- CC-Verknuepfung von Styrol mit Isocyanaten an Nickel(0), eine Katalytische Synthese von Zimtsaeureamiden
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Isocynates react with styrene at ligand-nickel(0) systems by 1/1 C-C coupling giving azanickelcyclopentanones.The nickela five-membered rings obtained in this way are characterized spectroscopically, and their reaction modes are described.Depending on the ligands and special reaction conditions it is shown that with continuous, slow addition of the isocyanate to the solution of styrene and the Lig-Ni0 starting complex catalytic formation of cinnamanilide occurs.
- Hernandez, Elisa,Hoberg, Heinz
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Read Online
- Umpolung cyclization reaction of: N -cinnamoylthioureas in the presence of DBU
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A novel regioselective cyclization reaction of N-cinnamoylthioureas leading to six- or five-membered heterocyclic compounds was developed. N-Cinnamoylthioureas in the presence of trifluoroacetic acid (TFA) underwent the well-established intramolecular cycloaddition reaction to give 2-imino-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones in good yields. On the other hand, the reaction with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) proceeded in an unprecedented umpolung cyclization fashion to afford five-membered 2-imino-1,3-thiazolidin-4-ones and/or 2-thioxoimidazolidine-4-ones. The reaction was considered to occur via a cycloadduct of DBU with the cinnamoyl moiety followed by intramolecular attack of the thiourea group.
- Saito, Rei,Uemura, Naohiro,Ishikawa, Hiroki,Magara, Akina,Yoshida, Yasushi,Mino, Takashi,Kasashima, Yoshio,Sakamoto, Masami
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Read Online
- Manganese Catalyzed Direct Amidation of Esters with Amines
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The transition metal catalyzed amide bond forming reaction of esters with amines has been developed as an advanced approach for overcoming the shortcomings of traditional methods. The broad scope of substrates in transition metal catalyzed amidations remains a challenge. Here, a manganese(I)-catalyzed method for the direct synthesis of amides from a various number of esters and amines is reported with unprecedented substrate scope using a low catalyst loading. A wide range of aromatic, aliphatic, and heterocyclic esters, even in fatty acid esters, reacted with a diverse range of primary aryl amines, primary alkyl amines, and secondary alkyl amines to form amides. It is noteworthy that this approach provides the first example of the transition metal catalyzed amide bond forming reaction from fatty acid esters and amines. The acid-base mechanism for the manganese(I)-catalyzed direct amidation of esters with amines was elucidated by DFT calculations.
- Fu, Zhengqiang,Wang, Xinghua,Tao, Sheng,Bu, Qingqing,Wei, Donghui,Liu, Ning
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p. 2339 - 2358
(2021/02/03)
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- Chlorination Reaction of Aromatic Compounds and Unsaturated Carbon-Carbon Bonds with Chlorine on Demand
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Chlorination with chlorine is straightforward, highly reactive, and versatile, but it has significant limitations. In this Letter, we introduce a protocol that could combine the efficiency of electrochemical transformation and the high reactivity of chlorine. By utilizing Cl3CCN as the chloride source, donating up to all three chloride atom, the reaction could generate and consume the chlorine in situ on demand to achieve the chlorination of aromatic compounds and electrodeficient alkenes.
- Liu, Feng,Wu, Na,Cheng, Xu
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supporting information
p. 3015 - 3020
(2021/05/05)
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- Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
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Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
- Bai, Jin,Li, Shangzhang,Li, Wanfang,Qu, Erdong,Zheng, Yan
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supporting information
(2021/12/27)
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- Iron-catalyzed oxidative amidation of acylhydrazines with amines
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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.
- Wang, Yi-Jie,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping
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supporting information
(2021/08/18)
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- Tungsten-Catalyzed Transamidation of Tertiary Alkyl Amides
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Transamidation has recently emerged as a straightforward and convenient means to diversify amides. However, the kinetically and thermodynamically demanding transamidation of notoriously robust, fully alkyl-substituted tertiary amides still remains a longstanding challenge. Here, we describe a method for the activation of tertiary alkyl amides to streamline transamidation using simple tungsten(VI) chloride as a catalyst and chlorotrimethylsilane as an additive. The highly electrophilic and oxophilic tungsten catalyst enables the selective scission of a C-N bond of tertiary alkyl amides to effect transamidation of a myriad of structurally and electronically diverse tertiary alkyl amides and amines. Mechanistic study implies that the synergistic effect of the catalyst and the additive could pronouncedly induce the nucleophilic acyl substitution of tertiary alkyl amide with amine to realize transamidation.
- Feng, Fang-Fang,Liu, Xuan-Yu,Cheung, Chi Wai,Ma, Jun-An
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p. 7070 - 7079
(2021/06/30)
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- Chromium-catalyzed ligand-free amidation of esters with anilines
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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.
- Chen, Changpeng,Ling, Liang,Luo, Meiming,Zeng, Xiaoming
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supporting information
p. 762 - 766
(2021/04/14)
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- Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant
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An unprecedented N-demethylation of N-methyl amides has been developed by use of N-fluorobenzenesulfonimide as an oxidant with the aid of a copper catalyst. The conversion of amides to carbinolamines involves successive single-electron transfer, hydrogen-atom transfer, and hydrolysis, and is accompanied by formation of N-(phenylsulfonyl)benzenesulfonamide. Carbinolamines spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.
- Yi, Xuewen,Yi, Xuewen,Lei, Siyu,Liu, Wangsheng,Che, Fengrui,Yu, Chunzheng,Liu, Xuesong,Wang, Zonghua,Zhou, Xin,Zhang, Yuexia
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supporting information
p. 4583 - 4587
(2020/05/05)
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- Synthesis of Linear α,β-Unsaturated Amides from Isocyanates and Alkenylaluminum Reagents
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A new approach has been developed for the synthesis of linear α,β-unsaturated amides by the direct coupling of isocyanates with alkenylaluminum reagents. At room temperature, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional-group tolerance in the absence of any catalyst or additive.
- Chen, Bo,Wu, Xiao-Feng
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supporting information
p. 788 - 792
(2020/05/19)
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- Palladium-catalyzed carbonylative synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent
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In this work, an interesting procedure for the synthesis of α,β-unsaturated amides from aryl azides and alkenylaluminum reagent has been developed. With palladium as the catalyst and XPhos as the ligand under carbon monoxide pressure, the desired α,β-unsaturated amides were isolated in good to excellent yields with good functional group tolerance. Remarkably, this procedure also represents an example on addition of organometallic reagent to isocyanates for α,β-unsaturated amides synthesis.
- Chen, Bo,Wu, Xiao-Feng
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p. 160 - 163
(2020/02/11)
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- Design of enamides as new selective monoamine oxidase-B inhibitors
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Objectives: To develop of new class of selective and reversible MAO-B inhibitors from enamides. Methods: Syntheses of the titled derivatives (AD1–AD11) were achieved by reacting cinnamoyl chloride and various primary and secondary amines in basic medium. All eleven compounds were investigated for in vitro inhibitory activities against recombinant human MAO-A and MAO-B. The reversibilities of lead compound inhibitions were analysed by dialysis. MTT assays of lead compounds were performed using normal VERO cell lines. Key findings: Compounds AD3 and AD9 exhibited the greatest inhibitory activity against MAO-B with IC50 values of 0.11 and 0.10?μm, respectively, and were followed by AD2 and AD1 (0.51 and 0.71?μm, respectively). Most of the compounds weakly inhibited MAO-A, with the exceptions AD9 and AD7, which had IC50 values of 4.21 and 5.95?μm, respectively. AD3 had the highest selectivity index (SI) value for MAO-B (>363.6) and was followed by AD9 (SI 42.1). AD3 and AD9 were found to be competitive inhibitors of MAO-B with Ki values of 0.044?±?0.0036 and 0.039?±?0.0047?μm, respectively. Reversibility experiments showed AD3 and AD9 were reversible inhibitors of MAO-B; dialysis restored the activity of MAO-B to the reference level. MTT assays revealed AD3 and AD9 were non-toxic to normal VERO cell lines with IC50 values of 153.96 and 194.04?μg/ml, respectively. Computational studies provided hypothetical binding modes for AD3 and AD9 in the binding cavities of MAO-A and MAO-B. Conclusions: These results encourage further studies on the enamide scaffold as potential drug candidates for the treatment of Alzheimer's and Parkinson's diseases.
- Kavully, Fathima Sahla,Oh, Jong Min,Dev, Sanal,Kaipakasseri, Swafvan,Palakkathondi, Ashique,Vengamthodi, Ajeesh,Abdul Azeez, Rinshana Fathima,Tondo, Anna Rita,Nicolotti, Orazio,Kim, Hoon,Bijo
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p. 916 - 926
(2020/04/15)
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- Investigation of anti-inflammatory potential of N-arylcinnamamide derivatives
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A series of sixteen ring-substituted N-arylcinnamanilides, previously described as highly antimicrobially effective against a wide spectrum of bacteria and fungi, together with two new derivatives from this group were prepared and characterized. Moreover, the molecular structure of (2E)-N-(2-bromo-5-fluorophenyl)-3-phenylprop-2-enamide as a model compound was determined using single-crystal X-ray analysis. All the compounds were tested for their anti-inflammatory potential, and most tested compounds significantly attenuated the lipopolysaccharide-induced NF-κB activation and were more potent than the parental cinnamic acid. (2E)-N-[2-Chloro-5-(trifluoromethyl)phenyl]-3-phenylprop-2-enamide, (2E)-N-(2,6-dibromophenyl)-3-phenylprop-2-enamide, and (2E)-N-(2,5-dichlorophenyl)-3-phenylprop-2-enamide demonstrated the highest inhibition effect on transcription factor NF-κB at the concentration of 2 μM and showed a similar effectiveness as the reference drug prednisone. Several compounds also decreased the level of TNF-α. Nevertheless, subsequent tests showed that the investigated compounds affect neither IκBα level nor MAPKs activity, which suggests that the N-arylcinnamanilides may have a different mode of action to prednisone. The modification of the C(2,5)0 or C(2,6)0 positions of the anilide core by rather lipophilic and bulky moieties seems to be preferable for the anti-inflammatory potential of these compounds.
- Ho?ek, Jan,Kos, Ji?í,Strhársky, Tomá?,?erná, Lucie,?tarha, Pavel,Van?o, Ján,Trávní?ek, Zdeněk,Devínsky, Ferdinand,Jampílek, Josef
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- Copper-Catalyzed Electrophilic Amidation of Organotrifluoroborates with Use of N-Methoxyamides
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A copper-catalyzed electrophilic amidation of aryltrifluoroborates with use of N-methoxyamides is reported. The reaction shows high functional group compatibility derived from two distinct features: 1) the high stability of the N-methoxyamides and 2) the nonbasic mild conditions in the presence of LiCl. The developed method can also be applied to the synthesis of enamides, which are widely distributed in natural products. Preliminary mechanistic studies suggest that the initial step is the transmetalation of the aryltrifluoroborate by the assistance of LiCl, and the resulting aryl copper intermediate provides the anilide through non-SN2 oxidative addition to the N-methoxyamide and subsequent reductive elimination.
- Banjo, Shona,Nakasuji, Eiko,Meguro, Tatsuhiko,Sato, Takaaki,Chida, Noritaka
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supporting information
p. 7941 - 7947
(2019/05/24)
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- Direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions
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The direct synthesis of N-arylamides via the coupling of aryl diazonium tetrafluoroborates and nitriles under transition-metal-free conditions has been developed. The reported protocol is practical and represents an efficient method to produce functionalized amides in moderate to good yields.
- Xiong, Biquan,Wang, Gang,Xiong, Tao,Wan, Liming,Zhou, Congshan,Liu, Yu,Zhang, Panliang,Yang, Changan,Tang, Kewen
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supporting information
p. 3139 - 3142
(2018/07/13)
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- Palladium-Catalyzed Carbonylative Synthesis of α,β-Unsaturated Amides from Styrenes and Nitroarenes
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A procedure on palladium-catalyzed selective aminocarbonylation of styrenes with nitroarenes for the synthesis of α,β-unsaturated amides has been developed. A range of substituted α,β-unsaturated amides were synthesized in moderate to good yields. Interestingly, nitroarenes act as both a nitrogen source and oxidant, and Mo(CO)6 acts as a solid CO source and reductant in this catalytic system.
- Peng, Jin-Bao,Geng, Hui-Qing,Li, Da,Qi, Xinxin,Ying, Jun,Wu, Xiao-Feng
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supporting information
p. 4988 - 4993
(2018/08/24)
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- A to aryl diazonium tetrafluoroborate salts with a nitrile preparation machine acid radical amine compounds (by machine translation)
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The invention provides a high-efficiency, high-selective synthesis of different substituted functional group containing organic amide compound, it adopts the cuprous iodide as a catalyst, in order to aryl diazonium tetrafluoroborate salts compounds and organic nitrile compound as the reaction substrate, the reaction system by adding the organic solvent, water and alkali. The advantage of this method: cheap and easily obtained catalyst; the substrate has a high applicability; mild reaction conditions, safe and reliable; the resulting target product selectivity is close to 100%, yield is as high as 90% or more. The method solves the traditional synthetic organic amide compound of rigorous reaction conditions, the reaction selectivity is poor, the experimental procedure is complicated, the productivity is low and needs to be used for the environment of a harmful reagent and the like, it has good industrial application prospect. The invention also provides a corresponding different substituted functional group containing organic amide compound. (by machine translation)
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Paragraph 0031
(2018/06/04)
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- Heterocoumarins Are Selective Carbonic Anhydrase IX and XII Inhibitors with Cytotoxic Effects against Cancer Cells Lines
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We have synthesized a new series of coumarin-based compounds demonstrating high selectivity and potent effects with low nanomolar affinity against the tumor associated carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA IX and XII. A number of these compounds were evaluated ex vivo against human prostate (PC3) and breast (MDA-MB-231) cancer cell lines. Compounds 4b and 15 revealed effective cytotoxic effects after 48 h of incubation in both normoxic and hypoxic conditions with PC3 cancer cell line. However, compound 3 showed selective cytotoxic effects against MDA-MB-231 in hypoxic condition. These results may be of particular importance for the choice of future drug candidates targeting hypoxic tumors and metastases, considering the fact that a selective carbonic anhydrase CA IX inhibitor (SLC-0111) is presently in phase II clinical trials.
- Angeli, Andrea,Trallori, Elena,Carta, Fabrizio,Di Cesare Mannelli, Lorenzo,Ghelardini, Carla,Supuran, Claudiu T.
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supporting information
p. 947 - 951
(2018/09/12)
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- Hypervalent Iodine(III)-Promoted Phenyl Transfer Reaction from Phenyl Hydrazides to Nitriles
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A useful transformation of nitriles to N-phenyl amides has been achieved through a novel intermolecular phenyl transfer reaction from phenyl hydrazides and N-addition to nitriles in the presence of PIFA under mild and solvent-free conditions. This cross-coupling reaction includes the oxidative cleavage of sp2 C-N bonds of phenyl hydrazides to form a phenyl radical and the subsequent N-addition to cyanos to form new sp2 C-N bonds and provides efficient access to various N-phenyl amides in moderate to good yields under mild reaction conditions.
- Yan, Yan,Zhang, Zhiguo,Wan, Yameng,Zhang, Guisheng,Ma, Nana,Liu, Qingfeng
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supporting information
p. 7957 - 7963
(2017/08/14)
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- Cationic N-Heterocyclic Carbene Copper-Catalyzed [1,3]-Alkoxy Rearrangement of N-Alkoxyanilines
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The [1,3]-alkoxy rearrangement reactions of N-alkoxyanilines were efficiently catalyzed by cationic N-heterocyclic carbene (NHC)-Cu catalysts in affording 2-alkoxyaniline derivatives in good to excellent yields with high functional group compatibility. For N-alkoxyanilines having an electron-withdrawing substituent at the meta-position, the alkoxy group selectively migrated to the more hindered ortho-position. In contrast, the alkoxy group migrated to the less hindered ortho-position for N-alkoxyanilines having an electron-donating substituent. Mechanistic studies suggest that the rearrangement reactions proceed via an intramolecular route.
- Nakamura, Itaru,Jo, Takeru,Ishida, Yasuhiro,Tashiro, Hiroki,Terada, Masahiro
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supporting information
p. 3059 - 3062
(2017/06/23)
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- Metal-Free Synthesis of 3-Arylquinolin-2-ones from Acrylic Amides via a Highly Regioselective 1,2-Aryl Migration: An Experimental and Computational Study
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Combined experimental and theoretical investigations into the phenyliodine bis(trifluoroacetate) (PIFA)-mediated reaction of N-arylcinnamamide to produce 3-arylquinolin-2-one derivatives have been conducted. High regioselectivity during the aryl migration process was observed in 3,3-disubstituted acrylamides. Density functional theory calculation was conducted in an attempt to understand the mechanism and the origin of the regioselectivity. On the basis of both the experimental and the theoretical results, a mechanism involving an oxidative annulation, followed by an aryl migration, has been proposed. The annulation is the regioselectivity determining step.
- Liu, Le,Zhang, Tonghuan,Yang, Yun-Fang,Zhang-Negrerie, Daisy,Zhang, Xinhao,Du, Yunfei,Wu, Yun-Dong,Zhao, Kang
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p. 4058 - 4065
(2016/06/08)
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- Green synthesis of isoxazoline derivatives using microwave irradiation and their antifungal activity
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Microwave irradiation method was used for synthesis of isoxazolines. Claisen Schmidt reaction of different aromatic aldehydes with acetanilide gave acrylamides (1a-1h) which on further reaction with hydroxylamine hydrochloride (in the presence of sodium hydroxide) afforded isoxazolines (2a-2h). Physical data of all the synthesized compounds were recorded. Isoxazolines were characterized by their IR and 1H NMR spectra. All the synthesized isoxazolines were screened for their antifungal activity against fungi namely Drechslera maydis and Rhizoctonia solani isolated from maize. Isoxazolines having chloro substitution on benzene ring found to be most effective followed by fluoro and nitro substituted compounds. None of the compound was registered as effective as Bavistin.
- Goyal, Akhil,Sharma, Sunita,Gaba, Jyoti,Kaur, Harleen
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p. 2169 - 2172
(2016/07/19)
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- Methylaluminoxane (MAO)-assisted direct amidation of esters
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Aliphatic and aromatic esters are efficiently transformed into amides in good to excellent yields, under mild conditions using methylaluminoxane (MAO). This reaction can be performed either at room temperature or by applying microwave irradiation.
- Desrat, Sandy,Ducousso, Aline,Gapil, Shelly,Remeur, Camille,Roussi, Fanny
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p. 385 - 387
(2015/02/19)
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- Direct amidation of carboxylic acids with amines under microwave irradiation using silica gel as a solid support
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A highly improved and green methodology for the direct amidation of carboxylic acids with amines using silica gel as a solid support and catalyst is described. The scope of this method is exemplified by the use of several aliphatic, aromatic, unsaturated and fatty acids. The reaction is also applied to different primary and secondary amines. Typically, the amines should be aliphatic, but aromatic amines can be used as well, though with lower yields. Several experiments to illustrate the selectivity of this methodology were also carried out with several more functionalized acids and amines. This approach is a substantial improvement over other previously described methods in amide synthesis.
- Ojeda-Porras, Andrea,Hernández-Santana, Alejandra,Gamba-Sánchez, Diego
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supporting information
p. 3157 - 3163
(2015/05/27)
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- Copper catalysed C-N bond formation via a sequential acylation and deacylation process: A novel strategy for the synthesis of benzanilides
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An efficient and mild oxidative amidation of aldehydes by means of acetanilides as amine components has been developed for the first time using copper catalysis. The approach is versatile and proceeds through sequential acylation and deacylation steps to afford benzanilides.
- Kumar, Saurabh,Vanjari, Rajeshwer,Guntreddi, Tirumaleswararao,Singh, Krishna Nand
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p. 9920 - 9924
(2015/02/19)
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- Copper-catalyzed oxidative amidation between aldehydes and arylamines under mild conditions
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A facile strategy to prepare amide bonds has been developed. A series of amide compounds, including heterocyclic amide compounds, were obtained with moderate to good yields ranging from 31-88% by using copper iodide (CuI) to catalyze the oxidative amidation between aldehydes and amines under solvent-free conditions at room temperature in air.
- Ding, Yongzheng,Zhang, Xian,Zhang, Dongyang,Chen, Yuting,Wu, Zhibing,Wang, Peiyi,Xue, Wei,Song, Baoan,Yang, Song
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supporting information
p. 831 - 833
(2015/02/19)
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- Tandem superelectrophilic hydroarylation of CC bond and carbonyl reduction in cinnamides: Synthetic rout to 3,3-diarylpropylamines, valuable pharmaceuticals
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Cinnamides ArCHCHCONRR′ in reactions with arenes Ar′H under the action of Bronsted (TfOH, FSO3H) or Lewis (AlBr3) superacids at rt for 1-2 h give CC bond hydroarylation products ArAr′CHCH2CONRR′ in yields of 63-98%. Reduction (LiAlH4/Et2O) of carbonyl group in the latter results in the formation of 3,3-diarylpropylamines ArAr′CHCH2CH2NRR′, valuable drugs. The reaction intermediates, superelectrophilic dications ArC+H-CH2C(OH+)NRR′, have been characterized by DFT calculations in terms of global electrophilicity index, natural charges, and atomic orbitals contributions.
- Zakusilo, Dmitry N.,Ryabukhin, Dmitry S.,Boyarskaya, Irina A.,Yuzikhin, Oleg S.,Vasilyev, Aleksander V.
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p. 102 - 108
(2015/02/02)
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- SYNTHESIS OF FUNCTIONALIZED AND UNFUNCTIONALIZED OLEFINS VIA CROSS AND RING-CLOSING METATHESIS
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The invention is directed to the cross-metathesis and ring-closing metathesis reactions between geminal disubstituted olefins and terminal olefins, wherein the reaction employs a Ruthenium or Osmium metal carbene complex. Specifically, the invention relates to the synthesis of alpha-functionalized or unfunctionalized olefins via intermolecular cross-metathesis and intramolecular ring-closing metathesis using a ruthenium alkylidene complex. The catalysts preferably used in the invention are of the general formulawherein:M is ruthenium or osmium;X and Xare each independently an anionic ligand;L is a neutral electron donor ligand; and,R, RR, R, R, and Rare each independently hydrogen or a substituent selected from the group consisting of C1-C20 alkyl, C2-C20 alkenyl, C2-C20 alkynyl, aryl, C1-C20 carboxylate, C1-C20 alkoxy, C2-C20 alkenyloxy, C2-C20 alkynyloxy, aryloxy, C2-C20 alkoxycarbonyl, C1-C20 alkylthio, C1-C20 alkylsulfonyl and C1-C20 alkylsulfinyl.
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Paragraph 0018; 0024
(2015/11/09)
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- Synthesis of Cinnamanilide Derivatives and Their Antioxidant and Antimicrobial Activity
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The amide derivatives of cinnamic acid were synthesized and their antimicrobial and antioxidant activities were investigated. The investigation of antimicrobial potentials of the compounds demonstrated a strong activity against 21 bacterial strains comprising Gram-positive and Gram-negative bacteria. Compounds 2a, 2b, and 3b showed strong antimicrobial activity against all microorganisms with the pMIC value ranging from 2.45 to 3.68. Compounds 2a, 3a, and 3b demonstrated strong antioxidant activity with % inhibition of the DPPH radical of 51% (±1.14), 41% (±1.01), and 50% (±1.23), respectively. These findings indicate that the amide derivatives of the cinnamic acid possess strong antibacterial and antioxidant activities.
- Nimse, Satish Balasaheb,Pal, Dilipkumar,Mazumder, Avijit,Mazumder, Rupa
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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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- TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide
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A new method with high efficiency for the synthesis of α,β- unsaturated amides from the easily prepared propargyl alcohols and TMSN 3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.
- Song, Xian-Rong,Song, Bo,Qiu, Yi-Feng,Han, Ya-Ping,Qiu, Zi-Hang,Hao, Xin-Hua,Liu, Xue-Yuan,Liang, Yong-Min
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p. 7616 - 7625
(2014/09/16)
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- Synthesis, photochemistry, DNA cleavage/binding and cytotoxic properties of fluorescent quinoxaline and quinoline hydroperoxides
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Novel fluorescent quinoxaline and quinoline hydroperoxides were shown to perform dual role as both fluorophores for cell imaging and photoinduced DNA cleaving agents. Photophysical studies of newly synthesized quinoxaline and quinoline hydroperoxides showed that they all exhibited moderate to good fluorescence. Photolysis of quinoxaline and quinoline hydroperoxides in acetonitrile using UV light above 350 nm resulted in the formation of corresponding ester compounds via γ-hydrogen abstraction by excited carbonyl chromophore. Single strand DNA cleavage was achieved on irradiation of newly synthesized hydroperoxides by UV light (≥350 nm). Both hydroxyl radicals and singlet oxygen were identified as reactive oxygen species (ROS) responsible for the DNA cleavage. Further, we showed quinoline hydroperoxide binds to ct-DNA via intercalative mode. In vitro biological studies revealed that quinoline hydroperoxide has good biocompatibility, cellular uptake property and cell imaging ability. Finally, we showed that quinoline hydroperoxide can permeate into cells efficiently and may cause cytotoxicity upon irradiation by UV light.
- Chowdhury, Nilanjana,Gangopadhyay, Moumita,Karthik,Pradeep Singh,Baidya, Mithu,Ghosh
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p. 188 - 198
(2014/01/06)
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- A novel one-step synthesis of benzo[b]furo[3,2-b]pyridines having an amino group at the 4-position from benzo[b]furo[3,2-d][1,3]oxazine
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A novel one-step synthesis of benzo[b]furo[3,2-b]pyridines having an amino group at the 4-position from benzo[b]furo[3,2-d][1,3]oxazine by treatment of various amines is described.
- Tabuchi, Yukako,Kakumoto, Yusa,Uchimoto, Hitomi,Kawasaki, Ikuo,Ohishi, Yoshitaka,Nishide, Kiyoharu
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p. 177 - 191
(2013/03/13)
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- Synthesis and structure-activity relationship analysis of caffeic acid amides as selective matrix metalloproteinase inhibitors
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Four series of acid amides were synthesized, and through measurement using a fluorogenic substrate assay with human recombinant MMP-1, MMP-2 and MMP-9, compound 3f showed considerable inhibitory activities against MMP-2, MMP-9 and the best selectivity over MMP-1. Preliminary structure-activity relationship analysis indicated that caffeic acid amides with electron-donating groups at para-position of amino phenyl group showed better inhibitory activities and selectivity than those with electron-withdrawing groups, and the presence of adjacent dihydroxy in the caffeoyl group was very important for the MMP-2 and MMP-9 inhibitory activities.
- Shi, Zhi-Hao,Li, Nian-Guang,Shi, Qian-Ping,Tang, Hao,Tang, Yu-Ping,Li, Wei,Yin, Lian,Yang, Jian-Ping,Duan, Jin-Ao
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p. 1206 - 1211
(2013/03/14)
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- Sulfated tungstate: A highly efficient catalyst for transamidation of carboxamides with amines
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An environmentally benign protocol for the transamidation of carboxamides with amines using sulfated tungstate, as a heterogeneous catalyst, has been developed. The method has been successfully applied to the synthesis of a wide range of aromatic and aliphatic amides and phthalimides. Efficient transformation, mild reaction conditions, easy product isolation and the potential reusability of the catalyst are attractive features.
- Pathare, Sagar P.,Jain, Ashish Kumar H.,Akamanchi, Krishnacharya G.
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p. 7697 - 7703
(2013/06/27)
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- Synthesis and anticancer activity of aminodihydroquinoline analogs: Identification of novel proapoptotic agents
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A series of 2-aminodihydroquinoline analogs were synthesized and their in vitro cytotoxicities against metastatic breast adenocarcinoma cell line MDA-MB-231 were tested. Five out of 16 compounds exhibited promising activity and structure-activity relationship revealed major role of dialkylaminoethyl substituents on dihydroquinoline ring for the activity. Two compounds, 5f and 5h, presented cytotoxicity with IC50 values of about 2 μM when the compounds were treated to the cells without serum. The cell proliferation was inhibited mildly when the cells cultured with serum. Flow cytometry analyses showed that those compounds arrested the cells at G2/M checkpoint when the cell cycle is active while they induce apoptosis when the cell growth is restricted due to the absence of growth factors. These results suggest the two novel compounds may have anticancer activity through cell cycle arrest and pro apoptosis mechanism.
- Lee, Eun,Han, Seulaa,Jin, Guo Hua,Lee, Hwa Jin,Kim, Woo-Young,Ryu, Jae-Ha,Jeon, Raok
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supporting information
p. 3976 - 3978
(2013/07/25)
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- Efficient amide formation from arylamines and esters promoted by AlCl 3/Et3N: An experimental and computational investigation
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Efficient and selective preparation of amides from arylamines and esters has been achieved with an AlCl3/Et3N pair under mild conditions. A large number of arylamines were successfully acylated to the corresponding amides in high yields and short reaction times. For instance, a 94% yield of p-bromoacetanilide was obtained from p-bromoaniline and ethyl acetate in 10 min at room temperature. In addition, a computational study on the N-acylation of amines was performed using density functional theory. It was found that the energy barrier for N-acylation of aniline is 10 kcal/mol higher than that of methylamine. In the presence of AlCl3, the activation energy for the N-acylation of aniline was reduced by 27.7 kcal/mol with the endothermic process becoming exothermic. Springer Science+Business Media B.V. 2012.
- Tong, Xinli,Ren, Zhangshun,Que, Xiaolong,Yang, Qiwu,Zhang, Wenqin
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p. 1961 - 1968
(2013/02/22)
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- Tert-butoxide-assisted amidation of esters under green conditions
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Efficient and green amidation reactions are of great importance. In this work, we demonstrate the tert-butoxide-assisted amidation of esters with amines under ambient conditions. Aliphatic and/or aromatic esters were converted into the corresponding amides under mild conditions in good to excellent yields. It is noteworthy that the reaction is highly efficient, rapid, versatile, green and economical, and will find great practical application in organic synthesis, biochemistry, and industrial chemistry. Georg Thieme Verlag Stuttgart. New York.
- Kim, Bo Ram,Lee, Hyung-Geun,Kang, Seung-Beom,Sung, Gi Hyeon,Kim, Jeum-Jong,Park, Jong Keun,Lee, Sang-Gyeong,Yoon, Yong-Jin
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experimental part
p. 42 - 50
(2012/03/26)
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- An efficient protocol for the amidation of carboxylic acids promoted by trimethyl phosphite and iodine
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A practical, one-pot protocol is described for the conversion of carboxylic acids into amides through carboxyl activation by the reagent combination of trimethyl phosphite and iodine. This method integrates several advantages: (1) it allows amines to be chemoselectively acylated with excellent results in the presence of sulfur and oxygen nucleophiles; (2) the method shows wide generality in respect of solvent, base, and substrate; (3) the reagents used are widely available and much less expensive than common coupling reagents, and (4) the process is remarkably convenient, permitting extraction, recrystallization, and column chromatography as optional work-up procedures. The chemoselectivity and generality of the method, the low cost, and wide availability of reagents combined with the ease of use make it a very favorable process.
- Luo, Qun-Li,Lv, Lina,Li, Yu,Tan, Jian-Ping,Nan, Wenhui,Hui, Qun
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supporting information; experimental part
p. 6916 - 6922
(2012/01/06)
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- Palladium-catalyzed C-C bond formation of arylhydrazines with olefins via carbon-nitrogen bond cleavage
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The unactivated carbon-nitrogen bond of various aryl hydrazines was cleaved under very mild conditions by Pd(0) with the assistance of Pd(II). The in situ generated aryl palladium complex readily takes part in the C-C bond formation with olefins. This study offered a new mode of C-Pd bond formation, which will spur the development of palladium-catalyzed cross-coupling in the future.
- Zhu, Ming-Kui,Zhao, Jun-Feng,Loh, Teck-Peng
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supporting information; experimental part
p. 6308 - 6311
(2012/01/06)
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- Oxindole synthesis by palladium-catalysed aromatic C-H alkenylation
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A strategy involving palladium-catalysed aromatic C-H functionalisation/ intramolecular alkenylation provides a convenient and direct synthesis of 3-alkylideneoxindoles. In the presence of 5 mol% of PdCl2MeCN 2 and AgOCOCF3, a wide variety of N-cinnamoylanilines gave 3-alkylideneoxindoles in moderate to good yield. The Royal Society of Chemistry.
- Ueda, Satoshi,Okada, Takahiro,Nagasawa, Hideko
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supporting information; experimental part
p. 2462 - 2464
(2010/08/13)
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- SmI3-catalyzed addition of amines to α,β-unsaturated N-acylbenzotriazoles
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The addition of amines to α,β-unsaturated N-acylbenzotriazoles could be catalyzed by samarium triiodide (SmI3) at ambient temperature. α,β-Unsaturated aliphatic N-acylbenzotriazoles afforded bis-addition products (β-amino amides), whereas N-cinnamoylbenzo
- Wang, Xiaoxia,He, Liang,Li, Zhifang,Wang, Wencun,Liu, Junhua
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experimental part
p. 819 - 829
(2009/08/08)
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- Rhodium-catalysed addition reaction of aryl- and alkenylboronic acids to isocyanates
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The addition reaction of aryl- and alkenylboronic acids to isocyanates is catalysed by a rhodium(i) complex, affording secondary amides under mild conditions. The Royal Society of Chemistry.
- Miura, Tomoya,Takahashi, Yusuke,Murakami, Masahiro
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p. 3577 - 3579
(2008/03/12)
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- A catalyst system for the formation of amides by reaction of carboxylic acids with blocked isocyanates
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A catalyst for the reaction of blocked isocyanates (blocking agent diisopropylamine and dimethyl pyrazole) and carboxylic acids was identified. Magnesium and in some instances calcium salts proved to be highly active as catalyst. This reaction gives amides in quantitative yield and excellent selectivity and is suitable for coating and general chemical purposes.
- Gertzmann,Gürtler
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p. 6659 - 6662
(2007/10/03)
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- Addition of organostannanes to isocyanate catalyzed by a rhodium complex
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Arylstannanes add to isocyanate in the presence of a rhodium catalyst to afford amides in good to excellent yields. Use of a phenol derivative as an additive is found to play an essential role for the successful reaction.
- Koike, Tooru,Takahashi, Masabumi,Arai, Nobumichi,Mori, Atsunori
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p. 1364 - 1365
(2007/10/03)
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- Efficient procedure for the preparation of amides using polymer-bound reagents
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An effective method for the conversion of acids into amides is presented. The two-step procedure includes the preparation of acid chloride intermediates using Pol-Ph3P and subsequent treatment of these intermediates with amines and polymer-bound base. The amides were accessible in high yields and purities without further purification.
- Buchstaller,Ebert,Anlauf
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p. 1001 - 1005
(2007/10/03)
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- Zeolite-HY : A selective and efficient catalyst for the synthesis of amides under microwave irradiations
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An efficient and selective method for the conversion of various acids into their corresponding amides in the presence of zeolite under microwave irradiation is described. The reaction proceeds efficiently at ambient pressure in high yields.
- Gadhwal, Sunil,Dutta, Manu Prakash,Boruah, Anima,Prajapati, Dipak,Sandhu, Jagir S.
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p. 725 - 727
(2007/10/03)
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- A facile one-pot transformation of carboxylic acids to amides
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Carboxylic acids, converted in situ into carboxylic-(p-nitrobenzene)sulfonic anhydrides using p-nitrobenzenesulfonyl chloride, Et3N, and DMAP in CH3CN, react with primary or secondary amines, to give amides in high yields.
- Lee,Cho,Lee,Cho
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p. 2877 - 2881
(2007/10/02)
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- Nucleophilic substitution reactions of cinnamoyl chlorides with anilines in acetonitrile and acetonitrile-methanol mixtures
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Kinetic studies on the solvolysis (in MeOH-MeCN mixtures) and aminolysis (with anilines in MeCN) of cinnamoyl chlorides have been carried out at 25.0 deg C.The relatively large negative values of ρY+ = -0.9 ca. -1.5 for the methanolysis are consistent with a dissociative SN2-like mechanism.For the aminolysis, the ρy values are positive (ρY = 0.52 ca. 1.64) and ρX values range from -1.68 to -2.51 in acetonitrile.The positive values of βX = 0.6-0.9 and ρXY = 0.88 in acetonitrile, and isotope effect data suggest that the aminolysis proceeds by a stepwise mechanism with rate-limiting breakdown of the tetrahedral intermediate, T+/-.It is noted that in the acyl-transfer reactions proceeding by rate-limiting departure of the leaving group from the tetrahedral intermediate the signs of both ρY and ρXY are positive and the reactivity-selectivity principle (RSP) is valid in general.
- Kim, Tae-Hyoung,Huh, Chul,Lee, Bon-Su,Lee, Ikchoon
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p. 2257 - 2262
(2007/10/03)
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