- Preparation method of 4', 6-diamidinyl-2-phenylindole dihydrochloride
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The invention discloses a preparation method of 4', 6-diamidinyl-2-phenylindole dihydrochloride, which comprises the following steps: firstly, taking 6-substituted indole as a raw material, and reacting with formamide under the action of a reaction solvent and a first catalyst to prepare 6-cyano indole; then performing a reactionthe 6-cyanoindole and the 4-substituted cyanobenzene under the action of a second catalyst, and obtaining 6-cyano-2-(4 '-cyanophenyl) indole; using 6-cyano-2-(4'-cyanophenyl) indole as a raw material and reacting with alcohol containing a substituent group under the action of a third catalyst, and obtaining 4', 6-bis (substituent group-containing methyleneimic acid ester)-2-phenylindole dihydrochloride; finally, continuously reacting with ammonium chloride, and obtaining the 4', 6-diamidinyl-2-phenylindole dihydrochloride. The design route is reasonable in design, the process safety is high, the method is friendly to operators, the cost is low, and the requirement for industrial production of products can be fully met.
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Paragraph 0028-0031; 0041-0044; 0056-0059
(2021/06/26)
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- Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species
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Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.
- Dong, Yanan,Li, Yuehui,Yang, Peiju,Zhao, Shizhen
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- A carboxamide is the cyanogen source of aromatic nitrile to the preparation method of the (by machine translation)
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The invention discloses a method for preparing aromatic nitrile, is under the action of the nickel catalyst, in order to carboxamide is the cyanogen source, and with various substituents haloarene coupled reactions, preparing aromatic nitrile. The reaction temperature is 100 - 160 °C, the reaction time is 6 - 24 hours. It overcomes the traditional aromatic nitrile of the synthesis method operation of complex steps, requires the use of a toxic, more expensive, functionalization of the cyanogen source as the reaction raw material and the like. Compared with the traditional method, this method is simple to use cheap, green non-toxic of the formamide is cyano sources; without the need of external dehydrating agent, formamide in the nickel catalyst of the catalytic dehydration at the same time, with a nickel catalyst in coordination with the halogenated aromatic hydrocyanation, more economic, high-efficiency, environmental protection; at the same time the method exhibits good substrate universality, to air, moisture, light are not sensitive, high yield, product separation and purification is simple, with wide application. (by machine translation)
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Paragraph 0015; 0016; 0017; 0018-0024; 0116; 0117-0121
(2019/05/08)
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- Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions
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The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.
- Yang, Luo,Liu, Yu-Ting,Park, Yoonsu,Park, Sung-Woo,Chang, Sukbok
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p. 3360 - 3365
(2019/03/26)
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- A room temperature cyanation of (hetero)aromatic chlorides by an air stable nickel(II) XantPhos precatalyst and Zn(CN)2
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A methodology for the synthesis of (hetero)aromatic nitriles from aryl chlorides at room temperature has been developed. This methodology uses an air and moisture stable nickel(ii) XantPhos precatalyst and Zn(CN)2 as the cyanide (CN-) source.
- Beattie, D. Dawson,Schareina, Thomas,Beller, Matthias
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supporting information
p. 4291 - 4294
(2017/07/10)
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- A Homogeneous Method for the Conveniently Scalable Palladium- and Nickel-Catalyzed Cyanation of Aryl Halides
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Homogeneous conditions for the palladium-catalyzed cyanation of aryl halides were developed. This new system features a broad scope of aryl chlorides and bromides, uses 2-propanol or 1-butanol as solvent, and is readily scalable. The same conditions can also provide simple benzonitriles using the recently developed (TMEDA)NiCl(o-tolyl) precatalyst in conjunction with 1,1′-bis(diphenylphosphino)ferrocene (dppf) as a ligand.
- Burg, Finn,Egger, Julian,Deutsch, Johannes,Guimond, Nicolas
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p. 1540 - 1545
(2016/08/30)
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- Indolyne experimental and computational studies: Synthetic applications and origins of selectivities of nucleophilic additions
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Efficient syntheses of 4,5-, 5,6-, and 6,7-indolyne precursors beginning from commercially available hydroxyindole derivatives are reported. The synthetic routes are versatile and allow access to indolyne precursors that remain unsubstituted on the pyrrole ring. Indolynes can be generated under mild fluoride-mediated conditions, trapped by a variety of nucleophilic reagents, and used to access a number of novel substituted indoles. Nucleophilic addition reactions to indolynes proceed with varying degrees of regioselectivity; distortion energies control regioselectivity and provide a simple model to predict the regioselectivity in the nucleophilic additions to indolynes and other unsymmetrical arynes. This model has led to the design of a substituted 4,5-indolyne that exhibits enhanced nucleophilic regioselectivity.
- Im, G-Yoon J.,Bronner, Sarah M.,Goetz, Adam E.,Paton, Robert S.,Cheong, Paul H.-Y.,Houk,Garg, Neil K.
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supporting information; experimental part
p. 17933 - 17944
(2011/02/26)
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- COMPOUNDS
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The present invention relates to novel oxadiazole derivatives having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders.
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Page/Page column 18
(2010/03/02)
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- Synthesis, DNA binding, fluorescence measurements and antiparasitic activity of DAPI related diamidines
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A novel series of extended DAPI analogues were prepared by insertion of either a carbon-carbon triple bond (16a-d) or a phenyl group (21a,b and 24) at position-2. The new amidines were evaluated in vitro against both Trypanosoma brucei rhodesiense (T. b. r.) and Plasmodium falciparum (P. f.). Five compounds (16a, 16b, 16d, 21a, 21b) exhibited IC50 values against T. b. r. of 9 nM or less which is two to nine folds more effective than DAPI. The same five compounds exhibited IC50 values against P. f. of 5.9 nM or less which is comparable to that of DAPI. The fluorescence properties of these new molecules were recorded, however; they do not offer any advantage over those of DAPI.
- Farahat, Abdelbasset A.,Kumar, Arvind,Say, Martial,Barghash, Alaa El-Din M.,Goda, Fatma E.,Eisa, Hassan M.,Wenzler, Tanja,Brun, Reto,Liu, Yang,Mickelson, Leah,Wilson, W. David,Boykin, David W.
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scheme or table
p. 557 - 566
(2010/04/29)
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- COMPOUNDS
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The present invention relates to novel oxadiazole derivatives having pharmacological activity, processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of various disorders.
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Page/Page column 38
(2010/01/12)
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- Phenylpiperazine derivatives with a combination of partial dopamine-D2 receptor agonism and serotonin reuptake inhibition
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The invention relates to a group of novel phenylpiperazine derivatives with a dual mode of action: serotonin reuptake inhibition and partial agonism on dopamine-D2 receptors. The invention also relates to the use of a compound disclosed herein for the manufacture of a medicament giving a beneficial effect. The compounds have the general formula (1): wherein the symbols have the meanings given in the specification. and tautomers, stereoisomers and N-oxides thereof, as well as pharmacologically acceptable salts, hydrates and solvates of said compounds of formula (1) and its tautomers, stereoisomers and N-oxides.
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Page/Page column 20
(2010/11/08)
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- Total synthesis of stephanotic acid methyl ester
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The methyl ester of the naturally occurring macrocyclic pentapeptide stephanotic acid, containing an unusual β-substituted α-amino acid with a tryptophan C-6 to leucine β-carbon link, has been synthesized. The key steps include the formation of this amino acid through a thioxo-oxazolidine intermediate and a Horner-Wadsworth-Emmons reaction using a phosphonoglycine, derived by a dirhodium(II)-catalyzed N-H insertion reaction, to give a dehydroamino acid and subsequent rhodium(I)-catalyzed asymmetric hydrogenation to introduce the modified tryptophan residue.
- Bentley, David J.,Slawin, Alexandra M. Z.,Moody, Christopher J.
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p. 1975 - 1978
(2007/10/03)
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- Some Observations on the Formation of 1-Hydroxyindoles in the Leimgruber-Batcho Indole Synthesis
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The factors influencing the formation of 1-hydroxyindoles in the catalytic hydrogenation of β-dimethylamino-2-nitrostyrenes (Leimgruber-Batcho indole synthesis) have been investigated.Significant amounts of 1-hydroxyindoles were obtained only when the β-dimethylamino-2-nitrostyrene was substituted with an electron-withdrawing group at the 5 or 6 position.The proportion of 1-hydroxyindole formed relative to the normal indole product was found to increase as both the amount of catalyst and hydrogen pressure were decreased.
- Clark, Robin D.,Repke, David B.
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p. 121 - 125
(2007/10/02)
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- Intermediates for indoles
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Ortho-nitrotoluenes are condensed with formamide acetals to yield the corresponding otho-nitro-β-aminestyrenes which undergo cyclization upon reduction to yield indoles.
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