1127405-07-5Relevant academic research and scientific papers
Preparation method of alpha-carbonyl amide compound
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Paragraph 0106-0109, (2021/08/14)
The invention discloses a preparation method of an alpha-carbonyl amide compound. The method comprises the following steps: under the action of a catalyst, taking oxygen as an oxidant, and carrying out oxidative amidation reaction on an alpha-diazoketone compound shown in a chemical formula 2 and a cyclic secondary amine compound shown in a chemical formula 3 in an organic solvent to obtain the alpha-carbonyl amide compound shown in a chemical formula 1, wherein the formulas 1, 2 and 3 are also shown in the speification. According to the preparation method disclosed by the invention, the alpha-carbonyl amide compound is obtained by taking oxygen as the oxidizing agent and catalyzing alpha-diazoketone and cyclic secondary amine to be subjected to oxidative amidation reaction through cuprous iodide, the reaction condition is mild, the reaction time is short, and the byproduct of the reaction is only nitrogen, so that the method is an effective way for green and efficient preparation of the alpha-carbonyl amide compound.
Cu(OAc)2 and acids promoted the oxidative cleavage of α-aminocarbonyl compounds with amines: efficient and selective synthesis of 2-t-amino-2-imino-carbonyl and 2-amino-2-oxocarbonyl
Chen, De,Cheng, Chaozhihui,Zeng, Sheng,Luo, Yongyue,Zhang, Jiajia,Deng, Wei,Zeng, Zebing,Wang, Ruijia,Xiang, Jiannan
supporting information, (2020/04/15)
A novel and efficient method for the synthesis of 2-t-amino-2-imino-carbonyl (C) and 2-amino-2-oxocarbonyl (D) compounds has been discovered through a copper-promoted oxidating amidation reactions between α-amino -carbonyl compounds and amines. Promoted by the crucial copper species, perfect selectivity and good to excellent yields could be achieved. This transformation is achieved through C[sbnd]N bond oxidative cleavage and formation a novel C[sbnd]N bond. This reaction system has a broad reaction scope, providing a facile pathway for the α-functionalization of α-amino ketones.
Cu-Catalyzed aerobic oxidative cleavage of C(sp3)–C(sp3) bond: Synthesis of α-ketoamides
Fang, Zheng,Guo, Kai,Liu, Chengkou,Yang, Man,Zhang, Jingming
supporting information, (2020/11/02)
A novel synthesis of α-ketoamides from Cu-catalyzed aerobic oxidative C(sp3)–C(sp3) bond cleavage of hydrocinnamaldehydes has been developed. Readily available and environmentally benign oxygen is used as the oxidant. This reaction avoids the use of noble metal catalysts or specialized oxidants, and chemoselectively yields α-ketoamide. Moreover, based on various control experiments, a reasonable mechanism is proposed.
Double carbonylation of iodoarenes in the presence of a pyridinium SILP-Pd catalyst
Nagy, Enik?,Nagy, Petra,Papp, Máté,Skoda-F?ldes, Rita,Urbán, Béla
, (2020/04/28)
The efficiency of a palladium catalyst, immobilised on a supported ionic liquid phase (SILP) with adsorbed 1-butyl-4-methylpyridinium chloride, was investigated in aminocarbonylation reactions. Double carbonylation was found to be the main reaction using different iodoarenes and aliphatic amines as substrates. Application of aniline derivatives as nucleophiles led to the exclusive formation of substituted benzamides. The stabilisation effect of the adsorbed pyridinium ionic liquid was compared to that of imidazolium and phosphonium derivatives. It was proved that the pyridinium SILP-palladium catalyst could be reused in at least 10 cycles. Recyclability was tested in five successive runs for all of the substrates.
POP-Pd(ii) catalyzed easy and safe: In situ carbonylation towards the synthesis of α-ketoamides from secondary cyclic amines utilizing CHCl3 as a carbon monoxide surrogate
Islam, Sk Safikul,Riyajuddin, Sk,Molla, Rostam Ali,Yasmin, Nasima,Ghosh, Kaushik,Islam, Sk. Manirul
, p. 1979 - 1987 (2020/02/13)
A novel complex catalyst, POP-palladium(ii), has been synthesized. The developed catalyst has been characterized by XRD, EDX, scanning electron microscopy (FE-SEM), HR-TEM, FTIR spectroscopy, UV-vis spectroscopy, TGA and BET isotherm analysis. The reactiv
Metal-Free C=C Double Bond Cleavage on Enaminones for the Synthesis of α-Ketoamides by Free-Radical Aerobic Oxygenation
Yang, Yiming,Zhong, Guofeng,Fan, Junfen,Liu, Yunyun
supporting information, p. 4422 - 4425 (2019/06/24)
The tandem oxidation of the enaminone C=C double bond as well as subsequent C-N bond formation are realized under metal-free conditions by thermo-induced free radical transformation. In the presence of benzoyl peroxide (BPO) and N-iodosuccinimide (NIS), a
Cu-Catalysed oxidative amidation of cinnamic acids/arylacetic acids with 2° amines: An efficient synthesis of α-ketoamides
Sharma, Anup Kumar,Jaiswal, Anjali,Singh, Krishna Nand
supporting information, p. 9348 - 9351 (2019/11/11)
A new and convenient copper-catalysed synthesis of α-ketoamides has been accomplished using readily available cinnamic acids/arylacetic acids and 2° amines in an open atmosphere. The reaction between cinnamic acid and amine involves the formation of enamine followed by its aerobic oxidation, whereas the reaction of arylacetic acid with amine involves amide formation followed by benzylic methylene oxidation.
Copper-catalyzed oxidative synthesis of 2-oxo-acetamidines from one-pot three-component reaction of aryl methyl ketones, secondary amines and anilines
Dutta, Leema,Bhuyan, Pulak J.
, p. 5770 - 5778 (2018/08/22)
Some novel 2-oxo-acetamidines were synthesized via one-pot three-component reaction of acetophenones, secondary amines and anilines in presence of CuI as catalyst. The reaction involved in a oxidation process of C (sp3)–H bonds of acetophenones
UV Assisted High-Efficient Synthesis of α-Ketoamides using Air Promoted by A Non-Metal Catalyst in Aqueous Solution
Li, Jianhui,He, Shaopo,Zhang, Kuan,Quan, Ziyi,Shan, Qiheng,Sun, Zhongliang,Wang, Bo
, p. 4868 - 4873 (2018/10/15)
Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α-ketoamides of all types using a non-metal catalyst N-iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.?), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary-, secondary-, and tertiary α-ketoamides were afforded in good to excellent yields of up to 96 %.
