- CATALYST FOR CONVERTING ESTER TO AMIDE USING HYDROXYL GROUP AS ORIENTATION GROUP
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Provided is a method for amidating a hydroxy ester compound at a high chemical selectivity. The amidation reaction method for a hydroxy ester compound comprises, in the presence of a catalyst containing a compound of a transition metal of the group 4 or group 5 in the periodic table, reacting at least one kind of hydroxy ester compound selected from the group consisting of an α-hydroxy ester compound, a β-hydroxy ester compound, a γ-hydroxy ester compound and a δ-hydroxy ester compound with an amino compound so as to amidate an ester group having a hydroxyl group at the α-, β-, γ- or δ-position of the hydroxy ester compound.
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Paragraph 0059-0061
(2021/03/13)
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- Copper-catalyzed Goldberg-type C-N coupling in deep eutectic solvents (DESs) and water under aerobic conditions
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An efficient and selectiveN-functionalization of amides is first reportedviaa CuI-catalyzed Goldberg-type C-N coupling reaction between aryl iodides and primary/secondary amides run either in Deep Eutectic Solvents (DESs) or water as sustainable reaction media, under mild and bench-type reaction conditions (absence of protecting atmosphere). Higher activities were observed in an aqueous medium, though the employment of DESs expanded and improved the scope of the reaction to include also aliphatic amides. Additional valuable features of the reported protocol include: (i) the possibility to scale up the reaction without any erosion of the yield/reaction time; (ii) the recyclability of both the catalyst and the eutectic solvent up to 4 consecutive runs; and (iii) the feasibility of the proposed catalytic system for the synthesis of biologically active molecules.
- Cicco, Luciana,Hernández-Fernández, Jose A.,Salomone, Antonio,Vitale, Paola,Ramos-Martín, Marina,González-Sabín, Javier,Presa Soto, Alejandro,Perna, Filippo M.,Capriati, Vito,García-álvarez, Joaquín
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supporting information
p. 1773 - 1779
(2021/03/14)
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- Iodine and Br?nsted acid catalyzed C–C bond cleavage of 1,3-diketones for the acylation of amines
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A metal-free N-acylation method of anilines with 1,3-diketones has been developed, by using iodine and p-toluene sulfonic acid as the co-catalysts. The reaction can proceed in 1,4-dioxane at elevated temperature to produce the corresponding amides with 48–89% yields. Further, the gram-scale experiment was carried out under the standard conditions and the possible mechanism was proposed.
- Zhou, Xiao-Yu,Chen, Xia,Yang, Dan
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supporting information
p. 177 - 184
(2019/11/26)
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- Cu-Mediated Synthesis of Indolines and Dihydroisoquinolinones through Arylperfluoroalkylation of Unactivated Alkenes
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The copper-mediated fluroalkylation/cyclization of N-allyl anilines has been described using fluoroalkyl iodides as fluoroalkylation reagents for the first time. The reaction provides an efficient and direct access to 3-fluoroalkyl indolines in moderate to good yields with unactivated double bonds as the radical acceptor. This protocol combines a simple experimental procedure with low-costing fluoroalkylated sources and excellent functional group tolerance.
- Li, Dandan,Wang, Yan,Jia, Zhenzhen,Ou, Zhaocheng,Dong, Yongrui,Lv, Cunjie,Fu, Guangbin,Liang, Deqiang
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p. 4797 - 4804
(2019/08/12)
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- SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
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A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.
- Zhang, Guofu,Zhao, Yiyong,Xuan, Lidi,Ding, Chengrong
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supporting information
p. 4911 - 4915
(2019/07/31)
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- Air-stable Bis(pentamethylcyclopentadienyl) Zirconium Perfluorooctanesulfonate as an Efficient and Recyclable Catalyst for the Synthesis of N-substituted Amides
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Bis(pentamethylcyclopentadienyl) zirconium perfluorooctanesulfonate is an air-stable and water-tolerant Lewis acid. This complex exhibited good thermal stability and high solubility in polar organic solvents. The compound showed relatively strong acidity, with an acid strength of 0.8Ho≤3.3, and high catalytic efficiency for the synthesis of N-substituted amides via the reaction of carboxylic acids with amines, the Ritter reaction of nitriles with alcohols, and the amination of alcohols with amides. Moreover, the complex had good reusability. This catalytic system affords a simple and efficient way to synthesize N-substituted amides.
- Li, Ningbo,Wang, Lingxiao,Zhang, Liting,Zhao, Wenjie,Qiao, Jie,Xu, Xinhua,Liang, Zhiwu
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p. 3532 - 3538
(2018/08/01)
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- Preparation method of N-aryl amide compounds
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The invention belongs to the technical field of synthesis of compounds, and in particular relates to a preparation method of N-aryl amide compounds. The method comprises the following steps: dissolving amide, a copper catalyst and alkali in an organic solvent, and adding a halogenated aromatic hydrocarbon; then, irradiating with ultraviolet light for carrying out a reaction for 12-24h under nitrogen protection; after the reaction is completed, concentrating reaction liquid by using a rotary evaporator; separately and purifying by means of column chromatography silica gel to obtain the N-aryl amide. The method provided by the invention replaces heating with illumination, does not need to add a ligand, is simple in process, mild in conditions and lower in economic cost, and has higher functional group compatibility and universality.
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Paragraph 0032-0034
(2018/12/13)
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- Ni-Catalyzed cross-coupling of aryl thioethers with alkyl Grignard reagents via C-S bond cleavage
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A Ni-catalyzed cross-coupling of aryl thioethers with alkyl Grignard reagents, accompanied by the cleavage of the C(aryl)-SMe bond, has been presented. This method is distinguished by its mild conditions and moderate functional group tolerance, such as hydroxyl, halogen, and heterocycles, which should provide a straightforward access to the modification of sulfur-containing molecules.
- Zhu, Dan,Shi, Lei
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supporting information
p. 9313 - 9316
(2018/08/29)
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- Selective Oxidative Coupling Reaction of Isocyanides Using Peroxide as Switchable Alkylating and Alkoxylating Reagent
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A switchable oxidative coupling reaction of isocyanide and peroxide has been disclosed. In the presence of iron catalyst, the coupling reaction affords N-arylacetamides in good yields. By simply replacing the iron with copper catalyst, another different coupling reaction takes place in which peroxide can serve as alkoxylating source. This protocol represents a new fundamental coupling of two basic chemicals involving C?C and C?O bond-forming process. The unusual reactivity of an isocyano group in a radical reaction acting formally as an amidoyl synthon has also been well established. The experiment outcome reveals that aromatic isocyanides are particularly compatible reaction partners in present coupling reaction, whereas no desired products are observed when aliphatic isocyanides are used. (Figure presented.).
- Zhang, Xinglu,Liu, Zhiqiang,Gao, Yu,Li, Feng,Tian, Yaming,Li, Chunju,Jia, Xueshun,Li, Jian
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supporting information
p. 272 - 277
(2017/11/13)
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- Organocatalytic Asymmetric Annulation between Hydroxymaleimides and Nitrosoarenes: Stereoselective Preparation of Chiral Quaternary N-Hydroxyindolines
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An unusual and highly effective asymmetric annulation of nitrosoarenes with hydroxymaleimides catalyzed by a chiral bifunctional amine squaramide catalyst has been disclosed. A wide range of highly fused chiral N-hydroxyindolines with two consecutive quaternary stereocenters and multifunctional groups were directly and effectively prepared in excellent yields (up to >99%) with complete regioselective cyclization and excellent stereoselectivities (up to >99:1 dr and >99% ee). The efficiency and potentials of the new reaction and the target chiral entities were well demonstrated by delicate transformations into a series of new chiral indolines.
- Yang, Yu,Ren, Hong-Xia,Chen, Feng,Zhang, Zheng-Bing,Zou, Ying,Chen, Chao,Song, Xiang-Jia,Tian, Fang,Peng, Lin,Wang, Li-Xin
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supporting information
p. 2805 - 2808
(2017/06/07)
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- Carbon Tetrabromide/Triphenylphosphine-Activated Beckmann Rearrangement of Ketoximes for Synthesis of Amides
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An efficient Beckmann rearrangement of ketoximes was developed using carbon tetrabromide/triphenylphosphine as an organocatalyst without addition of any acids or metals. The reaction showed good functional group tolerance and gave various amides in moderate to good yields.
- Gao, Peng,Bai, Zijing
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supporting information
p. 1673 - 1677
(2017/10/05)
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- AIBN-promoted amidation of anilines with 1, 3-diketones via oxidative cleavage of C–C bond under aerobic conditions
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N-Acylation of anilines with 1, 3-diketones promoted by AIBN (2-2′-azoisobutyronitrile) under metal-free and peroxide-free conditions in the presence of molecular oxygen as oxidant has been described. This protocol proceeds by the oxidative cleavage of C–C bond with simultaneous intermolecular C–N bond formation under mild conditions.
- Rao, Sadu Nageswara,Mohan, Darapaneni Chandra,Adimurthy, Subbarayappa
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p. 4889 - 4894
(2016/07/18)
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- An Iron-Catalyzed Direct Approach to Amides from Benzyl Azides via C-C Bond Cleavage
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A novel iron-catalyzed transformation of benzyl azides to give the corresponding amides via C-C bond cleavage under mild reaction conditions is developed. This method provides a new synthetic tool for the construction of amides and the opportunity to accomplish C-C functionalization under mild conditions.
- Ou, Yang,Qin, Chong,Song, Song,Jiao, Ning
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p. 2971 - 2975
(2015/09/28)
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- Carboxyl activation of 2-mercapto-4,6-dimethylpyrimidine through n-acyl-4,6-dimethylpyrimidine-2-thione: A chemical and spectrophotometric investigation
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2-Mercapto-4,6-dimethylpyrimidine, as effective carboxyl activating group, has been successfully proved by converting it into respective acyl derivatives and the subsequent conversion to the amides and esters respectively using amines, amino alcohols and alcohols. The aminolysis and esterification were monitored chemically and spectrophotometrically. This paved way to establish that the above mercaptopyrimidine derivative is an efficient carboxyl activating group applicable in solid phase peptide synthesis.
- Rajan
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p. 287 - 291
(2015/01/30)
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- An eco-benign and highly efficient procedure for N-acylation catalyzed by heteropolyanion-based ionic liquids using carboxylic acid under solvent-free conditions
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An eco-benign and highly efficient route for N-acylation of amines has been developed by treating amines with corresponding carboxylic acids in the presence of 2 mol % of heteropolyanion-based ionic liquids as catalysts under solvent-free conditions. This practical reaction could tolerate a wide range of substrates. Thus, various N-acylation products including N-acyl α-amino acid derivatives were obtained in moderate to excellent yields at 70 C to 120 C. Moreover, recycling studies revealed that heteropolyanion-based ionic liquids were easily reusable for this N-acylation. This method provides a green and much improved protocol over the existing methods.
- Chen, Zhikai,Fu, Renzhong,Chai, Wen,Zheng, Hao,Sun, Lin,Lu, Qiang,Yuan, Rongxin
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p. 2237 - 2245
(2014/03/21)
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- Reductive acylation of nitroarenes to anilides by sodium sulfite in carboxylic acids
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A facile and efficient reductive acylation of aromatic nitro compounds to corresponding anilides using a sodium sulfite-carboxylic acid system for the first time has been reported. The sodium sulfite reagent provides the colorless reductant in combination with stoichiometric amounts of carboxylic acid and enables the formation of anilides from nitroarenes without any additives in good to excellent yields with high purities and simple work-up. Furthermore, this protocol provides a novel and complementary access to some industrially important chemicals in kilogram scale under mild conditions.
- Ghaffarzadeh, Mohammad,Akhavan, Pegah
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supporting information
p. 1417 - 1419
(2016/09/28)
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- Ligand-enabled triple C-H activation reactions: One-pot synthesis of diverse 4-aryl-2-quinolinones from propionamides
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Diverse 4-aryl-2-quinolinones are prepared from propionamides in one pot by ligand-promoted triple sequential C-H activation reactions and a stereospecific Heck reaction. In these cascade reactions, three new C-C bonds and one C-N bond are formed to rapidly build molecular complexity from propionic acid. Building complexity: Diverse 4-aryl-2-quinolinones such as 1 are prepared from propionamides in one pot by pyridine ligand-promoted triple sequential C-H activation reactions and a stereospecific Heck reaction. In these cascade reactions, three new C-C bonds and one C-N bond are formed to rapidly build molecular complexity from propionic acid.
- Deng, Youqian,Gong, Wei,He, Jian,Yu, Jin-Quan
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supporting information
p. 6692 - 6695
(2014/07/08)
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- Isolation of magnetic material from fly ash and its catalytic performance for N-acetylation under solvent free conditions
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Coal fly ash is a waste material generated in huge amount due to'burning of coal for the generation of electricity. Magnetic material isolated from fly ash was characterized by XRD, FT-IR, SEM-EDS, XPS, BET and TEM techniques. It is used as heterogeneous catalyst for the JV-acetylation reactions of amines with carboxylic acids. The present methodology is environmentally benign, cost effective and offers several advantages, like excellent yields, short reaction times, reusability of catalyst and simple work up procedure. The case studies cover new approaches and experiments, which will articulate the requirement for industrial application of sustainable chemistry.
- Dhokte, Aashish O.,Shaikh, Uzmaparveen K.,Lande, Machhindra K.,Arbad, Babasaheb R.
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p. 837 - 844
(2013/08/23)
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- H2O2-mediated oxidative formation of amides from aromatic amines and 1,3-diketones as acylation agents via C-C bond cleavage at room temperature in water under metal-free conditions
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1,3-Diketones, as novel acylation agents, reacted with aromatic amines promoted by commercially available H2O2 (30% aq.) as the sole oxidant at room temperature under metal-free conditions in water, leading to a novel and rapid amide bond formation strategy. The reported method is high-yielding, simple and mild, and is the first example of the use of 1,3-diketones as acylation agents via C-C bond cleavage.
- Sun, Xi,Wang, Min,Li, Pinhua,Zhang, Xiuli,Wang, Lei
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supporting information
p. 3289 - 3294
(2013/12/04)
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- Malonic ester amide synthesis: An efficient methodology for synthesis of amides
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A general methodology malonic ester amide synthesis has been demonstrated, which uses α-substituted/unsubstituted diethyl malonates for the decarboxylative acylation of various aromatic/heteroaromatic primary/secondary amines to form one-carbon homologated amides, thus providing easy access to amides with odd/even chain lengths and an array of substituents on the alkyl/aryl part while avoiding use of acyl chlorides or peptide coupling reagents. Copyright
- Mahajan, Pankaj S.,Mahajan, Jyoti P.,Mhaske, Santosh B.
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p. 2508 - 2516
(2013/07/25)
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- ZnO nanofluid as a structure base catalyst for chemoselective amidation of aliphatic carboxylic acids
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ZnO nanofluids were synthesized and utilized as a new reaction media in the preparation of amides via direct amidation of aliphatic carboxylic acids with primary amines under solvent-free conditions. High yields and good selectivity are achieved with this psudo-homogeneous catalyst, while the recovered nanoZnO was reusable.
- Tamaddon, Fatemeh,Aboee, Fatemeh,Nasiri, Alireza
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experimental part
p. 194 - 197
(2012/02/04)
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- New, efficient, selective, and one-pot method for acylation of amines
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Hydrazine hydrate with acetic and propionic acids was an efficient reagent for acylation of primary and secondary amines at reflux temperatures. The reported one-pot method is high-yielding, simple, mild, and inexpensive. Copyright Taylor & Francis Group, LLC.
- Basanagouda, Mahantesha,Kulkarni, Manohar V.,Kalkhambkar, Raj G.,Kulkarni, Geeta M.
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p. 2929 - 2940
(2008/12/22)
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- Mercury-catalyzed rearrangement of ketoximes into amides and lactams in acetonitrile
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(Chemical Equation Presented) An acetonitrile solution of mercury(II) chloride has been found to catalyze efficiently the conversion of a diverse range of ketoximes into their corresponding amides/lactams.
- Ramalingan, Chennan,Park, Yong-Tae
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p. 4536 - 4538
(2008/02/04)
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- Facile preparation of amides from azo compounds by SmI2
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Azo compounds are conveniently reduced by SmI2/THF system and successively acylated smoothly with aromatic and aliphatic acyl chlorides or acid anhydrides to afford corresponding amides in one pot under mild and neutral conditions.
- Li, Xue,Zhang, Yongmin
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p. 1576 - 1578
(2007/10/03)
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- One pot preparation of amides from azo compounds by Sm/TiCl4
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Azo compounds were conveniently reduced by a system consisting of Sm/TiCl4 to produce aniline anions. This anion species reacted smoothly with aliphatic acyl chlorides or acid anhydrides to afford corresponding amides under mild and neutral conditions.
- Li, Xue,Zhang, Yong-Min
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p. 1219 - 1222
(2007/10/03)
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- Infrared spectra of N-aryl substituted amides 2/4-XC6H 4NHCOR (R = H, CH3-iXi, C6H 5 or C6H5Cl; X = H, Cl or CH3 and i = 0, 1, 2 or 3)
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Several N-(aryl)-substituted amides of the general formula, 2/4-XC 6H4NHCOR (where X = H, Cl or CH3 and R = H, CH3, CH2CH3, CH(CH3)2, C(CH3)3, C6H5 or C6H 5Cl) are prepared, characterised and their infrared spectra measured in the solid state and analysed. Generally chloro substitution in the side chain increases the C=O absorptions, while that of methyl groups lower the wave numbers. Amides with trimethyl substituted side chains absorb at higher wavenumbers. But the N-H and C-N stretching vibrations do not show particular trends on side chain substitution. This may be due to the fact that the spectra were recorded in the solid state and the compounds may crystallise in different forms in the solid state. The intercorrelations of C=O and N-H absorption frequencies of all the amides have been made. The correlations are reasonably linear with some exceptions for the reasons stated above.
- Gowda, B. Thimme,Jyothi,Jayalakshmi,Damodara
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p. 564 - 568
(2007/10/03)
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- One-pot reductive conversion of nitroarenes to N-arylacetamides mediated by metallic samarium
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Nitroarenes can be reduced and then converted to N-arylacetamides by metallic samarium in the presence of acetic anhydride, acetic acid and methanol in excellent yields by a one pot-procedure.
- Zhang, Yandong,Zhang, Yongmin
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p. 596 - 598
(2007/10/03)
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- METHOD OF PROCESSING OF HYDROGEN FOR REDUCTIVE ACYLATION OF NITRO, AZIDO AND CYANO ARENES
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The present invention relates to a method for processing of hydrogen for the reductive acylation of nitro, azido and cyano arenes. More particularly, this invention relates to an improved process for the preparation of amides and anilides using C3-C7 carboxylic acids as proton source/acylating agents employing Fe3+-montmorillonite as a catalyst.
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- Method of processing of hydrogen for reductive acylation of nitro, azido and cyano arenes
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A method for processing of hydrogen for the reductive acylation of nitro, azido and cyano arenes is disclosed. More particularly, improved process for the preparation of amides and anilides using C3-C7carboxylic acids as proton source/acylating agents employing Fe3+-montmorillonite as a catalyst is disclosed.
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Page column 5
(2008/06/13)
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- Solid phase synthesis of amides by the Beckmann rearrangement of ketoxime carbonates
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In the presence of trifluoroacetic acid, ketoxime benzyl carbonates undergo a Beckmann rearrangement to the corresponding amides. This reaction was translated to a solid support by immobilizing oximes in the form of mixed carbonates derived from hydroxymethylpolystyrene in order to produce a diversity of amides with high efficiency.
- His, Sarah,Meyer, Christophe,Cossy, Janine,Emeric, Gibert,Greiner, Alfred
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p. 8581 - 8584
(2007/10/03)
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- Thermal behaviors of ionic liquids under microwave irradiation and their application on microwave-assisted catalytic Beckmann rearrangement of ketoximes
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Microwave-assisted Beckmann rearrangements of ketoximes in room temperature ionic liquids have been accomplished successfully using only 5 mol% of H2SO4 as a catalyst.
- Lee, Jae Kyun,Kim, Dok-Chan,Song, Choong Eui,Lee, Sang-Gi
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p. 2301 - 2307
(2007/10/03)
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- Rhodium-catalyzed Beckmann rearrangement
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equation presented Beckmann rearrangement of oxime is catalyzed by [RhCl(cod)]2, trifluoromethanesulfonic acid, and tris(p-tolyl)phosphine in refluxing dichloroethane, giving the corresponding amide in good yield. Product/acid ratios of 10:20 can be attained in the reaction of benzophenone oximes.
- Arisawa, Mieko,Yamaguchi, Masahiko
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p. 311 - 312
(2007/10/03)
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- Aminolysis of N-Acylpyrazoles
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1-Acylpyrazoles reacted with amines having a tiny substituted to afford the corresponding amides.The aminolysis with bulky amines was controlled to be retarded by the steric factors.Due to this steric interaction, the stereoselective aminolysis was observed.This selectivity of aminolysis should increase the utility of pyrazoles as auxiliary compounds in the synthetic loop.
- Kashima, Choji,Fukuchi, Iwao,Takahashi, Katsumi,Hosomi, Akira
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p. 1407 - 1412
(2007/10/02)
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