonitrile, respectively. Meanwhile, a gram-scale synthesis of the protocol was also realized with excellent isolated yield.
One-pot approach for C-C bond formation through ruthenium-amido complex catalyzed tandem aldol reaction/hydrogenation
Sun, Haifeng,Ye, Deju,Jiang, Hualiang,Chen, Kaixian,Liu, Hong
supporting information; experimental part, p. 2577 - 2582 (2010/09/05)
A one-pot novel and efficient approach was developed for the -alkylation of various nitriles with carbonyl compounds using ruthenium-amido complex catalyst 1. The C-C bond was formed through aldol reaction followed by hydrogenation with triethylamine-formic acid (TEAF) and 1. Moderate to high yields were obtained, and a variety of functional groups were tolerated, including nitro and chloro groups, and a furan ring. Georg Thieme Verlag Stuttgart New York.
Development of pharmaceutical drugs, drug intermediates and ingredients by using direct organo-click reactions
Ramachary, Dhevalapally B.,Kishor, Mamillapalli,Reddy, Y. Vijayendar
supporting information; experimental part, p. 975 - 993 (2009/04/11)
Here we report on our studies of the use of combinations of amino acids, amines, K2CO3 or Cs2CO3 and CuSO4/Cu for catalysing green cascade reactions. We aimed to prepare the highly reactive and substituted olefin species 7 and 8, under very mild and environmentally friendly conditions, thus giving the hydrogenated products 10 and 12 through the action of Hantzsch ester (4) by self-catalysis through decreasing the HOMO-LUMO energy gaps between olefins 7/8 and Hantzsch ester (4) through biomimetic reductions. Highly useful compounds 10 to 14 were assembled from simple substrates such as aldehydes 1, ketones 2, CH acids 3, Hantzsch ester (4) and alkyl halides 5 by diversity-oriented green synthesis involving cascade olefination/hydrogenation (O/H), olefination/hydrogenation/alkylation (O/H/A) and hydrogenation/olefination/hydrogenation (H/O/H) reaction sequences in one-pot fashion with stereospecific organo- and organo-/metal-carbonate catalysis. Highly functionalized diverse compounds such as 10 to 14 are biologically active products and have found wide applications as pharmaceutical drugs, drug intermediates and drug ingredients. For the first time in organocatalysis, we report the O/H/A/TE reaction to furnish high yields of transesterification products 11 by simply mixing the reactants under proline/K2CO3 catalysis conditions. Additionally, a novel organocatalytic H/O/H reaction sequence for the synthesis of alkyl-substituted aromatics has been developed. Furthermore, for the first time we have developed organocatalysed cascade olefination/hydrogenation/hydrolysis (O/H/H) reactions to furnish highly useful materials such as 2-oxochroman-3-carboxylic acid (14kc) and 2-amino-4H-chromene-3-carbonitrile (14kj) in good yields. Experimentally simple and environmentally friendly organocatalytic two-carbon homologation through cascade O/H/H reactions of aldehydes 1, Meldrum's acid (3c), Hantzsch ester (4) and acetic acid/triethylamine in ethanol has been demonstrated. Additionally, we have developed a green synthesis of the highly substituted 1,2,3-triazole 17 from simple substrates through a two-step combination of olefination/hydrogenation/alkylation and Huisgen cycloaddition reaction sequences under stereospecific organocopper catalysis conditions. In this paper we have found strong support for our hypothesis that, "decreasing the HOMO-LUMO energy gap between olefins 7/8 and Hantzsch ester (4) will drive the biomimetic hydrogenation reaction by self-catalysis". This self-catalysis was further confirmed with many varieties of examples. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
