- Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides
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A novel heterogeneous copper catalyst has been developed by supporting copper nanoparticles on activated charcoal via in situ reducing copper(II) with aqueous hydrazine as reductant. The characterization of Cu/C catalyst showed that the Cu0 nano-particles were formed on the surface of charcoal. This catalyst displayed good catalytic activities toward the N-arylation of primary amides and lactams with aryl iodides.
- Zhao, Rong,Dong, Wenwen,Teng, Jiangge,Wang, Zhiwei,Wang, Yunzhong,Yang, Jianguo,Jia, Qiang,Chu, Changhu
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supporting information
(2020/12/21)
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- Graphene oxide-catalyzed CSp3–H activation of methylarenes in aqueous medium: A unified metal-free access to amides and benzimidazoles
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Graphene oxide (GO)-catalyzed selective synthesis of amides via CSp3–H activation of methylarenes and consequent C–N bond formation with anilines under aqueous medium has been described. Oxygen functionality allied with GO surface played a dual role both as acid catalyst and oxidizing agent to some extent. However, GO has a copious effect on the reaction, shown by a high TOF value with TBHP as co-oxidant. The decisive role of carboxylic acid functional groups on GO nanosheets in this metal-free strategy has been confirmed and was monitored by various analytic techniques viz. Fourier transform-infrared, UV–Vis, Raman and XPS. A plausible mechanism was proposed by control experiments and by the isolation of the intermediate. Over-oxidation of methylarenes was not detected, and high recyclability of the carbocatalyst with its heterogeneous behavior facilitated the isolation and purification of the desired products. We have further explored the utility of this process for the chemoselective synthesis of benzimidazoles.
- Dandia, Anshu,Mahawar, Dinesh Kumar,Sharma, Ruchi,Badgoti, Ranveer Singh,Rathore, Kuldeep S.,Parewa, Vijay
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- Method for synthesizing amide compound through photocatalysis in water phase
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The invention discloses a method for synthesizing an amide compound through photocatalysis in a water phase. The method comprises the following steps: putting catalysis amounts of a free radical initiator, an amine derivative, a carboxylic acid derivative, a phase transfer catalyst, an inorganic base and water into a reaction container, carrying out a reaction in a photocatalysis reaction instrument at certain power under a room temperature condition, after a certain time, carrying out extraction by using a small amount of ethyl acetate, and carrying out recrystallization, so as to obtain theamide compound, wherein the free radical initiator is eosin, methyl orange, sodium persulfate, ammonium persulfate or potassium peroxodisulfate, the phase transfer catalyst is tetrabutylammonium bromide, and the power of the photocatalytic reaction instrument is 5W. By adopting the method disclosed by the invention, toxic thionyl chloride or phosphorus oxychloride is not needed for a chlorinationreaction, water is adopted as a solvent, a novel photocatalysis method is used, and the amide compound with a high yield can be prepared through a room-temperature reaction for 2-5 hours with an incandescent light bulb of 5W, and in addition, the method is simple in aftertreatment, and low in cost and is an ideal green synthesis method of amide compounds.
- -
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Paragraph 0018-0048
(2019/10/01)
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- Electrochemical: N-acylation synthesis of amides under aqueous conditions
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An electrochemical N-acylation of carboxylic acids with amines was reported. The sustainable TBAB electrocatalysis proceeded with excellent chemoselectivity and positional selectivity, and with ample scope, allowing electrochemical N-acylation under mild reaction conditions at room temperature in water. Moreover, the synthetic utility of the current method is demonstrated by the synthesis of melatonin.
- Ke, Fang,Xu, Yiwen,Zhu, Suning,Lin, Xiaoyan,Lin, Chen,Zhou, Sunying,Su, Huimin
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supporting information
p. 4329 - 4333
(2019/08/21)
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- The visualization of hERG channels in living cells: Via a fluorescent probe regulated by the synergy between solvatochromism and molecular rotation based on simple targeting of the group 4-benzylaniline
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A highly sensitive fluorescent probe CBH based on solvatochromism and molecular rotation was designed and developed for imaging of hERG channels by employing a novel targeting group 4-benzylaniline. More importantly, CBH has the potential for the quantita
- Qiao, Zhen,Zhou, Qiqi,Zhang, Hongyi,Wei, Ningning,Zhang, Yanru,Wang, Kewei
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supporting information
p. 5515 - 5518
(2019/05/16)
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- Synthetic method of anesthetic analgesic drug
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The invention discloses a synthetic method of an anesthetic analgesic drug. According to the synthetic method, 4-piperidinecarboxylic acid is used as a raw material and subjected to alkylation, bromination, methylation, acylation and the like to prepare the anesthetic analgesic drug. The method avoids the usage of highly toxic cyanide, so the safety and controllability of operation are improved; the method avoids an elimination reaction in reaction process, thereby accelerating reaction speed and shortening reaction time; and the method reduces reaction temperature, shortens the reaction time,and is more suitable for industrial production.
- -
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Paragraph 0115; 0120; 0121
(2019/12/29)
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- Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
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The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
- Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
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p. 6404 - 6407
(2017/12/08)
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- Amine Activation: Synthesis of N-(Hetero)arylamides from Isothioureas and Carboxylic Acids
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A novel method for N-(hetero)arylamide synthesis based on rarely explored amine activation, rather than classical acid activation, is reported. The activated amines are easily prepared using a three-component reaction with commercial reagents. The new method shows a broad scope including challenging amides not (efficiently) accessible via classical protocols.
- Zhu, Yan-Ping,Sergeyev, Sergey,Franck, Philippe,Orru, Romano V. A.,Maes, Bert U. W.
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supporting information
p. 4602 - 4605
(2016/09/28)
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- DEHYDRATION CONDENSATION AGENT
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PROBLEM TO BE SOLVED: To provide a novel compound useful as a dehydration condensation agent. SOLUTION: This invention relates to a compound represented by formula (I) [where each symbol is as defined in the specifications] and to a method for producing a carboxylic acid derivative (ester, amide or the like) that uses the compound as a dehydration condensation agent. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT
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Paragraph 0355; 0359; 0365
(2018/09/08)
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- Phosphine-free atmospheric carbonylation of aryl iodides with aniline derivatives in the presence of a reusable silica-supported palladium catalyst
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Various palladium catalysts were obtained by the immobilisation of palladium on silica, modified with imidazolium salts. The efficiency of the catalysts was greatly dependent on the choice of the anion of the imidazolium salt, the palladium precursor and on the conditions of heterogenisation. Palladium acetate immobilised on silica with grafted imidazolium chloride moieties was shown to be a selective and recyclable catalyst for atmospheric aminocarbonylation of aryl iodides with aromatic amines in DMF. It was proved that the greater loss of palladium in DMSO can be explained by the formation of soluble palladium complexes.
- Urbán, Béla,Papp, Máté,Srankó, Dávid,Skoda-F?ldes, Rita
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p. 150 - 157
(2015/02/19)
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- HUMAN PLASMA KALLIKREIN INHIBITORS
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Disclosed are compounds of formula (I), as described herein, and pharmaceutically acceptable salts thereof. The compounds are inhibitors of plasma kallikrein. Also provided are pharmaceutical compositions comprising at least one compound of the invention, and methods involving use of the compounds and compositions of the invention in the treatment and prevention of diseases and conditions characterized by unwanted plasma kallikrein activity.
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Page/Page column 168; 169
(2015/11/02)
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- Ligand-free CuTC-catalyzed N-arylation of amides, anilines and 4-aminoantipyrine: Synthesis of N-arylacrylamides, 4-amido-N-phenylbenzamides and 4-amino(N-phenyl)antipyrenes
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N-Arylation of amides and anilines with aryl iodides was efficiently catalyzed by copper thiophenecarboxylate under ligand-free conditions with good to excellent yields. A variety of substituted aryl iodides, amides, anilines and 4-aminoantipyrine were found to be applicable to the simple catalytic system. Furthermore, some practical, unique secondary amides, such as N-arylacrylamides and 4-amido-N-phenylbenzamides, and 4-amino(N-phenyl)antipyrenes, which are difficult to obtain by the classical methods, were prepared.
- Quan, Zheng-Jun,Xia, Hai-Dong,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
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- Copper-catalyzed regioselective synthesis of N-aryl amides from aldoximes and aryl halides
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Ligand-assisted copper-catalyzed reaction of aldoximes with aryl halides is described for the regioselective synthesis of N-aryl amides. This protocol is simple and compatible with a wide range of functional groups attached to the aryl ring of the halides as well as aldoximes. Copyright
- Panda, Niranjan,Mothkuri, Raghavender,Nayak, Dinesh Kumar
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supporting information
p. 1602 - 1605
(2014/03/21)
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- Copper-Catalyzed Regioselective Synthesis of N-Aryl Amides from Aldoximes and Aryl Halides
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Ligand-assisted copper-catalyzed reaction of aldoximes with aryl halides is described for the regioselective synthesis of N-aryl amides. This protocol is simple and compatible with a wide range of functional groups attached to the aryl ring of the halides as well as aldoximes.
- Panda, Niranjan,Mothkuri, Raghavender,Nayak, Dinesh Kumar
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supporting information
p. 1602 - 1605
(2015/10/05)
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- COMPOUNDS FOR THE TREATMENT AND PREVENTION OF INFECTIONS
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Provided herein are compounds of Formula (I) or (II): (I) (II) harmaceutically acceptable salts, tautomers, prodrugs, and stereoisomers thereof, and pharmaceutical compositions thereof, wherein X, RN, R1,R3,R4,
- -
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Paragraph 00283
(2014/02/15)
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- An efficient copper-catalyzed N-arylation of amides: Synthesis of N-arylacrylamides and 4-amido-N-phenylbenzamides
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Copper-catalyzed intermolecular C-N bond-forming reactions between aryl iodides and amides are described using sodium ascorbate, which is both cheap and nontoxic, as the additive. A variety of functionalized amides including some practical, unique secondary amides, such as N-arylacrylamides and 4-amido-N-phenylbenzamides, which are difficult to obtain by the classical methods, are prepared. Furthermore, some tertiary amides are prepared by using copper thiophenecarboxylate.
- Quan, Zheng-Jun,Xia, Hai-Dong,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
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p. 8368 - 8374
(2013/09/02)
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- Recyclable, highly efficient and low cost nano-MgO for amide synthesis under SFRC: A convenient and greener 'NOSE' approach
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A clean synthesis of amide derivatives has successfully been accomplished utilizing reusable nano-MgO under 'SFRC' (solvent free reaction condition). The 'green-ness' of this protocol makes it a benign alternative for the large scale synthesis.
- Das, Vijay Kumar,Devi, Rashmi Rekha,Thakur, Ashim Jyoti
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p. 118 - 125
(2013/06/26)
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- Aminocarbonylations employing Mo(CO)6 and a bridged two-vial system: Allowing the use of nitro group substituted aryl iodides and aryl bromides
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A bridged two-vial system aminocarbonylation protocol where Mo(CO) 6 functions as an external in situ solid source of CO has been developed. For the first time both nitro group containing aryl/heteroaryl iodides and bromides gave good to excellent yields in the Mo(CO) 6-mediated and palladium(0)-catalyzed conversion to benzamides, while the identical one-vessel protocol afforded extensive reduction of the nitro functionality. The above-mentioned bridged two-compartment protocol furnished good results with both primary amines and secondary amines and sluggish aniline nucleophiles at 65-85 C reaction temperatures.
- Nordeman, Patrik,Odell, Luke R.,Larhed, Mats
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p. 11393 - 11398
(2013/02/23)
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- Efficient copper-catalyzed N-arylation of amides and imidazoles with aryl iodides
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The C-N cross-coupling of amides and imidazoles with aryl iodides is described using CuI in tetrabutylammonium bromide (TBAB) under ligand-free conditions. The reaction is simple, general, and efficient affording the C-N cross-coupled products in shorter time and in high yield. Georg Thieme Verlag Stuttgart ? New York.
- Ali, Md. Ashif,Saha, Prasenjit,Punniyamurthy, Tharmalingam
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supporting information; experimental part
p. 908 - 910
(2010/04/29)
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- Efficient and facile method for the nitration of aromatic compounds by nitric acid in micellar media
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Aromatic compounds were efficiently nitrated under mild reaction conditions by employing HNO3 in the presence of anionic (sodium dodecyl sulfate, SDS), cationic (cetyl trimethyl ammonium bromide, CTAB), and nonionic (Triton-X 100) micelles. The reaction rapidly afforded corresponding mononitro derivatives in fair to good yields with high regioselectivity. This new method offers an environmentally safe reaction condition to minimize the waste products.
- Sana,Tasneem,Ali, M. Moazzam,Rajanna,Saiprakash
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experimental part
p. 2949 - 2953
(2009/12/03)
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- Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone complex as a reagent for preparation of carboxylic acid bromides
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Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone complex was successfully used as a new reagent for the synthesis of carboxylic acid bromides which were isolated as individual substances or were identified by conversion into the corresponding anilides. The reaction is chemoselective, and it can be applied to polyfunctional compounds, e.g., hydroxy acids.
- Matveeva,Podrugina,Sandakova,Zefirov
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p. 1469 - 1472
(2007/10/03)
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- Use of glycogen phosphorylase inhibitors
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The invention provides methods of treating prophylactically an individual in whom Type 2 diabetes mellitus has not yet presented, but in whom there is an increased risk of developing such condition, which methods comprise administering to an individual in need thereof an effective amount of a glycogen phosphorylase inhibitor; effective amounts of a glycogen phosphorylase inhibitor and a non-glycogen phosphorylase inhibiting anti-diabetic agent; or effective amounts of a glycogen phosphorylase inhibitor and an anti-obesity agent. The invention further provides methods of treating prophylactically an individual in whom Type 2 diabetes mellitus has not yet presented, but in whom there is an increased risk of developing such condition, which methods comprise administering to an individual in need thereof a pharmaceutical composition comprising effective amounts of a glycogen phosphorylase inhibitor and a non-glycogen phosphorylase inhibiting anti-diabetic agent; or effective amounts of a glycogen phosphorylase inhibitor and an anti-obesity agent.
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- Solid phase synthesis of amides using Mukaiyama's reagent
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A new solid-phase synthetic method using Mukaiyama's reagent under mild conditions is reported to prepare amides in high purity without purification after cleavage from the resins.
- Tao, Bin,Boykin, David W.
-
-
- Inhibitors of human glycogen phosphorylase
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The present invention is directed to a novel binding site for a glycogen phosphorylase inhibitor found within a glycogen phosphorylase enzyme. The novel binding site allows the design novel of glycogen phosphorylase inhibitors.
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- Glycogen phosphorylase inhibitors
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This invention relates to certain 5-acyl-2-oxo-indole-3-carboxamides useful as inhibitors of glycogen phosphorylase, methods of treating glycogen phosphorylase dependent diseases or conditions with such compounds and pharmaceutical compositions comprising such compounds. This invention also relates to pharmaceutical compositions comprising those 5-acyl-2-oxo-indole-3-carboxamides in combination with antidiabetes agents and methods of treating glycogen phosphorylase dependent diseases or conditions with such compositions.
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- Substituted cyclic amine compound, production process thereof and pharmaceutical composition for circulatory organ use containing the same
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A substituted cyclic amine compound represented by the following general formula (1) STR1 wherein each of R1 to R5 represents a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group or the like, A represents a carbonyl group or a sulfonyl group, B represents a methine moiety or a nitrogen atom, D represents a methine moiety, a nitrogen atom or =N(→O)-- and n is an integer of 2 to 3; and synthetic methods thereof. The inventive compound is useful in preventing and treating circulatory organ-related diseases such as hypertension, ischemic heart disease, cerebrovascular disease, peripheral circulatory disease and the like.
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- NUCLEOPHILIC ADDITION OF N-LITHIOAMIDES TO ?-ARENECHROMIUM TRICARBONYL COMPLEXES. PREPARATION OF ANILINE DERIVATIVES
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A simple procedure for the preparation of aniline derivatives by the nucleophilic addition of nitrogen anions to ?-(arene)chromium tricarbonyl complexes is described.
- Keller, L.,Times-Marshall, K.,Behar, S.,Richards, K.
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p. 3373 - 3376
(2007/10/02)
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- REACTIONS OF IMIDIC ACID DERIVATIVES WITH NUCLEOPHILIC REAGENTS. ALKALINE HYDROLYSIS OF N-PHENYLBENZIMIDOYL-4-DIMETHYLAMINOPYRIDINIUM SALTS IN A WATER-DIOXANE MIXTURE
-
First order in each of the reagents is characteristic of the alkaline hydrolysis of N-phenylbenzimidoylpyridinium salts +C5H4N(CH3)2>=NC6H5>.Cl- (R=3-CH3, H, 3-OCH3, 3-Br, 3-NO2> in aqueous dioxane (1:1) at 25 deg C with constant ionic strenght μ 0.2 (sodium chloride).On the basis of the proximity of the Hammett ρ parameters a common mechanism, involving the formation of an intermediate addition product in the rate-controlling stage, is proposed for the bimolecular reaction of these compounds (ρR 1.7) and 4-nitrophenyl N-phenylbenzimidates RC6H4C(OC6H4NO2)=NC6H5 (ρR 2.0) with the hydroxide ion.The salt effect of sodium perchlorate, sodium bromide, and sodium chloride in the process, due to the participation of ion pairs in the reaction, are discussed.
- Prudchenko, A. P.,Drizhd, L. P.,Savelova, V. A.
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p. 742 - 746
(2007/10/02)
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- EFFECT OF THE STRUCTURE ON THE RATE OF THE REACTIONS OF AROYL CHLORIDES WITH PRIMARY ARYLAMINES IN MIXTURES OF tert-BUTYL ALCOHOL AND CHLOROBENZENES. THE TRANSITION THROUGH ISOPARAMETRIC POINTS WITH RESPECT TO THE STRUCTURE PARAMETERS
-
The rate of the reactions of aroyl chlorides with primary arylamines in 3.5, 5, and 7M solutions of tert-butyl alcohol in chlorobenzene at 25 deg C was measured.The effect of the structure of the reagents on the process rate was determined quantitatively by means of the Hammett-Taft and crossed correlation equations.The isoparametric points with respect to the structure of the substrate and the nucleophile were reached experimentally, and the transition through some of these points was also realised.It was found that the specific solvation of the primary arylamines by the tert-butyl alcohol was nonuniform in that an incre ase in the concentration of the alcohol in the investigated range reduced, did not change, and increased the rates of the reactions with 3-chloroaniline, 3-nitroaniline, and 3-nitro-5-methoxycarbonylaniline respectively.The effect of specific solvation on the behavior of the correlation parameters is discussed.
- Shpan'ko, I. V.,Likhomanenko, E. E.
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p. 1702 - 1710
(2007/10/02)
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- REACTIONS OF IMIDIC ACID DERIVATIVES WITH NUCLEOPHILIC REAGENTS. KINETICS AND QUANTITATIVE RELATIONSHIPS OF THE ALKALINE HYDROLYSIS OF THE 4-NITROPHENYL ESTERS OF DIARYLIMIDIC ACIDS
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In the kinetics of the alkaline hydrolysis of the 4-nitrophenyl esters of arylimidic acids R1C6H4C(OC6H4NO2-4)=NC6H4R2 in a water-dioxane mixture (1:1 by volume) with a constant ionic strength first order is observed in each of the reagents.The reaction rate depends little on the nature of the electrolyte (NaCl, NaClO4, LiClO4) and decreases with increase in the concentration of the salt in the solution.The ρ constants for the bimolecular process ρR1 = 2.0 0.1 and ρR2 = 2.4 0.2 agree with an addition-elimination mechanism with the formation of a tetrahedral intermediate product in the rate-determining stage.
- Prudchenko, A. P.,Drizhd, L. P.,Savelova, V. A.
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p. 923 - 926
(2007/10/02)
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- Synthesis and Antiviral Activity of Sulfonamidobenzophenone Oximes and Sulfonamidobenzamides
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To find antiviral agents, various sulfonamidobenzophenone oximes (II) were synthesized from the appropriate m-sulfonamidobenzophenones by hydroxylamine reaction.The reaction products were generally obtained as syn/anti mixtures which were separable by fractional crystallization.The anti isomer had more potent antipoliovirus activity than the syn isomer.Various sulfonamidobenzamides (III) which were structurally related to II were synthesized by the reaction of amino-substituted benzamides with sulfuryl chloride or amines with (aminosulfonyl)benzoyl chloride.Antiviral activity was examined by the plaque-inhibition test.Compounds 5, 36, and 69 exhibited strong antipicornavirus activity.The structure-activity relationships are discussed.
- Ogata, Masaru,Matsumoto, Hiroshi,Shimizu, Sumio,Kida, Shiro,Wada, Toru,et al.
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p. 417 - 423
(2007/10/02)
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- MUTUAL EFFECT OF THE STRUCTURES OF THE REAGENTS ON THE RATE OF THE REACTIONS OF AROYL CHLORIDES WITH PRIMARY ARYLAMINES IN DIOXANE AND MIXTURES OF CHLOROBENZENE WITH tert-BUTYL ALCOHOL
-
The rate of the reactions of aroyl chlorides with primary arylamines in specifically solvating media (dioxane, 0.1 M and 2 M solutions of tert-butyl alcohol in chlorobenzene) was measured.The joint effect of the structures of the reagents on the rate of the process in the employed media assessed quantitatively by crossed correlation.It was shown that the mutual effect of the structural factors on the reactivity is nonadditive in a 0.1 M solution of tert-butyl alcohol in chlorobenzene and additive in dioxane and also in a 2 M solution of tert-butyl alcohol in chlorobenzene.The effect of the structure of the reagents and specific solvation on the nature of the transition states of the reactions is discussed.
- Likhomanenko, E. E.,Shpan'ko, I. V.,Litvinenko, L. M.,Goncharov, A. N.
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p. 2341 - 2347
(2007/10/02)
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- JOINT EFFECT OF THE STRUCTURE OF THE REAGENTS AND THE POLARITY OF THE MEDIUM ON THE RATE OF REACTIONS OF AROYL CHLORIDES WITH PRIMARY ARYLAMINES. CROSSED CORRELATION
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The kinetics of the reactions of aroyl chlorides with primary arylamines in volume mixtures of chlorobenzene with nitrobenzene were studied with crossed variation in the structures of the reagents.The effect of various factors (the structure of the primary arylamines, the structure of the aroyl chlorides, the polarity of the medium), varied separately and in pairs, and also the joint effect of the three factors on the process rate were assessed.It was found that the structure of the reagents and the polarity of the medium have a nonadditive type of mutual effect on the reactivity of the aroyl chloride-primary arylamine system.The influence of the varied factors on the nature of the transition states in the reactions is discussed.
- Shpan'ko, I. V.,Likhomanenko, E. E.,Litvinenko, L. M.,Goncharov, A. N.
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p. 1390 - 1397
(2007/10/02)
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