938-73-8Relevant articles and documents
Method for preparing primary and secondary amide compounds
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Paragraph 0068-0078, (2021/02/06)
The invention belongs to the field of organic chemical synthesis, and particularly relates to a method for preparing primary and secondary amide compounds. The method for preparing primary and secondary amide compounds comprises the following steps of carrying out catalytic reduction on an N-substituted amide compound at 30-130 DEG C by using a protic solvent as a reduction reagent and a dichloro(p-methyl isopropylbenzene) ruthenium (II) dimer complex as a catalyst to obtain a reaction solution after the reduction reaction is finished, and carrying out post-treatment on the reaction solution to obtain the corresponding primary amide compound or secondary amide compound. According to the method for preparing the primary and secondary amide compounds, the transfer hydrogenation reaction of nitrogen-oxygen and nitrogen-carbon bonds is realized, the reaction conditions are mild and simple, the substrate application range is wide, the operation is convenient, and the corresponding primary amide compound or secondary amide compound is obtained with high efficiency and high selectivity.
Ti-superoxide catalyzed oxidative amidation of aldehydes with saccharin as nitrogen source: Synthesis of primary amides
Kamble, Rohit B.,Mane, Kishor D.,Rupanawar, Bapurao D.,Korekar, Pranjal,Sudalai,Suryavanshi, Gurunath
, p. 724 - 728 (2020/01/23)
A new heterogeneous catalytic system (Ti-superoxide/saccharin/TBHP) has been developed that efficiently catalyzes oxidative amidation of aldehydes to produce various primary amides. The protocol employs saccharin as amine source and was found to tolerate a wide range of substrates with different functional groups. Moderate to excellent yields, catalyst reusability and operational simplicity are the main highlights. A possible mechanism and the role of the catalyst in oxidative amidation have also been discussed.
Copper-Catalyzed Self-Condensation of Benzamide: Domino Reactions towards Quinazolinones
Sayyad, Nisar,Cele, Zamani,Aleti, Rajeshwar Reddy,Bera, Milan,Cherukupalli, Srinivasulu,Chandrasekaran, Balakumar,Kushwaha, Narva Deshwar,Karpoormath, Rajshekhar
supporting information, p. 5382 - 5388 (2018/10/20)
We herein report a simple and highly efficient microwave-assisted, copper-catalyzed and ligand-free synthetic method for 2-substituted 4(3H)-quinazolinones as domino reaction. This reaction proceeds via self-condensation of substrate (2-bromo/iodo benzamide) in the presence of a strong base and copper catalyst. The substituted quinazolinones were obtained in one-pot reaction by intramolecular cyclization (condensation) via Ullmann–type intermediate. Both the intermediates and quinazolinones were obtained in good yield and can be further used as building blocks for developing the potential novel drug-like compounds.
One-Pot Preparation of Aromatic Amides, 4-Arylthiazoles, and 4-Arylimidazoles from Arenes
Yamamoto, Takahiro,Togo, Hideo
, p. 4187 - 4196 (2018/08/21)
Simple treatment of arenes with α-bromoacetyl chloride and AlCl3, followed by the reaction with molecular iodine and aq. NH3, thioamides, or amidines gave the corresponding primary aromatic amides, 4-arylthiazoles, or 4-arylimidazoles in good yields, respectively. Aryl α-bromomethyl ketones are the key intermediates in those reactions. Primary aromatic amides were formed from arenes through the reaction of aryl α-bromomethyl ketones with molecular iodine and aq. NH3, and 4-arylthiazoles and 4-arylimidazoles were formed from arenes through the reactions of aryl α-bromomethyl ketones with thioamides and amidines, respectively, in one pot under transition-metal-free conditions.
Base-promoted nucleophilic fluoroarenes substitution of C–F bonds
Su, Ji,Chen, Qian,Lu, Le,Ma, Yuan,Auyoung, George Hong Lok,Hua, Ruimao
supporting information, p. 303 - 307 (2017/12/11)
With the use of KOH/DMSO as the superbase medium, the nucleophilic fluoroarene substitution for C–F bonds is presented. The transformation proceeds smoothly with the use of fluoroarenes bearing not only electron-withdrawing group, but also electron-donating group and a variety of nucleophiles such as alcohols, phenols, amines, amides and nitrogen-heterocyclic compounds. The double nucleophilic substitution using ortho-difluoroarenes and nucleophiles bearing ortho-dinucleophilic groups results in the formation of 2,3-dihydro-1,4-benzodioxins, dibenzo[b,e][1,4]dioxins and 10H-phenoxazines in moderate to good yields.
Preparation method of alkoxy benzamide
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Paragraph 0026; 0028; 0030; 0031, (2017/08/24)
The invention relates to a novel preparation method of alkoxy benzamide. Specifically, the method comprises steps as follows: chlorobenzonitrile is taken as a raw material and subjected to a reaction with alkaline substances in the presence of a catalyst, alkoxy benzoyl cyanide is generated and subjected to a hydrolysis reaction, and alkoxy benzamide is generated. The method has the advantages that the raw material is cheap and available, reaction conditions are mild, and postprocessing is convenient and simple.
A selective hydration of nitriles catalysed by a Pd(OAc)2-based system in water
Sanz Sharley, Daniel D.,Williams, Jonathan M.J.
supporting information, p. 4090 - 4093 (2017/09/27)
In situ formation of a [Pd(OAc)2bipy] (bipy = 2,2′-bipyridyl) complex in water selectively catalyses the hydration of a wide range of organonitriles at 70 °C. Catalyst loadings of 5 mol% afford primary amide products in excellent yields in the absence of hydration-promoting additives such as oximes and hydroxylamines.
Efficient Hydration of Nitriles Promoted by Gallic Acid Derived from Renewable Bioresources
Deng, Tao,Wang, Cheng-Zhang
, p. 1349 - 1353 (2017/04/14)
An efficient gallic acid promoted nitriles hydration at room temperature with ethanol/water as a solvent has been developed. The present protocol offers a wide range of amides in moderate to good yields. Moreover, galla chinensis extract can serve as the promoter to perform the hydration, which also shows the potential utilization of natural feedstocks.
Visible Light-Induced Iodine-Catalyzed Transformation of Terminal Alkynes to Primary Amides via C≡C Bond Cleavage under Aqueous Conditions
Dighe, Shashikant U.,Batra, Sanjay
supporting information, p. 500 - 505 (2016/02/12)
The visible light-induced iodine-catalyzed oxidative cleavage of the C≡C bond for transforming terminal alkynes into primary amides in the presence of ammonia under aqueous conditions is described. This metal-free protocol which ensued via initial hydroamination of the acetylene bond followed by liberation of diiodomethane (CH2I2) was found to be applicable to aromatic, heteroaromatic and aliphatic alkynes.
Hofmann Rearrangement of Carboxamides Mediated by N-Bromoacetamide
Jevti?, Ivana I.,Do?en-Mi?ovi?, Ljiljana,Ivanovi?, Evica R.,Ivanovi?, Milovan D.
, p. 1550 - 1560 (2016/06/01)
An efficient, one-pot procedure for the Hofmann rearrangement of aromatic and aliphatic amides has been developed. Methyl and benzyl carbamates are produced with N-bromoacetamide in the presence of lithium hydroxide or lithium methoxide, in high yields. β-Phenylamino amides gave five-membered cyclic ureas stereospecifically. Side products of aryl or benzyl bromination were minimized. This procedure offers an easy access to various protected amines or diamines, which represent important synthetic precursors.
