- MODIFIED PROTEINS AND PROTEIN DEGRADERS
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Provided herein are compounds, pharmaceutical compositions, and methods for binding or degrading target proteins. Further provided herein are compounds having a DNA damage-binding protein 1 (DDB1) binding moiety. Some such embodiments include a linker. Some such embodiments include a target protein binding moiety. Further provided herein are ligand-DDB1 complexes. Further provided herein are in vivo modified DDB1 proteins.
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Paragraph 00785; 00788; 00789
(2021/12/08)
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- Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition
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Synthesis of amides via Beckmann rearrangement of ketoximes promoted by cyanuric chloride (TCT)/DMSO under mild conditions has been reported. Conditions of the Beckmann rearrangement, e.g., solvents, the ratios of TCT/DMSO, and the temperature, were investigated using diphenylmethanone oxime as a substrate. The optimized conditions were adopted to afford fourteen amides with yields ranging from 20% to 99%. A plausible mechanism involving an active dimethyl alkoxysulfonium intermediate was proposed according to the mass spectrometry analysis. To our best knowledge, this is the first case of study on Beckmann rearrangement of ketoximes promoted by TCT/DMSO under a mild condition to afford amides efficiently.
- Ma, Ruonan,Chen, Xueyuan,Xiao, Zhiyin,Natarajan, Mookan,Lu, Chunxin,Jiang, Xiujuan,Zhong, Wei,Liu, Xiaoming
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supporting information
(2021/01/06)
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- Dehydrative Beckmann rearrangement and the following cascade reactions
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The Beckmann rearrangement has been predominantly studied for the synthesis of amide and lactam. By strategically using the in situ generated Appel's salt or Mitsunobu's zwitterionic adduct as the dehydrating agent, a series of Beckmann rearrangement and following cascade reactions have been developed herein. The protocol allows the conversion of various ketoximes into amide, thioamide, tetrazole and imide products in modular procedures. The generality and tolerance of functionalities of this method have been demonstrated.
- Liu, Yinghui,Wei, Yongjiao,Xie, Lan-Gui
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supporting information
(2021/11/16)
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- Hypervalent Iodine Reagent-Promoted Hofmann-Type Rearrangement/Carboxylation of Primary Amides
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A novel transformation of primary amides to secondary amides promoted by hypervalent iodine reagents was developed. The hypervalent iodine reagent-mediated Hofmann-type rearrangement generated an isocyanate intermediate, which was subsequently trapped by an in situ generated carboxylic acid from the hypervalent iodine reagent to provide the corresponding secondary amides. This method provided a facile and efficient route for the synthesis of secondary amides from primary amides and also revealed novel reactivities of hypervalent iodine reagents.
- Wang, Xia,Yang, Peng,Hu, Bo,Zhang, Qian,Li, Dong
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p. 2820 - 2826
(2021/02/01)
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- Zinc(II)-Catalyzed Synthesis of Secondary Amides from Ketones via Beckmann Rearrangement Using Hydroxylamine-O-sulfonic Acid in Aqueous Media
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A zinc(II)-catalyzed single-step protocol for the Beckmann rearrangement using hydroxylamine-O-sulfonic acid (HOSA) as the nitrogen source in water was developed. This direct method efficiently produces secondary amides under open atmosphere in a pure form after basic aqueous workup. It isenvironmentally benign and operationally simple.
- Verma, Saumya,Kumar, Puneet,Khatana, Anil K.,Chandra, Dinesh,Yadav, Ajay K.,Tiwari, Bhoopendra,Jat, Jawahar L.
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p. 3272 - 3276
(2020/11/02)
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- Direct synthesis of secondary amides from ketones through Beckmann rearrangement using O-(mesitylsulfonyl)hydroxylamine
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The Beckmann rearrangement is a versatile method for the preparation of secondary amides from ketones via oxime intermediates and has been widely used in the synthesis of bioactive natural products and pharmaceuticals. Herein, we have developed a highly efficient direct method for the preparation of secondary amides and lactams from ketones using O-(mesitylsulfonyl)hydroxylamine (MSH). The reactions proceed rapidly at room temperature under mild condition without requiring any additive, and tolerate multiple functional groups. A simple aqueous work-up often furnished the products in excellent yield with high purity.
- Chandra, Dinesh,Verma, Saumya,Pandey, Chandra Bhan,Yadav, Ajay K.,Kumar, Puneet,Tiwari, Bhoopendra,Jat, Jawahar L.
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supporting information
(2020/03/23)
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- Hydrative syntheses of amides from alkynes catalyzed by an Au(I) complex containing pyridyl-functionalized NHC ligand
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An Au(I)-NHC complex [L1AuBr] (1) with appended pyridyl group on the ligand scaffold is synthesized and its catalytic efficacy for the direct synthesis of the amide from alkyne and sodium azide in acidic water is evaluated. Catalyst 1 readily converts a wide range of internal and terminal alkynes to the corresponding amides with low catalyst loading in TFA/DCE (2 mL, 1:1 v/v) at room temperature in short reaction time (2 h) and without the use of Ag(I) additive. A related catalyst that is devoid of the pyridyl fragment displays significantly lower activity illustrating the role of the promoter ligand for water activation. Mechanistic studies reveal an initial alkyne hydration to ketone followed by the Schmidt reaction to afford the amide.
- Singh, Kuldeep,Pal, Nilay Kumar,Guha, Chirajyoti,Bera, Jitendra K.
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- SO2F2-Activated Efficient Beckmann Rearrangement of Ketoximes for Accessing Amides and Lactams
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A novel, mild and practical protocol for the efficient activation of the Beckmann rearrangement utilizing the readily available and economical sulfuryl fluoride (SO2F2 gas) has been developed. The substrate scope of the operationally simple methodology has been demonstrated by 37 examples with good to nearly quantitative isolated yields (over 90 % yield in most cases) in a short time, including B(OH)2, COOH, NH2, and OH substituted substrates. A tentative mechanism was proposed involving formation and elimination of key intermediate, sulfonyl ester.
- Zhang, Guofu,Zhao, Yiyong,Xuan, Lidi,Ding, Chengrong
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supporting information
p. 4911 - 4915
(2019/07/31)
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- Polystyrene-supported phosphine oxide-catalysed Beckmann rearrangement of ketoximes in 1,1,1,3,3,3-hexafluoro-2-propanol
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A polystyrene-supported phosphine oxide-catalysed Beckmann rearrangement of ketoximes in 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) has been developed. Good substrate compatibility, mild reaction conditions, good yields as well as the reusability of the catalyst/solvent made this procedure more environmentally benign.
- Wang, Yaoyao,Chen, Qun,He, Mingyang,Wang, Liang
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p. 210 - 214
(2018/12/04)
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- Synthesis of diverse libraries of carboxamides via chemoselective N-acylation of amines by carboxylic acids employing Br?nsted acidic IL [BMIM(SO3H)][OTf]
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Chemoselective N-acylation of amines with carboxylic acids as acyl electrophiles and Br?nsted acidic IL [BMIM(SO3H)][OTf] as promoter is reported under both thermal and microwave irradiation to produce libraries of carboxamides in good to excellent yields after a simple workup. The protocol is compatible with structurally diverse 1° and 2° amines and works in the presence of sensitive functional groups such as thiols and phenols. The potential for recycling and reuse of the IL is also demonstrated.
- Savanur, Hemantkumar M.,Malunavar, Shruti S.,Prabhala, Pavankumar,Sutar, Suraj M.,Kalkhambkar, Rajesh G.,Laali, Kenneth K.
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supporting information
(2019/09/30)
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- Scope and mechanism of a true organocatalytic beckmann rearrangement with a boronic acid/perfluoropinacol system under ambient conditions
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Catalytic activation of hydroxyl functionalities is of great interest for the production of pharmaceuticals and commodity chemicals. Here, 2-alkoxycarbonyl- and 2-phenoxycarbonyl-phenylboronic acid were identified as efficient catalysts for the direct and chemoselective activation of oxime N-OH bonds in the Beckmann rearrangement. This classical organic reaction provides a unique approach to prepare functionalized amide products that may be difficult to access using traditional amide coupling between carboxylic acids and amines. Using only 5 mol % of boronic acid catalyst and perfluoropinacol as an additive in a polar solvent mixture, the operationally simple protocol features mild conditions, a broad substrate scope, and a high functional group tolerance. A wide variety of diaryl, aryl-alkyl, heteroaryl-alkyl, and dialkyl oximes react under ambient conditions to afford high yields of amide products. Free alcohols, amides, carboxyesters, and many other functionalities are compatible with the reaction conditions. Investigations of the catalytic cycle revealed a novel boron-induced oxime transesterification providing an acyl oxime intermediate involved in a fully catalytic nonself-propagating Beckmann rearrangement mechanism. The acyl oxime intermediate was prepared independently and was subjected to the reaction conditions. It was found to be self-sufficient; it reacts rapidly, unimolecularly without the need for free oxime. A series of control experiments and 18O labeling studies support a true catalytic pathway involving an ionic transition structure with an active and essential role for the boronyl moiety in both steps of transesterification and rearrangement. According to 11B NMR spectroscopic studies, the additive perfluoropinacol provides a transient, electrophilic boronic ester that is thought to serve as an internal Lewis acid to activate the ortho-carboxyester and accelerate the initial, rate-limiting step of transesterification between the precatalyst and the oxime substrate.
- Mo, Xiaobin,Morgan, Timothy D. R.,Ang, Hwee Ting,Hall, Dennis G.
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supporting information
p. 5264 - 5271
(2018/04/24)
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- METHOD FOR PRODUCING AMIDE COMPOUND
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PROBLEM TO BE SOLVED: To provide a novel method for producing an amide compound which does not require severe reacting conditions without directly using hydroxylamine and its derivative. SOLUTION: There is provided a method for producing an amide compound which comprises: a step of transferring a ketone compound and an oxime compound to oxime in the presence of an organic solvent and an acid catalyst; and a step of subjecting the oxime to Beckmann rearrangement. The acid catalyst preferably is hydrochloric acid, sulfuric acid, methanesulfonic acid, tosyl acid monohydrate, trifluoromethanesulfonic acid, bistrifluoromethane sulfonimide, a boron trifluoride-diethyl ether complex, scandium trifluoromethanesulfonate (III), iron trifluoromethanesulfonate (III), copper trifluoromethanesulfonate (II), bismuth(III) trifluoromethanesulfonate, titanium tetrachloride or iron trichloride. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT
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Paragraph 0029; 0031
(2018/09/30)
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- COLORING COMPOSITION, INKJET INK, AND TEXTILE PRINTING METHOD
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PROBLEM TO BE SOLVED: To provide: a coloring composition excellent in cyan optical density (OD value) and light fastness, an inkjet ink containing the coloring composition, and a textile printing method using the coloring composition or the inkjet ink. SOLUTION: The invention provides: a coloring composition containing a compound represented by the general formula (1) described in the specification; an inkjet ink containing the coloring composition; and a textile printing method using the coloring composition or the inkjet ink. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
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Paragraph 0167-0169
(2017/10/13)
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- The highly efficient Beckmann rearrangement of ketoximes to amides by using Mukaiyama reagent under mild conditions
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Background: A rapid and efficient synthesis of amides via Beckmann rearrangement of ketoximes with good to excellent yields has been carried out using Mukaiyama reagent/Et3N system. The procedure is mild and suitable for both aromatic and cycloaliphatic substrates affording the products in good to quantitative yields with short reaction times. Methods: A suspension of acetophenone oxime (0.135 g, 1 mmol), Mukaiyama reagent (0.383 g, 1.5 mmol), and Et3N (0.21 mL, 1.5 mmol) in CH3CN (3 mL) was magnetically stirred at room temperature. After completion of the reaction (monitored by TLC) and evaporation of CH3CN, aqueous HCl (5%, 10 mL) was added and the organic layer extracted with CH2Cl2 (3 × 5 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated. Purification of the crude product by short column chromatography on silica gel (n-hexane/EtOAc, 5/2) provided N-phenylacetamide (0.120 g, 89%) as a white solid: mp 112°C (lit. 113-115°C); 1H NMR (CDCl3, 250 MHz) 8.03 (brs, 1H), 7.52 (d, J=8.0 Hz, 2H), 7.28 (t, J=7.8 Hz, 2H), 7.09 (t, J=7.4 Hz, 1H), 2.15 (s, 3H). Results: In a continuation of our studies on the use of the Mukaiyama reagent in organic transformations, we became interested in evaluating it as a reagent in the presence of triethylamine as a base for the conversion of ketoximes into corresponding N-substituted amides under mild conditions. To optimize the reaction conditions and find the best base and solvent using benzophenone oxime as a model substrate, a few experiments were carried out with Mukaiyama reagent and various bases and solvents at room temperature. The optimum conditions of reaction involved benzophenone oxime (1 mmol), Mukaiyama reagent (1.5 mmol), triethylamine (1.5 mmol), CH3CN (3 mL) at room temperature. Under the optimized conditions, a series of N-substituted amides were studied to establish the scope and limitations of this method. A wide range of substituted ketoximes derived from various aromatic, cycloaliphatic, and heterocyclic ketoximes gave desired products in good to excellent yields. Conclusion: We have disclosed a mild procedure for obtaining amides from the corresponding ketoximes via Beckmann rearrangement using Mukaiyama reagent. Among the attractive features of this protocol are its use of inexpensive and commercially available reagent, mild reaction conditions, simplicity, general applicability, relatively short reaction time, high yield and good selectivity.
- Azadi, Roya,Shams, Leila
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p. 141 - 145
(2017/03/30)
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- Synthesis of secondary amides from N-Substituted amidines by tandem oxidative rearrangement and isocyanate elimination
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In this work an efficient tandem process transforming N-substituted amidines into secondary amides has been described. The process involves N-acylurea formation by reaction of the substrate with bis(acyloxy)(phenyl)-λ3-iodane followed by isocyanate elimination. The periodinane reagents are obtained from the commercially available phenyl-iodine(III) diacetate [PhI(OAc)2, (PIDA)] by ligand exchange with carboxylic acids. The N-substituted amidine substrates are easily synthesized from readily available nitriles. The method is applicable for secondary amide synthesis, based on both aliphatic and (hetero)aromatic amines, including challenging amides consisting of sterically hindered acids and amines. Moreover, the protocol allows one to combine steric bulk with electron deficiency in the target amides (aniline based). Such compounds are difficult to synthesize efficiently based on classical condensation reactions involving carboxylic acids and amines. Overall, the synthetic protocol transforms a nitrile into a secondary amide in both aliphatic and (hetero)aromatic systems.
- Debnath, Pradip,Baeten, Mattijs,Lefvre, Nicolas,Van Daele, Stijn,Maes, Bert U. W.
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supporting information
p. 197 - 209
(2015/03/03)
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- Highly efficient synthesis of amides from ketoximes using trifluoromethanesulphonic anhydride
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Trifluoromethanesulphonic anhydride (triflic anhydride: TA) has been successfully used as a reagent for Beckmann rearrangement in the conversion of a variety of ketoximes into amides without any additive or base. This reagent works well for the synthesis of a library of amides with excellent yields.
- Kalkhambkar, Rajesh G.,Savanur, Hemantkumar M.
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p. 60106 - 60113
(2015/07/27)
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- Iron-Catalyzed C-N Bond Formation via the Beckmann Rearrangement
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A simple, iron-based catalytic system allows for facile Beckmann rearrangement of various oximes. The mild conditions avoid the use of harsh or expensive acids, and the reactions do not require an inert atmosphere. Additionally, a range of amides can be accessed through this transformation.
- Jefferies, Latisha R.,Weber, Savannah R.,Cook, Silas P.
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supporting information
p. 331 - 334
(2015/02/19)
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- Keggin-type Bronsted dodecatungstophosphoric acid: A quasi homogenous and reusable catalyst system for liquid phase Beckmann rearrangement
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A variety of ketoximes, prepared from corresponding ketones, undergo Beckmann rearrangement using H3PW12O40 (DTPA) in acetonitrile under reflux to yield N-substituted amides and lactams in good to excellent yields (72-96%). The present method provides an efficient, clean, eco-friendly, and simple synthesis. The catalyst is cheap, moisture tolerant, recoverable, and reusable without much loss of its activity.
- Kaur, Gagandeep,Rajput, Jaspreet Kaur,Arora, Priya,Devi, Nisha
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p. 1136 - 1140
(2014/02/14)
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- Natural organic acids promoted Beckmann rearrangement: Green and expeditious synthesis of amides under solvent-free conditions
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Naturally occurring organic acids are reported to be highly efficient promoters of the Beckmann rearrangement. Citric, oxalic, tartaric, malic, succinic, malonic, and fumaric acids efficiently promote the Beckmann rearrangement under solvent-free conditions and thermal and microwave irradiation. Tartaric acid was found to be the best promoter of the Beckmann rearrangement under conventional conditions as well as under microwave irradiation. Compared with conventional heating, microwave irradiation provides higher reaction rate and slightly higher yields.
- Rohokale, Sandeep Vasantrao,Kote, Santosh Rajaram,Deshmukh, Santosh Rangnath,Thopate, Shankar Ramchandra
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p. 575 - 578
(2014/01/17)
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- Stannous chloride dihydrate-mediated efficient access to secondary and primary amides from oximes
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Highly selective, efficient and expeditious Beckmann rearrangement of a wide range of ketoximes to secondary amides (20 examples) has been accomplished using stoichiometric amount of stannous chloride dihydrate in the presence of nucleophilic additive, tetra-n-butylammonium iodide (TBAI) (10 moI%) and 4 ? MS in dry acetonitrile at reflux temperature. Aldoximes delivered primary amides through intermediacy of nitriles upon heating with an equimolar amount of SnCl2·2H2O and DBU in dry toluene at reflux in good to acceptable yields (12 examples). Utilization of mild Lewis acid, inexpensive rack reagents and procedural simplicity including easy isolation of products are key advantageous features of the protocol.
- Ganguly, Nemai C.,Nayek, Subhasis,Chandra, Sumanta
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p. 1695 - 1702
(2014/01/17)
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- Synthesis of N-arylamides by copper-catalyzed amination of aryl halides with nitriles
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A copper-catalyzed amination of aryl halides with nitriles has been developed. The use of nitriles as nitrogen nucleophiles can make the synthesis of N-arylamides more simple than that using amides through in-situ hydrolysis. A variety of N-arylamides and benzoxazole derivatives can be synthesized according to this approach. Copyright
- Xiang, Shi-Kai,Zhang, Dong-Xue,Hu, Hao,Shi, Jiang-Ling,Liao, Li-Guo,Feng, Chun,Wang, Bi-Qin,Zhao, Ke-Qing,Hu, Ping,Yang, Hua,Yu, Wen-Hao
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supporting information
p. 1495 - 1499
(2013/06/27)
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- Beckmann rearrangement of ketoximes induced by phenyl dichlorophosphate at ambient temperature
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Upon treatment with phenyl dichlorophosphate (PhOP=OCl2) in acetonitrile at ambient temperature, a variety of ketoximes underwent a Beckmann rearrangement in an effective manner to afford the corresponding amides in moderate to high yields.
- Kuo, Chun-Wei,Hsieh, Min-Tsang,Gao, Shijay,Shao, Yi-Ming,Yao, Ching-Fa,Shia, Kak-Shan
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p. 13662 - 13672
(2013/02/23)
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- Citric acid catalysed Beckmann rearrangement, under solvent free conditions
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Citric acid is reported to be a highly efficient and eco-friendly catalyst for the Beckmann rearrangement under solvent free conditions.
- Thopate, Shankar Ramchandra,Kote, Santosh Rajaram,Rohokale, Sandeep Vasantrao,Thorat, Nitin Madhukar
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experimental part
p. 124 - 125
(2011/07/07)
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- Efficient iodine-mediated beckmann rearrangement of ketoximes to amides under mild neutral conditions
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Aryl ketoximes readily underwent Beckmann rearrangement to give N-substituted amides in excellent yields on electrophilic activation by elemental iodine in anhydrous acetonitrile under reflux. The main advantages of this environmentally friendly protocol include a high selectivity as a result of the absence of any accompanying deprotection to form the parent ketones as byproducts, mild neutral conditions, procedural simplicity, and particularly ease of isolation of the products.
- Ganguly, Nemai C.,Mondal, Pallab
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experimental part
p. 3705 - 3709
(2011/01/03)
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- Novel thienopyrrole glycogen phosphorylase inhibitors: Synthesis, in vitro SAR and crystallographic studies
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Two series of novel thienopyrrole inhibitors of recombinant human liver glycogen phosphorylase a (GPa) which are effective in reducing glucose output from rat hepatocytes are described. Representative compounds have been shown to bind at the dimer interface site of the rabbit muscle enzyme by X-ray crystallography.
- Whittamore, Paul R.O.,Addie, Matthew S.,Bennett, Stuart N.L.,Birch, Alan M.,Butters, Michael,Godfrey, Linda,Kenny, Peter W.,Morley, Andrew D.,Murray, Paul M.,Oikonomakos, Nikos G.,Otterbein, Ludovic R.,Pannifer, Andrew D.,Parker, Jeremy S.,Readman, Kristy,Siedlecki, Pawel S.,Schofield, Paul,Stocker, Andy,Taylor, Melvyn J.,Townsend, Linda A.,Whalley, David P.,Whitehouse, Jennifer
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p. 5567 - 5571
(2007/10/03)
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- [Yb(OTf)3] catalysed facile conversion of ketoximes to amides and lactams
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A variety of ketoximes undergo the Beckmann rearrangement upon a treatment with a catalytic amount of [Yb(OTf)3] in refluxing acetonitrile to afford the corresponding amides and lactams in excellent yields with high selectivity.
- Yadav,Reddy,Madhavi,Ganesh
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p. 236 - 238
(2007/10/03)
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- The first synthesis of N-alkyl-N-arylthiocarbamoylacetates and acetic acids
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N-Alkyl-N-arylthiocarbamoylacetates, the key intermediates for the synthesis of novel antinephritic agents, have been prepared for the first time. Some of the esters were in turn hydrolyzed to the corresponding acids. An alternative, indirect synthetic route was also developed to prepare some unusual acids.
- Spears, Glen W.,Tsuji, Kiyoshi,Tojo, Takashi,Nishimura, Hiroaki,Ogino, Takashi
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p. 565 - 574
(2007/10/03)
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- The synthesis of highly active thiophene ring-containing chromophore components for photonic polymers based on a newly designed route
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2-Aminothiophene derivatives are the key intermediates for the present synthesis. It is known that the synthesis of 2-aminothiophene is troublesome although it is a rather simple heterocycle. In this work, an early report was newly developed as a basis for the efficient synthesis of thiophene-ring-containing chromophore components for photonic polymers. 2-Amino-5-nitrothiophene and 2-amino-3,5-dinitrothiophene were synthesized in excellent yield. After diazotization, the 2-aminothiophene derivatives were directly treated with N-phenyldiethanolamine to afford two-electron push-pull compounds. A similar styryl compound was also prepared. All of these chromophore molecules have further polymerizable hydroxy groups on one end of the molecule. These compounds are currently showing interesting potential in making highly sensitive, nonlinear optical polymeric materials. The Royal Society of Chemistry 1999.
- Yuquan, Shen,Yuxia, Zhao,Zao, Li,Jianghong, Wang,Ling, Qiu,Shixiong, Liu,Jianfeng, Zhai,Jiayun, Zhou
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p. 3691 - 3695
(2007/10/03)
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- N-(5-Substituted) thiophene-2-alkylsulfonamides as potent inhibitors of 5-lipoxygenase
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Compound 4k N-[5-(4-fluoro)phenoxythien-2-yl]methanesulfonamide is representative of a new class of potent inhibitors of 5-lipoxygenase (5-LO). These versatile compounds exhibit dose-dependent inhibition of 5-LO with IC50s ranging from 20-100 nM in the rat basophilic leukemia (RBL-1) cell homogenate assay and submicromolar IC50s in both the RBL-1 and human peripheral blood leukocyte (PBL) whole cell assays. Compound 4k also showed significant anti-inflammatory activity in the adjuvant arthritic rat at an oral dose of 3 mg/kg.
- Beers, Scott A.,Malloy, Elizabeth A.,Wu, Wei,Wachter, Michael,Ansell, Justin,Singer, Monica,Steber, Michele,Barbone, Arminda,Kirchner, Thomas,Ritchie, David,Argentieri, Dennis
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p. 779 - 786
(2007/10/03)
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- REDUCTIVE ACYLATION OF 5-NITRO-2R-THIOPHENES
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A study was made of the kinetics of the reduction of eleven 5-nitro-2-substituted thiophenes to acetylaminothiophenes using Raney nickel in acetic anhydride.The dependence of the rate of the reaction both on the induction effect of the substituents and on the ratio of the adsorption constants of the reaction products and substrate was determined.
- Glushkova, A. A.,Morgunova, L. M.,Freidlin, G. N.,Fedorov, A. Ya.,Ivanov, V. F.
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p. 380 - 384
(2007/10/02)
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- BECKMANN REARRANGEMENT OF ACETYLTHIOPHENE OXIME BENZENESULFONATES AS A METHOD FOR THE SYNTHESIS OF ACETAMIDOTHIOPHENES
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The Beckmann rearrangement of 2-acetylthiophene, 5-methyl-2-acetylthiophene, 5-chloro-2-acetylthiophene, and 2,5-dichloro-3-acetylthiphene oxime benzenesulfonates to the corresponding acetamidothiophenes was carried out by heating with an aqueous methanol solution of sodium acetate.This method can be used for the preparative synthesis of 2-acetamidothiophene and 2,5-dichloro-3-acetamidothiophene.
- Fabrichnyi, B. P.,Bulgakova, V. N.,Gol'dfarb, Ya. L.
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p. 401 - 403
(2007/10/02)
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- E- and Z-Isomerism of 2-Acetylthiophene Oximes
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A study of the oximation of a number of 2-acetylthiophenes in order to ascertain the validity of contradictory results previously described is reported.The fact that the steric hidrance is smaller in 2-acetylthiophenes unsubstituted at position-3 than in acetylbenzenes allows in these cases the formation of Z-oximes, which even can predominate on the E oximes in the case of a +M substitution at position-5.In the paper is also shown that the E/Z ratio of 2-acetylthiophene oximes can be deduced from 1H-nmr spectrum of the crude reaction mixture.
- Conde, Santiago,Corral, Carlos,Lissavetzky, Jaime
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p. 301 - 304
(2007/10/02)
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- 5-(N-Alkyl-N-acyl-amino)-thiophen-2-carboxylic acid derivatives
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The present invention refers to new 5-(N-Alkyl-N-acyl-amino)-thiophen-2-carboxylic acid derivatives having the general formula I STR1
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- Process for manufacturing heterocyclic compounds
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A process for the manufacture of the heterocyclic compounds of the formula: SPC1 Wherein R is a hydrogen atom or a hydrocarbon radical, which comprises decarboxylating and dinitrating a compound of the formula: SPC2 Wherein R has the meaning stated above, and finally hydrolysing off the acyl group, and the use of the said heterocyclic compounds as diazo components in the production of azo dyestuffs.
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