- 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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- Palladium Catalyzed Direct Acylation of Iodo-Acetanilides/Iodo-Phenyl Acetates: Domino One-Pot Synthesis of 2-Quinolinones
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Pd-catalyzed direct acylation reaction of iodoacetanilides/iodophenyl acetates with aldehydes is presented. Simple, bench-top aldehydes were used as non-toxic acylating agents. This protocol comprises direct coupling with aldehydes without activating the carbonyl group and without directing group assistance. The strategy was applied to a domino one-pot synthesis of 2-quinolinones through acylation and intramolecular aldol condensation. Significantly, the strategy was extended to the domino one-pot synthesis of drugs and bioactive compounds.
- Basuli, Scuhand,Satyanarayana, Gedu
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p. 957 - 970
(2017/12/07)
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- Visible-Light-Induced Decarboxylation Coupling/Intramolecular Cyclization: A One-Pot Synthesis for 4-Aryl-2-quinolinone Derivatives
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A visible-light-induced decarboxylation coupling/intramolecular cyclization is reported. The one-pot synthesis system provides mild, efficient, and atom economical access to the synthesis of 4-aryl-2-quinolinone derivatives. It is notable that the necessa
- Wang, Chenglong,Qiao, Jingyi,Liu, Xiaochong,Song, He,Sun, Zhizhong,Chu, Wenyi
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p. 1422 - 1430
(2018/02/09)
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- Selectfluor-mediated mono-C–H activation: The syntheses of mono-ortho-substituted anilides
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The C–H activation of aryl amide using readily available Pd(OAc)2 in the presence of selectfluor is reported. The highly mono-selective introduction of sp2 hybridized functional groups have been realized. A broad range of aryl-, alke
- Zhu, Ranran,Lu, Shaonan,Wang, Qing,Bai, Jinshan,Wang, Yuntao,Yu, Qingzhen,Huang, Jianhui
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p. 3879 - 3887
(2018/06/15)
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- 4-Phenyl quinoline derivatives as potential serotonin receptor ligands with antiproliferative activity
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Antagonists of signaling receptors are often effective non-toxic therapeutic agents. Over the years, there have been evidences describing the role of serotonin or 5-hydroxytryptamine (5-HT) in development of cancer. Although there are reports on the antip
- Joshi, Pranaya V.,Sayed, Alim A.,RaviKumar, Ameeta,Puranik, Vedavati G.,Zinjarde, Smita S.
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p. 246 - 258
(2017/05/12)
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- Merging Photoredox with Palladium Catalysis: Decarboxylative ortho-Acylation of Acetanilides with α-Oxocarboxylic Acids under Mild Reaction Conditions
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A room temperature decarboxylative ortho-acylation of acetanilides with α-oxocarboxylic acids has been developed via a novel Eosin Y with Pd dual catalytic system. This dual catalytic reaction shows a broad substrate scope and good functional group tolera
- Zhou, Chao,Li, Pinhua,Zhu, Xianjin,Wang, Lei
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supporting information
p. 6198 - 6201
(2016/01/09)
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- Metal-free synthesis of 1H-indole-2-carbaldehydes by N-iodosuccinimide- mediated cyclization of 1-(2′-anilinyl)prop-2-yn-1-ols in water. A formal synthesis of (R)-calindol
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A N-iodosuccinimide (NIS)-mediated method to prepare 1H-indole-2- carbaldehydes efficiently from cycloisomerization of 1-(2-aminophenyl)prop-2-yn- 1-ols is described. The reaction is operationally straightforward and accomplished in good to excellent yiel
- Kothandaraman, Prasath,Lauw, Sherman Jun Liang,Chan, Philip Wai Hong
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p. 7471 - 7480
(2013/08/23)
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- Palladium-catalyzed direct oxidative ortho-acylation of anilides with toluene derivatives
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Direct oxidative ortho-acylation reaction of anilides with toluene derivatives in the presence of palladium acetate using tert-butyl hydroperoxide as an oxidant was developed. A broad range of diaryl ketones was obtained in good to excellent yields (up to 95%). The plausible mechanism was also proposed.
- Weng, Jianquan,Yu, Zhiqin,Liu, Xinghai,Zhang, Guofu
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supporting information
p. 1205 - 1207
(2013/03/13)
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- Palladium-catalyzed direct ortho -acylation through an oxidative coupling of acetanilides with toluene derivatives
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A facile ortho-acylation of acetanilides by a Pd-catalyzed oxidative C-H activation was developed in which low toxic, stable, and commercially available toluene derivatives were first used as acylation reagents by a tandem reaction to form o-acylacetanili
- Yin, Zhangwei,Sun, Peipei
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p. 11339 - 11344
(2013/02/23)
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- Dihydroquinazolines as a novel class of Trypanosoma brucei trypanothione reductase inhibitors: Discovery, synthesis, and characterization of their binding mode by protein crystallography
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Trypanothione reductase (TryR) is a genetically validated drug target in the parasite Trypanosoma brucei, the causative agent of human African trypanosomiasis. Here we report the discovery, synthesis, and development of a novel series of TryR inhibitors based on a 3,4-dihydroquinazoline scaffold. In addition, a high resolution crystal structure of TryR, alone and in complex with substrates and inhibitors from this series, is presented. This represents the first report of a high resolution complex between a noncovalent ligand and this enzyme. Structural studies revealed that upon ligand binding the enzyme undergoes a conformational change to create a new subpocket which is occupied by an aryl group on the ligand. Therefore, the inhibitor, in effect, creates its own small binding pocket within the otherwise large, solvent exposed active site. The TryR-ligand structure was subsequently used to guide the synthesis of inhibitors, including analogues that challenged the induced subpocket. This resulted in the development of inhibitors with improved potency against both TryR and T. brucei parasites in a whole cell assay.
- Patterson, Stephen,Alphey, Magnus S.,Jones, Deuan C.,Shanks, Emma J.,Street, Ian P.,Frearson, Julie A.,Wyatt, Paul G.,Gilbert, Ian H.,Fairlamb, Alan H.
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experimental part
p. 6514 - 6530
(2011/12/02)
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- Palladium-catalyzed oxidative C-H bond acylation of acetanilides with benzylic alcohols
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An efficient and clean method to construct C-C bonds has been developed via the acylation reaction of acetanilides with benzylic alcohols using tert-butyl hydroperoxide (TBHP) as oxidant catalyzed by palladium acetate in the presence of triflic acid (TfOH). The acylation reactions exhibit excellent reactivities, and up to 95% yield of the corresponding aryl ketone could be obtained under the optimal conditions. Copyright
- Yuan, Yu,Chen, Duanteng,Wang, Xiaowei
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supporting information; experimental part
p. 3373 - 3379
(2012/02/03)
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- Asymmetric synthesis of 1,3-diamines by diastereoselective reduction of enantiopure n-tert-butanesulfinylketimines: unusual directing effects of the ortho-substituent
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(Figure Presented) Chiral, nonracemic 1,3-diamines were prepared in a highly diastereoselective reduction of diaryl N-tert-butanesulfinylketimines. Correlation between facial selectivity of the reduction and E or Z geometry of the starting ketimines suggests involvement of a cyclic transition state for the reduction. The ortho-substituent controls the geometry of N-tert- butanesulfinylketimines in the solid state and provides additional stabilization of the cyclic transition state.
- Martjuga, Marina,Shabashov, Dmitry,Belyakov, Sergey,Liepinsh, Edvards,Suna, Edgars
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supporting information; experimental part
p. 2357 - 2368
(2010/07/02)
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- N,N'-Diiodo-N,N'-1,2-ethanediylbis(p-toluenesulfonamide) as an efficient catalyst for acetylation of alcohols, phenols, amines, and thiols under solvent-free conditions
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N,N'-Diiodo-N,N'-1,2-ethanediylbis(p-toluenesulfonamide) (NIBTS) is a highly efficient catalyst for the acetylation of alcohols, phenols, amines, and thiols under solvent-free conditions. Primary, secondary, tertiary alcohols; phenols; amines; and thiols can be easily acetylated in good to excellent yields at 80 C. Copyright Taylor & Francis Group, LLC.
- Ghorbani-Vaghei, Ramin,Toghraei-Semiromi, Zahra
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experimental part
p. 1701 - 1707
(2010/09/17)
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- Micellar Catalysis of Organic Reactions. XXX A Study of the Mechanism of Hydrolysis of Oxazepam and 2'-Methyldiazepam in the Presence of Micelles and in Water
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Acidic hydrolysis of oxazepam in water involved initial azomethine cleavage at low acid concentrations (0.1-0.2 M) with initial amide hydrolysis occurring concurrently at higher acid concentrations (0.3-0.6 M).In the presence of micelles of sodium dodecyl sulfate the percentage of initial amide cleavage increased.For the basic hydrolysis of oxazepam in water the rate was dependent on indicating at least some initial amide hydrolysis.At higher base concentrations the rate became independent of , because of the ionization of the NH group of oxazepam, producing an unreactive nitranion.In the presence of cetyltrimethylammonium bromide, the rate of basic hydrolysis was slower than in water, due to the increased amount of ionization in the presence of micelles.Acidic hydrolysis of 2'-methyldiazepam in water was independent of in the range 0.1-0.3 M, indicating initial azomethine hydrolysis.The rate was slower than for diazepam itself, indicating the existence of steric hindrance by the 2'-methyl group to water attack at C5.In basic solution, a biphasic reaction was observed.The rate of the first phase was dependent on , indicating the presence of initial amide hydrolysis for 2'-methyldiazepam, cf. initial azomethine hydrolysis for diazepam.At high base concentrations, a greater than first-order dependence on base concentration was observed.This was attributed to the formation of dianionic intermediates, as previously reported for the hydrolysis of similar anilides at high base concentrations.
- Broxton, Trevor J.,Wright, Sallyanne
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p. 103 - 111
(2007/10/02)
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- Reinvestigation of a 5H-Dibenzotriazonine Synthesis
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Treatment of 5-chloro-2-aminobenzophenone (1) with o-phenylenediamine, sodium acetate, and acetic acid gave 2-(acetyl)amino-5-chlorobenzophenone (5) rather than N--1,2-benzenediamine (3), as reported by Kulkarni et al.Authentic 3 was prepared and treated with chloroacetic acid and polyphosphoric acid (PPA) to give 1, recovered 3, 2,8-dichloro-6,12-diphenyldibenzodiazocine (9) and 2-chloro-6-(chloromethyl)-13-phenyl-5H-dibenzotriazonine (10).Treatment of 5 with PPA, with or without chloroacetic acid, gave phenyl> phenylmethanone (11) as the sole product in 90percent yield.Treatment of other benzophenones, acetophenones, and anilines with sodium acetate and acetic acid provided acetanilides in 78-96percent yield, with the exception of 2'-aminoacetophenone (20), wich gave a quantitative yield of 2--4-methylquinoline (21).The mechanism of acetanilide formation with sodium acetate and acetic acid is discussed.The structure of 21 was established using high resolution 1H nmr techniques.Attempts to prepare an authentic sample of 21 from 2-chlorolepidine (26) and (20) gave 4-methyl-N--2-quinolinamine (29) as the major product.
- Peet, Norton P.,Sunder, Shyam,Barbuch, Robert J.,Whalon, Michael R.,Huber, Edward W.,Huffman, John C.
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p. 1611 - 1618
(2007/10/02)
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- 2-[3-(Phthalimidomethyl)-5-methyl-4H-1,2,4-triazol-4-yl]benzophenones
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A process to make 6-phenyl-4H-s-triazolo[4,3-a][1,4]-benzodiazepines by converting 2-[3-(hydroxymethyl)-4H-1,2,4-triazol-4-yl]benzophenones to 2-[3-[(phthalimido or methanesulfonyl)methyl]-4H-1,2,4-triazol-4-yl]benzophenones and converting these compounds to the highly active 6-phenyl-4H-s-triazolo[4,3-a][1,4]benzodiazepines useful as tranquilizers and sedatives.
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- Triazolyl benzophenone compounds
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Intermediates of the formula IV: STR1 wherein R is selected from the group consisting of hydrogen and alkyl of 1 to 3 carbon atoms, inclusive; and wherein R2, R3, and R4 are selected from the group consisting of hydrogen, fluoro, chloro, bromo, nitro, and trifluoromethyl are produced by a multistep synthesis. The final compounds are tranquilizers and sedatives and can be used in mammals, including man, and in birds.
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