5395-00-6Relevant articles and documents
Hydrogen bonding and structure of 2-hydroxy-N-acylanilines in the solid state and in solution
Hibbert, Frank,Mills, Judith F.,Nyburg, Stanley C.,Parkins, Adrian W.
, p. 629 - 634 (1998)
In crystals of 2-hydroxy-N-benzoylaniline and 2-hydroxy-N-trifluoroacetylaniline, ribbons of molecules are held by intermolecular hydrogen bonds between the hydrpxy and carbonyl groups of adjacent molecules. The O ... H ... O bond lengths are 2.65 and 2.7
In Situ Formation of Cationic π-Allylpalladium Precatalysts in Alcoholic Solvents: Application to C-N Bond Formation
Steinsoultz, Philippe,Bailly, Aurélien,Wagner, Patrick,Oliva, Estefania,Schmitt, Martine,Grimaud, Laurence,Bihel, Frédéric
, p. 560 - 567 (2022/01/03)
We report an efficient Buchwald-Hartwig cross-coupling reaction in alcoholic solvent, in which a low catalyst loading showed excellent performance for coupling aryl halides (I, Br, and Cl) with a broad set of amines, amides, ureas, and carbamates under mild conditions. Mechanistically speaking, in a protic and polar medium, extremely bulky biarylphosphine ligands interact with the dimeric precatalyst [Pd(π-(R)-allyl)Cl]2 to form the corresponding cationic complexes [Pd(π-(R)-allyl)(L)]Cl in situ and spontaneously. The resulting precatalyst further evolves under basic conditions into the corresponding L-Pd(0) catalyst, which is commonly employed for cross-coupling reactions. This mechanistic study highlights the prominent role of alcoholic solvents for the formation of the active catalyst.
Iron-catalyzed oxidative amidation of acylhydrazines with amines
Wang, Yi-Jie,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping
supporting information, (2021/08/18)
A new approach for amide bond formation via a mild and efficient Iron-catalyzed cross-coupling reaction of acylhydrazines and amines using TBHP as oxidant is described. This protocol is compatible with a wide range of amines and acylhydrazines. In addition, the synthetic application of the reaction is presented.
Method for preparing amide compound by photocatalysis of organic amine
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Paragraph 0052-0053, (2021/06/06)
The invention relates to the technical field of organic synthesis, in particular to a method for preparing amide compounds through photocatalysis of organic amine. The preparation method comprises the following steps: mixing tetrahalomethane with a solvent, sequentially adding an amine compound, a catalyst and organic carboxylic acid, performing stirring and reacting under an oxygen-containing atmosphere and an illumination condition, and performing separating and purifying to obtain the amide compound with a structure shown in formulas V-VII. According to the method, the reaction is carried out in the air atmosphere under the illumination condition at room temperature and normal pressure, the reaction condition is mild, the raw material source is wide, the cost is low, the byproduct generated after the reaction is the halogen simple substance, the added value is high, a large amount of waste is avoided, and the method has higher atom economy and environmental friendliness and is beneficial to large-scale production.
An Environmentally Benign, Catalyst-Free N?C Bond Cleavage/Formation of Primary, Secondary, and Tertiary Unactivated Amides
Kumar, Vishal,Dhawan, Sanjeev,Girase, Pankaj Sanjay,Singh, Parvesh,Karpoormath, Rajshekhar
, p. 5627 - 5639 (2021/11/11)
Herein, we report an operationally simple, cheap, and catalyst-free method for the transamidation of a diverse range of unactivated amides furnishing the desired products in excellent yields. This protocol is environmentally friendly and operates under extremely mild conditions without using any promoter or additives. Significantly, this strategy has been implied in the chemoselective synthesis of a pharmaceutical molecule, paracetamol, on a gram-scale with excellent yield. We anticipate that this universally applicable strategy will be of great interest in drug discovery, biochemistry, and organic synthesis.
Chromium-catalyzed ligand-free amidation of esters with anilines
Chen, Changpeng,Ling, Liang,Luo, Meiming,Zeng, Xiaoming
supporting information, p. 762 - 766 (2021/04/14)
Amides are important structural motifs in pharmaceutical and agrochemical chemistry because of the intriguing biological active properties. We report here the amidation of commercially available esters with anilines that was promoted by low-cost and air-stable chromium(III) pre-catalyst combined with magnesium, providing access to amides. This reaction occurs without the use of external ligands in a simple operation. Mechanistic studies indicate that a reactive aminated Cr species responsible for the amidation can be considered, which may be formed by reaction of low-valent Cr with aniline followed by reduction with hydrogen evolution.
Compound containing bipyrazole ring, intermediate thereof and application thereof
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Paragraph 0287-0289, (2020/05/14)
The invention discloses a compound containing a bipyrazole ring, and an intermediate and application thereof. The invention provides the compound containing a bipyrazole ring, as shown in a formula Iwhich is described in the specification. The compound can be used as a ligand, is high in selectivity, and is suitable for the application range of amide in C-N coupling and the C-C coupling reactionof arylboronic acid and aryl chloride, especially coupling with aryl chloride.
Preparation method of compound containing bipyrazole ring and intermediate thereof
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Paragraph 0287-0289, (2020/05/14)
The invention discloses a preparation method of a compound containing a bipyrazole ring and an intermediate of the compound. The preparation method of a bipyrazole ring-containing compound as shown ina formula I comprises the following steps: (1) adding alkali into a mixture of a bipyrazole ring compound as shown in a formula I-1 and a solvent for replacement reaction to obtain a mixed system; and (2) adding an organic phosphorus compound shown as a formula I-2 into the mixed system in the step (1), and carrying out a phosphonation reaction shown in the specification, so as to obtain the bipyrazole ring-containing compound shown as the formula I, wherein R1 and R2 are independently a C1-C6 alkyl group, a C3-C8 cycloalkyl group and a phenyl group, R3 is a C1-C6 alkyl group, and X is halogen. The prepared compound containing a bipyrazole ring can be used as a ligand, and is suitable for the application range of amide in C-N coupling and the C-C coupling reaction of arylboronic acid andaryl chloride.
Para -Selective copper-catalyzed C(sp2)-H amidation/dimerization of anilides via a radical pathway
Viveki, Amol B.,Garad, Dnyaneshwar N.,Gonnade, Rajesh G.,Mhaske, Santosh B.
supporting information, p. 1565 - 1568 (2020/02/13)
Copper-catalyzed amidation/dimerization of anilides via regioselective C(sp2)-H functionalization is achieved. The para-selective amidation is accomplished on the anilide aromatic ring via a radical pathway leading to C-N bond formation in the presence of ammonium persulfate as a radical source/oxidant for the copper catalyst. The developed protocol tolerates a wide range of anilide substrates. The regioselectivity is confirmed by single-crystal X-ray studies.
Rhodium-Catalyzed Addition of Organozinc Iodides to Carbon-11 Isocyanates
Fouad, Moustafa H.,Ismailani, Uzair S.,Mair, Braeden A.,Munch, Maxime,Rotstein, Benjamin H.
, p. 2746 - 2750 (2020/04/16)
Amides were prepared using rhodium-catalyzed coupling of organozinc iodides and carbon-11 (11C, t1/2 = 20.4 min) isocyanates. Nonradioactive isocyanates and sp3 or sp2 organozinc iodides generated amides in yields of 13%-87%. Incorporation of cyclotron-produced [11C]CO2 into 11C-amide products proceeded in yields of 5%-99%. The synthetic utility of the methodology was demonstrated through the isolation of [11C]N-(4-fluorophenyl)-4-methoxybenzamide ([11C]6g) with a molar activity of 267 GBq μmol-1 and 12% radiochemical yield in 21 min from the beginning of synthesis.
