- Half-sandwich Ruthenium(II) Schiff base complexes: Synthesis, characterization and effective catalysts for one-pot conversion of aldehydes to amides
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Five new Schiff base ligands and conformationally rigid half-sandwich organo ruthenium(II) Schiff base complexes (1–5) with the general formula [Ru(η6?p?cymene)(Cl)(L1-5)] (where, L = mono anionic Schiff base ligands) have been synthesized from the reaction of [{(η6?p?cymene)RuCl}2(μ?Cl)2] with a bidentate Schiff bases ligands. These ruthenium(II) Schiff base complexes were fully characterized by elemental analysis, FT?IR, UV–Vis, 1H & 13C NMR and mass spectroscopy studies. In chloroform solution, all the metal complexes exhibit characteristic metal to ligand charge transfer bands (MLCT) and emission bands in the visible region. The crystal structure of the complexes [Ru(η6?p?cymene)(Cl)(L1)] (1) and [Ru(η6?p?cymene)(Cl)(L3)] (3) were determined by single crystal X?ray crystallography. The complexes exhibited good catalytic activity for aldehydes to amides by one-pot conversion process in the presence of NaHCO3/NH2OH·HCl.
- Premkumar, Muniyappan,Vijayan, Paranthaman,Venkatachalam, Galmari
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Read Online
- Kinetic dependence of the aqueous reaction of N-(hydroxymethyl)benzamide derivatives upon addition of electron-withdrawing groups.
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[figure: see text] The rate constants for the hydronium ion, hydroxide, and water-catalyzed breakdown of N-(hydroxymethyl)benzamide (1), 4-chloro-N-(hydroxymethyl)benzamide (2), and 2,4-dichloro-N-(hydroxymethyl)benzamide (3) in H2O, at 25 degrees C, I = 1.0 (KCl), have been determined. The reactions of 1, 2, and 3 were found to be specific acid and specific base catalyzed with a first-order dependence on hydronium and hydroxide ions. At higher hydroxide concentrations, the reactions were found to be pH independent for each compound studied.
- Tenn 3rd.,French,Nagorski
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Read Online
- Acid-promoted palladium(II)-catalyzed ortho-halogenation of primary benzamides: En route to halo-arenes
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Br?nsted acid-promoted palladium(II)-catalyzed regioselective installation of halogens (Br, Cl, and I) to the aromatic ring of benzamide derivatives has been achieved using primary amides. A wide variety of benzamides were compatible under established conditions to afford the halogenated products without installing any external auxiliary. Mild reaction conditions, use of primary amide as a directing group, external additive-free conditions, and gram-scale reaction are some appealing features of this protocol. Detailed experimental results revealed that Br?nsted acid plays a critical role in this transformation.
- Jaiswal, Yogesh,Kumar, Amit
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- Method for efficient solid-phase synthesis of amide derivative through carboxylic acid and urea
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The invention discloses a method for efficient solid-phase synthesis of an amide derivative through carboxylic acid and urea. The method comprises the steps that a carboxylic acid and urea mixture anda catalyst are mixed, a mixture is placed in a sealed pipe of a single-mode microwave device and heated, then through a monitoring reaction endpoint, namely the ratio, being 4:1, of cyclohexane to ethyl acetate in thin-layer chromatography (TLC), reactants are cooled to the room temperature, extraction is conducted through the ethyl acetate, then an extract is sequentially washed by hydrochloricacid, a sodium bicarbonate solution and water, an organic layer is dried by anhydrous magnesium sulfate, a solvent is subjected to decompressed distillation, and thus the amide derivative is obtained.Benzoic acid and the urea are mixed and heated for a long time at 220 DEG C, a chemical reaction can be completed only within 20-80 seconds by applying a microwave assistive technology, and the effect higher than the effect achieved by conventional heating is achieved. By applying a solvent-free solid phase method and utilizing an easy-to-obtain reagent, high-yield amide is prepared through a simple and effective method, and the solvent-free solid phase method has the advantages of high reaction speed, low catalyst cost and the like.
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Paragraph 0022-0030
(2019/11/12)
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- Development and Utilization of a Palladium-Catalyzed Dehydration of Primary Amides to Form Nitriles
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A palladium(II) catalyst, in the presence of Selectfluor, enables the efficient and chemoselective transformation of primary amides into nitriles. The amides can be attached to aromatic rings, heteroaromatic rings, or aliphatic side chains, and the reactions tolerate steric bulk and electronic modification. Dehydration of a peptaibol containing three glutamine groups afforded structure-activity relationships for each glutamine residue. Thus, this dehydration can act similarly to an alanine scan for glutamines via synthetic mutation.
- Al-Huniti, Mohammed H.,Rivera-Chávez, José,Colón, Katsuya L.,Stanley, Jarrod L.,Burdette, Joanna E.,Pearce, Cedric J.,Oberlies, Nicholas H.,Croatt, Mitchell P.
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supporting information
p. 6046 - 6050
(2018/09/27)
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- Design, synthesis, DFT study and antifungal activity of the derivatives of pyrazolecarboxamide containing thiazole or oxazole ring
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Pyrazolecarboxamide fungicides are one of the most important classes of agricultural fungicides, which belong to succinodehydrogenase inhibitors (SDHIS). To discover new pyrazolecarboxamide analogues with broad spectrum and high activity, a class of new compounds of pyrazole carboxamide derivatives containing thiazole or oxazole ring were designed by scaffold hopping and bioisosterism, and 36 pyrazole carboxamide derivatives with antifungal activity were synthesized. Those compounds were evaluated against five phytopathogenic fungi, Gibberella zeae, Phytophythora capsici, Sclerotonia sclerotiorum, Erysiphe graminis and Puccinia sorghi. The results indicated that most of the compounds displayed good fungicidal activities, especially against E. graminis. Theoretical calculations were carried out at the B3LYP/6-31G (d, p) level and the full geometry optimization was carried out using the 6-31G (d, p) basis set, and the frontier orbital energy, atomic net charges, molecular docking were discussed, and the structure-activity relationships were also studied.
- Yan, Zhongzhong,Liu, Aiping,Huang, Mingzhi,Liu, Minhua,Pei, Hui,Huang, Lu,Yi, Haibo,Liu, Weidong,Hu, Aixi
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p. 170 - 181
(2018/03/08)
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- Tandem synthesis of aromatic amides from styrenes in water
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An expedient one-pot synthesis of aromatic amides has been reported from styrenes in the presence of N-bromosuccinimide and iodine by using aqueous ammonia in water. The reaction proceeds through the formation of α-bromoketone as an intermediate in the pr
- Sathe, Pratima A.,Karpe, Aniket S.,Parab, Aniket A.,Parade, Babasao S.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
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supporting information
p. 2820 - 2823
(2018/06/25)
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- Metal-Free Thermal Activation of Molecular Oxygen Enabled Direct α-CH2-Oxygenation of Free Amines
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Direct oxidation of α-CH2 group of free amines is hard to achieve due to the higher reactivity of amine moiety. Therefore, oxidation of amines involves the use of sophisticated metallic reagents/catalyst in the presence or absence of hazardous oxidants under sensitive reaction conditions. A novel method for direct C-H oxygenation of aliphatic amines through a metal-free activation of molecular oxygen has been developed. Both activated and unactivated free amines were oxygenated efficiently to provide a wide variety of amides (primary, secondary) and lactams under operationally simple conditions without the aid of metallic reagents and toxic oxidants. The method has been applied to the synthesis of highly functionalized amide-containing medicinal drugs, such as O-Me-alibendol and -buclosamide.
- Ghosh, Santanu,Jana, Chandan K.
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p. 260 - 266
(2018/02/19)
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- A selective hydration of nitriles catalysed by a Pd(OAc)2-based system in water
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In situ formation of a [Pd(OAc)2bipy] (bipy = 2,2′-bipyridyl) complex in water selectively catalyses the hydration of a wide range of organonitriles at 70 °C. Catalyst loadings of 5 mol% afford primary amide products in excellent yields in the absence of hydration-promoting additives such as oximes and hydroxylamines.
- Sanz Sharley, Daniel D.,Williams, Jonathan M.J.
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supporting information
p. 4090 - 4093
(2017/09/27)
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- A 4, 6 - double-halogenated isophthalonitrile preparation method (by machine translation)
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The present invention relates to the technical field of the synthesis of pharmaceutical intermediates, in particular to a 4, 6 - double-halogenated isophthalonitrile preparation method, through the use of cheap and easily obtained 2, 4 - double-halo benzoic acid as the raw material, the reaction of the halide, the amidation reaction, dehydration reaction, the nitration reaction, reduction reaction, the diazotization reaction, the substitution reaction for the synthesis of 4, 6 - double-halogenated isophthalonitrile; the total yield can be 21.5%. The process route is easily obtained and cheap materials, few by-products, the purification treatment is the process is simple, easy to realize industrial production. (by machine translation)
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- Heteropolytungstostannate as a homo- and heterogeneous catalyst for Knoevenagel condensations, selective oxidation of sulfides and oxidative amination of aldehydes
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Heteropolytungstostannate K11H[P2W18O68(HOSnIVOH)3]·20H2O (1) is used as a homo- and heterogeneous catalyst for Knoevenagel condensations. New Fe3O4@SiO2@CH2(CH2)2NH3+[P2W18O68(HOSnIVOH)3]11- nanocatalyst was fabricated through electrostatic grafting of (1) on amine-modified silica-coated magnetic nanoparticles. The new magnetically recoverable nanocatalyst was characterized using infrared spectroscopy (IR), scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray powder diffractometry (XRD), energy-dispersive X-ray analysis (EDX) and alternating gradient force magnetometry (AGFM). The results indicate that the particles are mostly spherical in shape and have an average size of approximately 30 nm. The catalytic activity of the catalyst was investigated in the selective oxidation of sulfides to sulfoxides and oxidative amination of aldehydes in an aqueous medium. The catalyst was reused at least five times without significant decrease in catalytic activities, and the structure of the catalyst remained unchanged after recycling.
- Khoshnavazi, Roushan,Bahrami, Leila,Rezaei, Manuchehr
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p. 45495 - 45503
(2017/10/06)
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- One–pot green catalytic synthesis of primary amides in aqueous medium by CuII–immobilized silica–based magnetic retrievable nanocatalyst
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In order to develop a new nanocatalyst, a copper–birhodanine derivative complex crafted onto Fe3O4@SiO2nanoparticle [abbreviated as Fe3O4@SiO2–Ligand–Cu(II)] was synthesized and their structure characterized by different physicochemical techniques such as FT–IR, FE–SEM, XRD, EDX, TGA, AGFM, and ICP. This new magnetic nanoparticle revealed high catalytic performance for one–pot green synthesis of primary amides from aldehydes and NH2OH·HCl in water as a green solvent. The effects of catalyst amounts, reaction temperature, various bases and type of solvent on catalytic activity were also investigated. The catalyst was retrieved eight times without significant loss of its catalytic activity.
- Rezaei, Manuchehr,Amani, Kamal,Darvishi, Kamran
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- A mild hydration of nitriles catalysed by copper(ii) acetate
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A simple, mild and general procedure for the hydration of nitriles to amides using copper as catalyst and promoted by N,N-diethylhydroxylamine is described. The reaction can be conducted in water at low temperature in short reaction times. This new procedure allows amides to be obtained from a wide range of substrates in excellent yields.
- Marcé, Patricia,Lynch, James,Blacker, A. John,Williams, Jonathan M. J.
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supporting information
p. 1436 - 1438
(2016/01/25)
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- Design, synthesis and fungicidal activity of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide
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To find a new lead compound with high biological activity, a series of N-substituted benzoyl-1,2,3,4-tetrahydroquinolyl-1-carboxamide were designed using linking active substructures method. The target compounds were synthesized from substituted benzoic acid by four steps and their structures were confirmed by 1H NMR, IR spectrum and elemental analysis. The in vitro bioassay results indicated that some target compounds exhibited excellent fungicidal activities, and the position of the substituents played an important role in fungicidal activities. Especially, compound 5n, exhibited better fungicidal activities than the commercial fungicide flutolanil against two tested fungi Valsa Mali and Sclerotinia sclerotiorum, with EC50 values of 3.44 and 2.63 mg/L, respectively. And it also displayed good in vivo fungicidal activity against S. sclerotiorum with the EC50 value of 29.52 mg/L.
- Lei, Peng,Xu, Yan,Du, Juan,Yang, Xin-Ling,Yuan, Hui-Zhu,Xu, Gao-Fei,Ling, Yun
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p. 2544 - 2546
(2016/07/07)
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- Synthesis, antitumor activity and mechanism of action of novel 1,3-thiazole derivatives containing hydrazide–hydrazone and carboxamide moiety
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A series of novel 2,4,5-trisubstituted 1,3-thiazole derivatives containing hydrazide–hydrazine, and carboxamide moiety including 46 compounds T were synthesized, and evaluated for their antitumor activity in vitro against a panel of five human cancer cell lines. Eighteen title compounds T displayed higher inhibitory activity than that of 5-Fu against MCF-7, HepG2, BGC-823, Hela, and A549 cell lines. Especially, T1, T26 and T38 exhibit best cytotoxic activity with IC50values of 2.21?μg/mL, 1.67?μg/mL and 1.11?μg/mL, against MCF-7, BCG-823, and HepG2 cell lines, respectively. These results suggested that the combination of 1,3-thiazole, hydrazide–hydrazone, and carboxamide moiety was much favorable to cytotoxicity activity. Furthermore, the flow cytometry analysis revealed that compounds T1 and T38 could induce apoptosis in HepG2 cells, and it was confirmed T38 led the induction of cell apoptosis by S cell-cycle arrest.
- He, Haifeng,Wang, Xiaoyan,Shi, Liqiao,Yin, Wenyan,Yang, Ziwen,He, Hongwu,Liang, Ying
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p. 3263 - 3270
(2016/07/12)
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- Iodine-catalyzed oxidative C-C bond cleavage for benzoic acids and benzamides from alkyl aryl ketones
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Iodine-catalyzed oxidative C-C bond cleavage has been performed for the facile synthesis of both benzoic acids and benzamides from readily available alkyl aryl ketones. Additionally benzylidene acetones and phenylacetylenes were also converted to the corresponding aromatic acids under the same conditions. This approach features the use of inexpensive iodine as a catalyst, broad substrate scope and open air conditions.
- Sathyanarayana, Pochampalli,Upare, Atul,Ravi, Owk,Muktapuram, Prathap Reddy,Bathula, Surendar Reddy
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p. 22749 - 22753
(2016/03/15)
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- Aminofluorene-Mediated Biomimetic Domino Amination-Oxygenation of Aldehydes to Amides
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A conceptually novel biomimetic strategy based on a domino amination-oxygenation reaction was developed for direct amidation of aldehydes under metal-free conditions employing molecular oxygen as the oxidant. 9-Aminofluorene derivatives acted as pyridoxamine-5′-phosphate equivalents for efficient, chemoselective, and operationally simple amine-transfer oxygenation reaction. Unprecedented RNH transfer involving secondary amine to produce secondary amides was achieved. In the presence of 18O2, 18O-amide was formed with excellent (95%) isotopic purity.
- Ghosh, Santanu,Jana, Chandan K.
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supporting information
p. 5788 - 5791
(2016/11/29)
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- Synthesis and bioactivity of novel pyrazole oxime derivatives containing oxazole ring
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Abstract A series of novel pyrazole oxime derivatives containing oxazole ring were designed and synthesized. The title compounds were structurally confirmed by 1H NMR, 13C NMR spectra and elemental analyses. Preliminary bioassay results showed that some of the title compounds displayed promising fungicidal activity besides insecticidal and acaricidal activity. Particularly, compound 8c exhibited potent fungicidal activity against cucumber Pseudoperonospora cubensis beyond good insecticidal activity against Aphis craccivora and Nilaparvata lugens.
- Wang, Sen-Lin,Shi, Yu-Jun,He, Hai-Bing,Li, Yu,Li, Yang,Dai, Hong
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p. 672 - 674
(2015/08/03)
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- Molecular iodine-mediated domino reaction for the synthesis of benzamides, 2,2-Diazidobenzofuran-3(2H)-ones and benzoxazolones
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A simple and efficient domino protocol has been developed for the preparation of biologically important benzamides, 2,2-diazidobenzofuran-3(2H)- ones and benzoxazolones from various structurally and electronically divergent acetophenones and ortho-hydroxyacetophenones in the presence of molecular iodine, sodium azide and sodium bicarbonate at 100 °C in good to excellent yields. Copyright
- Rajendar,Kant, Ruchir,Narender
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supporting information
p. 3591 - 3596
(2014/01/06)
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- Ruthenium-catalyzed rearrangement of aldoximes to primary amides in water
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The rearrangement of aldoximes to primary amides has been studied using the readily available arene-ruthenium(II) complex [RuCl2(η 6-C6Me6){P(NMe2)3}] (5 mol %) as catalyst. Reactions proceeded cleanly in pure water at 100 °C without the assistance of any cocatalyst, affording the desired amides in high yields (70-90%) after short reaction times (1-7 h). The process was operative with both aromatic, heteroaromatic, α,β-unsaturated, and aliphatic aldoximes and tolerated several functional groups. Reaction profiles and experiments using 18O-labeled water indicate that two different mechanisms are implicated in these transformations. In both of them, nitrile intermediates are initially formed by dehydration of the aldoximes. These intermediates are then hydrated to the corresponding amides by the action of a second molecule of aldoxime or water. A kinetic analysis of the rearrangement of benzaldoxime to benzamide is also discussed.
- Garcia-Alvarez, Rocio,Diaz-Alvarez, Alba E.,Borge, Javier,Crochet, Pascale,Cadierno, Victorio
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p. 6482 - 6490
(2012/10/30)
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- Highly efficient one-pot synthesis of primary amides catalyzed by scandium(III) triflate under controlled MW
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The present Letter highlights a versatile synthetic protocol for the one-pot synthesis of primary amides employing scandium(III) triflate as a catalyst in water under controlled MW. This methodology offers excellent yields in shorter reaction times with enhanced selectivity.
- Allam, Bharat Kumar,Singh, Krishna Nand
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experimental part
p. 5851 - 5854
(2011/12/03)
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- Formamide as an ammonia synthon in amination of acid chlorides
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The use of formamide as a convenient source of ammonia has been explored for the direct transformation of acid chlorides to primary amides. Various aliphatic, alicyclic aromatic, and heterocyclic acid chlorides are converted to the corresponding carboxamides in good yields (75-94%). Copyright Taylor & Francis Group, LLC.
- Srinivasan,Manisankar
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experimental part
p. 3538 - 3543
(2011/02/22)
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- Amidates as leaving groups: Structure/reactivity correlation of the hydroxide-dependent E1cB-like breakdown of carbinolamides in aqueous solution
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(Graph Presented) The kinetic study of the aqueous reaction, between pH 10 and 14, of eight N-(hydroxymethyl)benzamide derivatives in water at 25°C, I = 1.0 M (KCl), has been performed. In all cases, the reaction proceeds via a specific-base-catalyzed deprotonation of the hydroxyl group followed by rate-limiting breakdown of the alkoxide to form aldehyde and amidate (E1cB-like). Such a mechanism was supported by the lack of general buffer catalysis and the first-order dependence of the rate of reaction at low hydroxide concentrations and the transition to zero-order dependence on hydroxide at high concentration. A ρ-value of 0.67 was found for the Hammett correlation between the maximum rate for the hydroxide independent breakdown of the deprotonated carbinolamide (k1) and the substituent on the aromatic ring of the title compounds. Conversely, the substituents on the aromatic ring of the amide portion of the carbinolamide had only a small effect on the Ka of the hydroxyl group indicating that the amide group does not strongly transmit the electronic information of the substituents. These observations led to the conclusion that the major effect of electronic changes on the amide of carbinolamides is reflected in the nucleofugality of the amidate once the alkoxide is formed and not in the pKa of the hydroxyl group of the carbinolamide.
- Tenn III, William J.,Murphy, John L.,Bim-Merle, Jessica K.,Brown, Jason A.,Junia, Adam J.,Price, Malea A.,Nagorski, Richard W.
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p. 6075 - 6083
(2008/02/10)
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- Iridium-catalyzed conversion of alcohols into amides via oximes
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(Chemical Equation Presented) The iridium catalyst [Ir(Cp*)Cl 2]2 is effective for the rearrangement of oximes to furnish amides. The reaction has been combined with catalytic transfer hydrogenation between an alcohol and alkene to allow the conversion of alcohols into amides in a one-pot process.
- Owston, Nathan A.,Parker, Alexandra J.,Williams, Jonathan M. J.
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- Highly efficient ruthenium-catalyzed oxime to amide rearrangement
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A wide range of aldoximes has been converted into the corresponding amides using the ruthenium-based catalyst Ru(PPh3)3(CO)H 2/dppe/ TsOH. The amides are generated in high yield and selectivity, with catalyst loading as low as 0.04 mol %.
- Owston, Nathan A.,Parker, Alexandra J.,Williams, Jonathan M. J.
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p. 3599 - 3601
(2008/02/12)
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- Cannizzaro-type disproportionation of aromatic aldehydes to amides and alcohols by using either a stoichiometric amount or a catalytic amount of lanthanide compounds
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Aromatic aldehydes can be directly converted to the corresponding amides and alcohols in good to excellent yields by the treatment of aromatic aldehydes with lithium amide LiN(SiMe3)2 in the presence of catalytic lanthanide chlorides LnCIs or by the treatment of aromatic aldehydes with a stoichiometric amount of lanthanide amides [(Me3Si)2N]3Ln(μ-Cl) Li(THF)3 at ambient temperature. The effects of solvents, substitutents on the phenyl ring, and lanthanide metals on the reaction have been examined. The mechanism of the disproportionation reaction was proposed based on the experimental results.
- Zhang, Lijun,Wang, Shaowu,Zhou, Shuangliu,Yang, Gaosheng,Sheng, Enhong
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p. 3149 - 3153
(2007/10/03)
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- Pyrazolo-[1,5-a]-1,3,5-triazine corticotropin-releasing factor (CRF) receptor ligands
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The syntheses and rat CRF receptor binding affinities of 'retro-pyrazolotriazine' corticotropin-releasing factor (CRF) ligands 4 are reported. Some have high affinity for rat CRF receptors (Ki≤10 nM). The data provide additional support for the hypothesis that it is possible to interchange isosteric cores with similar electronic properties in the design of high-affinity CRF receptor ligands, provided the peripheral pharmacophore elements are maintained in the same three-dimensional array.
- Gilligan, Paul J.,Folmer, Beverly K.,Hartz, Richard A.,Koch, Stephanie,Nanda, Kausik K.,Andreuski, Stephen,Fitzgerald, Lawrence,Miller, Keith,Marshall, William J.
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p. 4093 - 4102
(2007/10/03)
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- Hydrogen peroxide oxidation of N,N-dimethylhydrazones promoted by selenium compounds, titanosilicalites or acetonitrile
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Hydrogen peroxide oxidation of N,N-dimethylhydrazones 1 promoted by title reagents has been investigated. Depending on the substrate nitrile 2 and/or amide 3 accompanied with carboxylic acid 4 and parent carbonyl compounds 5 were obtained. Formation of nitriles 2 with H2O2-acetonitrile system is limited for a few more active substrates. The mechanism of the reaction, based on generated in situ peroxyiminoacetic acid, is presented. A broad spectrum of aliphatic, unsaturated and aromatic nitriles 2 was obtained by oxidation of corresponding N,N-dimethylhydrazones 1 with hydrogen peroxide in the presence of poly(bis-9,10-anthracenyl) diselenide (PADS) (7) as catalyst.
- Giurg,Mlochowski,Ambrozak
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p. 1713 - 1720
(2007/10/03)
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- A Mild and Convenient Oxidation of Aryl Nitriles to Aryl Amides by Aqueous Sodium Perborate
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A series of benzonitriles has been reacted with sodium perborate in water and a cosolvent to produce the corresponding amides in good yield.The procedure is a mild and convenient alternative for the synthesis of aryl amides.
- Reed, Kathryn L.,Gupton, John T.,Solarz, Traci L.
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p. 563 - 571
(2007/10/02)
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- Reaction of disubstituted sulfur diimides with CH acids.
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Derivatives of 1,3,4-oxathiazole were obtained by the reaction of N,N'-diaroylsulfur diimides with acetylacetone, dibenzoylmethane, and 5,5-dimethyl-1,3-cyclohexanedione.
- Levchenko, E. S.,Budnik, L. V.,Kalinin, V. N.,Kisilenko, A. A.
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p. 2249 - 2251
(2007/10/02)
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