106942-26-1Relevant academic research and scientific papers
Rapid assembly of α-ketoamides through a decarboxylative strategy of isocyanates with α-oxocarboxylic acids under mild conditions
Huang, Junjie,Liang, Baihui,Chen, Xiuwen,Liu, Yifu,Li, Yawen,Liang, Jingwen,Zhu, Weidong,Tang, Xiaodong,Li, Yibiao,Zhu, Zhongzhi
, p. 4783 - 4787 (2021/06/11)
A simple and practical method for α-ketoamide synthesis via a decarboxylative strategy of isocyanates with α-oxocarboxylic acids is described. The reaction proceeds at room temperature under mild conditions without an oxidant or an additive, showing good substrate scope and functional compatibility. Moreover, the applicability of this method was further demonstrated by the synthesis of various bioactive molecules and different application examples through a two-step one-pot operation.
“On-water” reduction of α-keto amide by Hantzsch ester: A chemoselective catalyst- and additive-free way to α-hydroxy amide
Fang, Zhong-Bing,Yu, Ru-Rong,Hao, Fei-Yue,Jin, Zheng-Neng,Liu, Gu-Yue,Dai, Guo-Liang,Yao, Wu-Bing,Wu, Jia-Shou
supporting information, (2021/11/18)
An efficient and practical method for chemoselective “on-water” reduction of α-keto amide by Hantzsch ester without using any catalysts and additives was developed. Control experiments indicated that the intramolecular hydrogen bond of α-keto amide was cr
Ru-g-C3N4as a highly active heterogeneous catalyst for transfer hydrogenation of α-keto amide into β-aminol or α-hydroxyl amide
Bhanage, Bhalchandra M.,Chaurasia, Shivkumar R.,Mishra, Ashish A.
, p. 10578 - 10585 (2020/07/14)
This work reports a sustainable route for the catalytic transfer hydrogenation (CTH) of α-keto amide into β-aminol via an efficient heterogeneous catalyst wherein ruthenium is incorporated on an active graphite sheet of a carbon nitride support (Ru-g-C3N4). Other different metals like Ni or Pd were also screened with the same support but none of them showed efficient activity. Although, partial hydrogenation of ketone to alcohol has also been observed based on the optimization of the reaction parameters using all of the above catalysts. The catalyst has been characterized using field emission gun scanning electron microscopy (FEG-SEM), X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), infra-red (IR) spectroscopy and thermogravimetric analysis (TGA). Furthermore, the catalyst has been recycled and further characterized and does not show any significant changes in its reactivity for the CTH process. Ru-g-C3N4 as a recyclable heterogenous catalyst has been used for the first time for the CTH of α-keto amide into β-aminol, making the process sustainable because economical and environmentally benign isopropyl alcohol is used as a solvent system. The proposed catalytic system shows a wide scope of substrates for α-hydroxyamide and β-aminol derivatives, which were confirmed from 1H and 13C-NMR. This journal is
Catalyst- and Additive-Free Chemoselective Transfer Hydrogenation of α-Keto Amides to α-Hydroxy Amides by Sodium Formate
Hao, Feiyue,Gu, Zhenyu,Liu, Guyue,Yao, Wubing,Jiang, Huajiang,Wu, Jiashou
, p. 5985 - 5991 (2019/09/10)
A catalyst- and additive-free chemoselective transfer hydrogenation of α-keto amides to α-hydroxy amides is easily achieved by using sodium formate as a hydrogen source. The utility of this method is demonstrated by gram-scale synthesis and transformation of the resultant α-hydroxy amides into polysubstituted acetamides and 2-arylindole derivatives. Control experiments suggest that the NH group of α-keto amides is crucial for the chemoselective reduction through the formation of hydrogen bonds.
Zirconium-MOF-catalysed selective synthesis of α-hydroxyamide via the transfer hydrogenation of α-ketoamide
Mishra, Ashish A.,Bhanage, Bhalchandra M.
, p. 6160 - 6167 (2019/04/25)
This work reports the synthesis of α-hydroxy amide and its derivatives using zirconium-based metal-organic frameworks (Zr-MOFs). The Zr-MOF was prepared using a ligand containing different functionalities as a linker with different porosities. The catalyst efficiently facilitated the transfer hydrogenation of α-ketoamide to α-hydroxyamide. The reaction involved a green hydrogen source, namely isopropyl alcohol, which also acted as a solvent. The role of the ligand in the catalyst was optimized for the selective conversion of α-ketoamide to α-hydroxyamide. UiO-66 (Zr) crystal was efficiently used for the first time for the hydrogenation of α-ketoamide to α-hydroxyamide. The catalyst was recovered and recycled five times without any loss in activity and selectivity performance. The morphology, activity and stability of the UiO-66 (Zr) catalyst were analyzed using field emission gun scanning electron microscopy (FEG-SEM), X-ray diffraction (XRD), infra-red (IR) spectroscopy and thermogravimetric analysis (TGA). The existence of α-hydroxyamide and its derivatives was confirmed from 1H and 13C-NMR.
A Mild and Chemoselective Hydrosilylation of α-Keto Amides by Using a Cs2CO3/PMHS/2-MeTHF System
Kumar, Govindharaj,Muthukumar, Alagesan,Sekar, Govindasamy
, p. 4883 - 4890 (2017/09/13)
A Cs2CO3-catalyzed hydrosilylation reaction of α-keto amides that proceeds through the in situ formation of MeSiH3 has been developed by using inexpensive polymethylhydrosiloxane in 2-methyltetrahydrofuran (2-MeTHF) as the solvent. A wide range of aryl and alkyl α-keto amides, prepared from anilines and alkylamines, were subjected to the hydrosilylation conditions to afford α-hydroxy amides in moderate to excellent yields. This transition-metal-free protocol was applied to a chemoselective hydrosilylation, in which reduction occurred at the carbonyl of the α-keto amide functionality over that of the simple ketone, and further extended to a gram-scale protocol.
Potassium Phosphate-Catalyzed Chemoselective Reduction of α-Keto Amides: Route to Synthesize Passerini Adducts and 3-Phenyloxindoles
Muthukumar, Alagesan,Mamillapalli, N. Chary,Sekar, Govindasamy
, p. 643 - 652 (2016/02/27)
A chemoselective reduction of α-keto amides to biologically important α-hydroxy amides (mandelamides) by polymethylhydrosiloxane (PMHS) using 5 mol% potassium phosphate (K3PO4) as catalyst has been developed. This transition metal-free protocol discloses excellent chemoselectivity for the ketone reduction of α-keto amides in the presence of other reducible functionalities like ketone, nitro, halides, nitrile and amide. Also, the chemoselectively reduced α-hydroxy amide has been derivatized to isocyanide-free Passerini adducts. The N-alkyl-α-hydroxy amides have been successfully converted to 3-phenyloxindole derivatives by treatment with methanesulfonyl cholride and triethylamine.
Α-hydroxy aryl acetylmethylene aromatic amine synthesis process
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Paragraph 0008; 0009, (2016/10/10)
Alpha-hydroxy aryl acetyl arylamine can be used as medicine and organic intermediate. The invention discloses a synthetic process of alpha-hydroxy aryl acetyl arylamine. Under existence of a copper catalyst and alkali, alpha-hydroxy aryl acetamide and ary
Amidation of Carboxylic Acids with Amines by Nb2O5 as a Reusable Lewis Acid Catalyst
Ali,Siddiki,Onodera, Wataru,Kon, Kenichi,Shimizu, Ken-Ichi
, p. 3555 - 3561 (2015/11/10)
Among 28 types of heterogeneous and homogenous catalysts tested, Nb2O5 shows the highest yield for direct amidation of n-dodecanoic acid with a less reactive amine (aniline). The catalytic amidation by Nb2O5 is applicable to a wide range of carboxylic acids and amines with various functional groups, and the catalyst is reusable. A comparison of the results of the catalytic study and an infrared study of the acetic acid adsorbed on the catalyst suggests that activation of the carbonyl group of the carboxylic acid by Lewis acid sites on Nb2O5 is responsible for the high activity of the Nb2O5 catalyst. Kinetic studies show that Lewis acid sites on Nb2O5 are more water-tolerant than conventional Lewis acidic oxides (Al2O3, TiO2). In comparison with the state-of-the-art homogeneous Lewis acid catalyst for amidation (ZrCl4), Nb2O5 undergoes fewer negative effects from basic additives in the solution, which indicates that Nb2O5 is a more base-tolerant Lewis acid catalyst than the homogeneous Lewis acid catalyst.
Synthesis of α-Hydroxycarboxylic Acid Anilides via Copper-Catalyzed C-N Coupling of α-Hydroxyamides with Aryl Halides
Li, Zhijie,Wen, Quan,Zhou, Lihong,Deng, Xingmei,Zeng, Qingle
supporting information, p. 3751 - 3757 (2015/11/28)
The synthesis of highly important α-hydroxycarboxylic acid anilides via copper-catalyzed chemoselective C-N coupling reactions of α-hydroxyamides and aryl halides is described. This highly selective N-arylation process demonstrates wide substrate scope, c
