- Safe and efficient reductive methylation of primary and secondary amines using N-methylpyrrolidine zinc borohydride
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An efficient, general procedure for reductive methylation of primary and secondary amines with 37% formaldehyde using N-methylpyrrolidine zinc borohydride (ZBHNMP) as a reducing agent gave the corresponding tertiary amines in excellent yields. The reaction was carried out in tetrahydrofuran under neutral conditions at 0-10°C. Copyright Taylor & Francis Group, LLC.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Salehian, Fatemeh,Fazli, Kazem
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- Photochemical Reaction of N,N-Dimethylanilines with N-Substituted Maleimides Utilizing Benzaldehyde as the Photoinitiator
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Photoorganocatalysis constitutes a powerful domain of photochemistry and organic synthesis. The scaffold of pyrrolo[3,4-c]quinolinoles exhibits interesting and potent inhibition against various enzymes, making them really promising pharmaceutical targets. Herein, we describe a photochemical methodology for the reaction of N,N-dimethylanilines with N-substituted maleimides, utilizing benzaldehyde as the photoinitiator. A variety of substituted N,N-dimethylanilines and N-substituted maleimides were converted into the corresponding adducts in moderate to high yields.
- Nikitas, Nikolaos F.,Theodoropoulou, Maria A.,Kokotos, Christoforos G.
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- Deoxygenation of Tertiary Amine Oxides with Carbon Disulfide
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Reduction of various tertiary amine oxides with carbon disulfide was examined and kinetic experiments were carried out.Trialkylamine oxides and N,N-dialkylarylamine N-oxides were readily reduced by CS2 to give the corresponding tertiary amines in good yields, while heteroaromatic amine N-oxides such as picoline N-oxide were not affected.The oxygen atom in the N-oxide was found to be transferred to CO2 upon mass spectral analysis of the gas evolved.The kinetic experiments were carried out following the UV spectra of N,N-dimethylaniline N-oxide in CH3CN containing much excess of CS2 and the rate was found to be of 2nd order in the N-oxide and CS2.Activation parameters (ΔH=55.7 kJ mol-1, ΔS=-78.2 J K-1 mol-1 at 20 deg C) are characteristic of a normal bimolecular reaction.The logarithms of the rate constants for para-substituted N,N-dimethylaniline N-oxides are nicely correlated with Hammett ? values and a small negative ρ value (ρ=-0.2) was obtained.The rate of reaction was faster in polar aprotic solvents than in nonpolar or protic solvents.These observations seem to suggest that the reaction proceeds via an initial nucleophilic attack of the N-oxide oxygen at carbon disulfide followed by the rate-determining N-O bond fission to give the tertiary amine.
- Yoshimura, Toshiaki,Asada, Kaoru,Oae, Shigeru
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- Demonstrating the Synergy of Synthetic, Mechanistic, and Computational Studies in A Regioselective Aniline Synthesis
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Tri- and tetrasubstituted anilines are formed in good to excellent yields by the addition of ketones to vinamidinium salts (up to 98%). The reaction proceeds via the formation of dienone intermediates, which react to form an enamine with the liberated amine. In the case of a nitro, or dimethylaminomethylene substituent, the enamines undergo a facile electrocyclic ring closure to form a cyclohexadiene, which goes on to form anilines with a high degree of selectivity (up to 50:1) with a minor competing pathway proceeding via the enol providing phenols. Competition experiments using isotopic substitution reveal that the rate determining step en route to dienone is enol/enolate addition to the vinamidinium salt, which is characterized by an inverse secondary isotope effect (kH/D 0.7-0.9). Computational studies have been used to provide a framework for understanding the reaction pathway. The original proposal for a [1,5]-H shift was ruled out on the basis of the calculations, which did not locate a thermally accessible transition state. The minimum energy conformation of the enamine is such that a facile electrocyclic ring closure is ensured, which is corroborated by the experimental studies. A framework for understanding the reaction pathway is presented.
- Davies, Ian W.,Marcoux, Jean-Francois,Kuethe, Jeffery T.,Lankshear, Michael D.,Taylor, Jeremy D. O.,Tsou, Nancy,Dormer, Peter G.,Hughes, David L.,Houk,Guner, Vildan
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- Selective utilization of methoxy groups in lignin for: N -methylation reaction of anilines
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The utilization of lignin as a feedstock to produce valuable chemicals is of great importance. However, it is a great challenge to produce pure chemicals because of the complex structure of lignin. The selective utilization of specific groups on lignin molecules offers the possibility of preparing chemicals with high selectivity, but this strategy has not attracted attention. In this work, we propose a protocol to produce methyl-substituted amines by the selective reaction of the methoxy groups of lignin and aniline compounds. It was found that LiI in the ionic liquid 1-hexyl-3-methylimidazolium tetrafluoroborate could catalyze the reaction efficiently and the selectivity to the N-methylation product could be as high as 98%. Moreover, the lignin was not depolymerized in the reaction. As it was rich in hydroxyl groups, the residual material left over after the reaction was used as an efficient co-catalyst for the cycloaddition of epoxy propane with CO2, using KI as the catalyst.
- Mei, Qingqing,Shen, Xiaojun,Liu, Huizhen,Liu, Hangyu,Xiang, Junfeng,Han, Buxing
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- Iron-catalyzed aryl-aryl cross coupling route for the synthesis of 1-(2-amino)-phenyl)dibenzo[b,d]furan-2-ol derivatives and their biological evaluation
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Naturally occurring dibenzofuran motifs represent promising lead structures for the development of novel antimycobacterial agents. Prompted by our recent development of cross dehydrogenative coupling using iron catalysis, we extended our strategy to synthesize 14 novel anilinodibenzofuranols and they were explored for anti-tubercular and cytotoxic activities. Consistent with our hypothesis, DBF-3, 14 and 16 exhibited promising activity against two strains (M. tuberculosis H37Rv and the clinical S, H, R, and E resistant isolate), while DBF-13, 18 exhibited selective inhibitory activity only against the clinical S, H, R and E resistant isolate. However, the compounds DBF-4 and DBF-8 showed promising and selective antitumor activity against the tested cancer cell lines. The Royal Society of Chemistry 2013.
- Chiranjeevi, Barreddi,Koyyada, Ganesh,Prabusreenivasan,Kumar, Vanaja,Sujitha, Pombala,Kumar, C. Ganesh,Sridhar,Shaik, Saida,Chandrasekharam, Malapaka
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- A quantitative assessment of the production of OH and additional oxidants in the dark Fenton reaction: Fenton degradation of aromatic amines
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This paper reports the results of a kinetic study into the transformation of 2,4- and 3,4-dichloroaniline (2,4-DCA, 3,4-DCA) and of methyl yellow (MY) with the Fenton reagent in aqueous solution. All the substrates can be degraded in the presence of Fe(II) + H2O2, but the reaction between Fe(II) and H2O2 causes substrate degradation and Fe(II) oxidation within seconds under the adopted conditions. The HPLC, GC-MS and IC analyses only allow the monitoring of the reaction after all Fe(II) has been consumed, when degradation proceeds more slowly via Fe(III) reduction to Fe(II). Substrate degradation in the first part of the reaction was studied by stopped-flow spectrophotometry, using MY as substrate. The results are consistent with a reaction involving OH, where both Fe(II) and H 2O2 compete with MY for the hydroxyl radical. However, the experimental data indicate that OH is unlikely to be the only product of the reaction between Fe(II) and H2O2. Another species, possibly the ferryl ion (FeO2+), is formed as well but has a negligible role in MY degradation. The Fenton reaction would thus yield both OH (about 60% at pH 2) and ferryl (about 40%), and the 60:40 branching ratio between OH and the other species is compatible with additional data here reported concerning the degradation of 2,4-DCA and 3,4-DCA in the first ferrous step of the Fenton reaction. The reported findings will hopefully indicate a way out of a long-lasting controversy concerning the mechanism of the Fenton process, also suggesting an approach to quantitatively determine the formation yields of the reactive species as well as a strategy to identify the reactant that is actually involved in substrate transformation.
- Minero, Claudio,Lucchiari, Mirco,Maurino, Valter,Vione, Davide
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- Traceless Directing-Group Strategy in the Ru-Catalyzed, Formal [3 + 3] Annulation of Anilines with Allyl Alcohols: A One-Pot, Domino Approach for the Synthesis of Quinolines
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A unique, ruthenium-catalyzed, [3 + 3] annulation of anilines with allyl alcohols in the synthesis of substituted quinolines is reported. The method employs a traceless directing group strategy in the proximal C-H bond activation and represents a one-pot Domino synthesis of quinolines from anilines.
- Kumar, Gangam Srikanth,Kumar, Pravin,Kapur, Manmohan
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- Air-tolerant direct reductive N-methylation of amines using formic acid via simple inorganic base catalysis
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The construction of N-methyl amine moieties is an important reaction that has found numerous applications. Development of new methylation agents that are more environmentally benign than classical agents, such as iodomethane and methyl sulfate, is still highly desirable. Herein, we report a convenient protocol for direct reductive N-methylation of amines using formic acid as the methylation agent via simple inorganic base catalysis. The present protocol operates under transition-metal-free and air-tolerant conditions. Both the catalyst, K2HPO4, and the reductant, polymethylhydrosiloxane (PMHS), are cheap and easily separable from the crude reaction product mixture. Mechanistic investigations suggest that the reaction occur through the formation of an acetal intermediate followed by the C–N bond formation.
- Huang, Yan,Deng, Wei,Lin, Bo-Lin
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- 1,4-Dioxane-Tuned Catalyst-Free Methylation of Amines by CO2 and NaBH4
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A catalyst-free reductive functionalization of CO2 with amines and NaBH4 was developed. The N-methylation of amines was carried out with CO2 as a C1 building block and 1,4-dioxane as the solvent. Notably, the six-electron reduction of CO2 to form the methyl group occurred simultaneously with formation of the C?N bond to give the N-methylated amine.
- Guo, Zhiqiang,Zhang, Bo,Wei, Xuehong,Xi, Chanjuan
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- N-methylation of aromatic amines and N-heterocycles under acidic conditions with the TTT (1,3,5-trioxane-triethylsilane-trifluoroacetic acid) system
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A novel reductive N-methylation protocol under acidic conditions with the TTT (1,3,5-trioxane-triethylsilane-trifluoroacetic acid) system is disclosed. This method is highly specific for aromatic amines and several N-heterocycles (indoles and annulated analogues, phenoxazine, phenothiazine), insensitive to steric hindrance, and compatible with a wide range of functional groups. Further the N-methylation step can be combined with an in situ N-Boc deprotection. Compounds in which the nucleophilicity of the NH group is eliminated by protonation under the reaction conditions (aliphatic amines, azaarenes of noteworthy basicity) are inert. In several examples, it was demonstrated that the TTT system is complementary to other N-methylation protocols.
- Popp, Tobias A.,Bracher, Franz
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- Selenium-catalyzed carbonylation of nitroarenes to symmetrical 1,3-diarylureas under atmospheric pressure
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Selenium-catalyzed carbonylation of nitrobenzene and substituted nitroarenes with CO under atmospheric pressure afforded symmetrical 1,3-diarylureas in yields up to 94%. A mechanism has been proposed to demonstrate the formation of symmetrical ureas.
- Wang, Xiaofang,Lu, Shiwei,Yu, Zhengkun
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- Copper catalyzed ipso-nitration of iodoarenes, bromoarenes and heterocyclic haloarenes under ligand-free conditions
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A catalytic protocol for the conversion of haloarenes into the corresponding nitroarenes is presented using copper salts under ligand-free conditions. The method was effectively utilized for the ipso-nitration of a broad variety of haloarenes that includes iodoarenes, bromoarenes, and heterocyclic haloarenes.
- Amal Joseph,Priyadarshini,Lakshmi Kantam,Maheswaran
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- Convenient dimethylamino amination in heterocycles and aromatics with dimethylformamide
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A convenient dimethylamino amination of various heterocyclic and aromatic compounds having activated chloro group has been carried out in good yields using dimethyl formamide (DMF).
- Agarwal, Anu,Chauhan, Prem M. S.
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- Methylation of aromatic amines and imines using formic acid over a heterogeneous Pt/C catalyst
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We describe here a commercially available Pt/C catalyst capable of catalyzing the methylation of anilines and aromatic imines with formic acid in the presence of a hydrosilane reductant. Both primary aniline and secondary aniline can be methylated. The advantage of this newly described method includes operational simplicity, high TON, ready availability of the catalyst, and also good functional group compatibility.
- Zhu, Lei,Wang, Lian-Sheng,Li, Bojie,Li, Wei,Fu, Boqiao
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- Efficient and mild procedure for reductive methylation of amines using N-methylpiperidine zinc borohydride
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A simple and efficient procedure for reductive methylation of primary and secondary amines using N-methylpiperidine zinc borohydride (ZBNMPP), giving tertiary amines, is described. The reaction is carried out in methanol at room temperature under neutral conditions. Copyright Taylor & Francis Group, LLC.
- Alinezhad, Heshmatollah,Tajbakhsh, Mahmood,Zamani, Reza
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- Metal-free protodeboronation of electron-rich arene boronic acids and its application to ortho -functionalization of electron-rich arenes using a boronic acid as a blocking group
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The metal-free thermal protodeboronation of various electron-rich arene boronic acids was studied. Several reaction parameters controlling this protodeboronation, such as solvent, temperature, and a proton source, have been investigated. On the basis of these studies, suitable reaction conditions for protodeboronation of several types of electron-rich arene boronic acids were provided. On the basis of this protodeboronation, a new protocol for the synthesis of ortho-functionalized electron-rich arenes from these boronic acids was developed using the boronic acid moiety as a blocking group in the electrophilic aromatic substitution reaction, followed by the removal of the boronic acid moiety via thermal protodeboronation. Mechanistic studies suggested that this protodeboronation might proceed via the complex formation of a boronic acid with a proton source, followed by the carbon-boron bond fission through σ-bond metathesis, to afford the corresponding arene compound and boric acid.
- Ahn, Su-Jin,Lee, Chun-Young,Kim, Nak-Kyoon,Cheon, Cheol-Hong
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- Catalyst-free N-methylation of amines using CO2
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Recently, utilizing CO2 as a methylation reagent to construct functional chemicals has attracted significant attention. However, the conversion of CO2 is still a challenge due to its inherent inertness. In this study, we have developed a catalyst-free N-methylation of amines to prepare numerous methylamines using CO2 as a methyl source. By utilizing 2 eq. PhSiH3 as the reductant, amines could undergo N-methylation under 1 atm of CO2 in DMF at 90 °C. Aliphatic and aromatic amines were compatible, generating the desired products in up to 95% yield.
- Niu, Huiying,Lu, Lijun,Shi, Renyi,Chiang, Chien-Wei,Lei, Aiwen
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- A New Route for Synthesis of 2-Substituted-3-amino-5-phenyl-7-N,N-dimethylamino Phenazinium Chloride Salts
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2-Methyl-3-amino-5-phenyl-7-N, N-dimethylamino phenazinium chloride salts were synthesized in better yields via the cyclization of 4-amino-N,N-dimethylaniline with toluidine derivatives and aminobenzene under the oxidation of sodium bicarbonate.
- Liu, Yuan,Jin, Ling,Liu, Jun-Feng
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- 4-N,N-Dimethylaminophenyl azide photooxidation: effect of conditions on the reaction pathway. Ring contraction of benzene to cyclopentadiene due to a strongly electron-donating substituent
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Abstract Depending on the reaction conditions employed, the photooxidation of 4-N,N-dimethylaminophenyl azide led to the formation of 4-N,N-dimethylaminonitrosobenzene and 4-N,N-dimethylaminonitrobenzene or (5Z)-2-(dimethylamino)-5-(hydroxyimino)cyclopenta-1,3-diene-1-carbaldehyde.
- Chainikova, Ekaterina,Khursan, Sergey,Lobov, Alexander,Erastov, Alexey,Khalilov, Leonard,Mescheryakova, Ekaterina,Safiullin, Rustam
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- Transformation of N, N-Dimethylaniline N-Oxides into Diverse Tetrahydroquinoline Scaffolds via Formal Povarov Reactions
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A one-pot protocol for the assembly of diversely functionalized tetrahydro-, hexahydrofuro-, hexahydropyrano-, and tetrahydrobenzofuroquinolines from N,N-dimethylaniline N-oxides and various electron-rich olefins in a tandem Polonovski-Povarov sequence is reported. Following activation of the N-O bond with Boc2O, an exocyclic iminium ion is unveiled upon exposure to tin(IV) chloride. A formal inverse-electron-demand aza-Diels-Alder cyclization generates the tetrahydroquinoline core of 29 examples in up to 92% yield.
- Bush, Timothy S.,Yap, Glenn P. A.,Chain, William J.
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- Synthesis of dihydroquinazolines from 2-aminobenzylamine: N3-aryl derivatives with electron-withdrawing groups
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The sequential N-functionalization of 2-aminobenzylamine (2-ABA) followed by cyclodehydration allowed for a straightforward and efficient synthesis of 3,4-dihydroquinazolines with N-aryl substituents bearing electron-withdrawing groups. The sequence involves an initial SNAr displacement, N-acylation and MW-assisted ring closure. Remarkably, the uncatalyzed N-arylation of 2-ABA led to the monosubstitution product using equimolar amounts of both reagents. The individual steps were optimized achieving good to excellent overall yields of the desired heterocycles, avoiding additional protection and deprotection steps. A mechanistic interpretation for the cyclodehydration reaction promoted by trimethylsilyl polyphosphate (PPSE) is also proposed on the basis of literature data and our experimental observations.
- Gruber, Nadia,Díaz, Jimena E.,Orelli, Liliana R.
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- Iron catalyzed oxidative cyanation of tertiary amines
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Iron(ii) and iron(iii) salts catalyze the oxidative α-cyanation of tertiary amines by trimethylsilyl cyanide in the presence of tert-butylhydroperoxide under acid-free conditions at room temperature.
- Han, Wei,Ofial, Armin R.
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- Copper catalysis: Ligand-controlled selective: N -methylation or N -formylation of amines with CO2 and phenylsilane
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Cupric subcarbonate (Cu2(OH)2CO3) was found to be effective for the reductive functionalization of CO2 to produce formamides and methylamines with phenylsilane as reductant. Interestingly, N-formylation and N-methylation were switched on/off by subtly choosing the ligand: DPPB (1,4-bis(diphenylphosphino)butane) promoted N-methylation whereas Ph2CyP (diphenylcyclohexylphosphine) favored for N-formylation.
- Li, Xue-Dong,Xia, Shu-Mei,Chen, Kai-Hong,Liu, Xiao-Fang,Li, Hong-Ru,He, Liang-Nian
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- Catalytic alternative of the Ullman reaction
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Symmetrical functionalized biaryls and biheterocycles could be obtained in good yield via homocoupling of aryl halides by using Pd(OAc)2 as catalyst with base and isopropanol. This alternative of the Ullmann reaction has proved to be compatible with sensitive functional groups.
- Hassan, Jwanro,Penalva, Vincent,Lavenot, Laurence,Gozzi, Christel,Lemaire, Marc
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- NITROPHENYL ETHERS AS POSSIBLE PHOTOAFFINITY LABELS. THE NUCLEOPHILIC AROMATIC PHOTOSUBSTITUTION REVISITED.
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The photoreactions of nitrophenyl ethers with simple primary and secondary amines show a remarkable nucleophile influence on the reaction orientation.Calculations indicate a change from charge controlled to frontier orbital controlled reactions moving from smaller to larger amines.
- Cervello, J.,Figueredo, M.,Marquet, J.,Moreno-Manas, M.,Bertran, J.,Lluch, J. M.
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- Base-oxidant promoted metal-free N-demethylation of arylamines
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A metal-free oxidative N-demethylation of arylamines with triethylamine as a base and tert-butyl hydroperoxide (TBHP) as oxidant is reported in this paper. The reaction is general, practical, inexpensive, non-toxic, and the method followed is environmentally benign, with moderate to good yields. [Figure not available: see fulltext.]
- Botla, Vinayak,Barreddi, Chiranjeevi,Daggupati, Ramana V,Malapaka, Chandrasekharam
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- Celite-Polyaniline supported palladium catalyst for chemoselective hydrogenation reactions
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Polyaniline coated on particles of celite is used as support to load palladium catalyst. This heterogenized Celite?PANI?Pd system, is used as an efficient catalyst for chemoselective hydrogenation reactions. The catalyst is characterized by usual spectral, analytical techniques and studied for hydrogenation reactions at ambient conditions. The mild reaction conditions allow the control over the reactions and excellent selectivity is achieved in number of conversions. Hydrogenation of a carbon–carbon double bond was favored over other polar π-bond systems, while labile functional groups such as benzyl ether, benzyl esters, cyano, nitro and halogen remained unaffected. Primary amines were converted to N,N-dimethyl amines with formaldehyde, the double bond of coumarin was selectively hydrogenated without opening of the lactone functionality.
- Patel, Heta A.,Rawat, Maitreyee,Patel, Arun L.,Bedekar, Ashutosh V.
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- New nitronate σ complexes and the mechanism of nucleophilic aromatic photosubstitution para to a nitro group
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Photolysis of 4-nitroanisole with aliphatic amines gives mainly N-substituted 4-nitroanilines. Reactions of this type have been widely attributed to a geminate radical mechanism. We questioned this interpretation and have searched for and found by NMR spectroscopy a new class of stable nitronate adducts generated under the reaction conditions. The adducts imply that photosubstitution by amines para to the nitro group occurs by meta σ complex formation followed by an unprecedented sigmatropic rearrangement.
- Wubbels, Gene G.,Johnson, Kandra M.
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- Borane-Trimethylamine Complex as a Reducing Agent for Selective Methylation and Formylation of Amines with CO2
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We report herein that a borane-trimethylamine complex worked as an efficient reducing agent for the selective methylation and formylation of amines with 1 atm CO2 under metal-free conditions. 6-Amino-2-picoline serves as a highly efficient catalyst for the methylation of various secondary amines, whereas in its absence, the formylation of primary and secondary amines was achieved in high yield with high chemoselectivity. Mechanistic studies suggest that the 6-amino-2-picoline-borane catalytic system operates like an intramolecular frustrated Lewis pair to activate CO2.
- Zhang, Yanmeng,Zhang, He,Gao, Ke
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supporting information
p. 8282 - 8286
(2021/10/25)
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- Optimization of WZ4003 as NUAK inhibitors against human colorectal cancer
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NUAK, the member of AMPK (AMP-activated protein kinase) family of protein kinases, is phosphorylated and activated by the LKB1 (liver kinase B1) tumor suppressor protein kinase. Recent work has indicated that NUAK1 is a key component of the antioxidant stress response pathway, and the inhibition of NUAK1 will suppress the growth and survival of colorectal tumors. As a promising target for anticancer drugs, few inhibitors of NUAK were developed. With this goal in mind, based on NUAK inhibitor WZ4003, a series of derivatives has been synthesized and evaluated for anticancer activity. Compound 9q, a derivative of WZ4003 by removing a methoxy group, was found to be the most potential one with stronger inhibitory against NUAK1/2 enzyme activity, tumor cell proliferation and inducing apoptosis of tumor cells. By in vivo efficacy evaluations of colorectal SW480 xenografts, 9q suppresses tumor growth more effectively with an excellent safety profile in vivo and is therefore seen as a suitable candidate for further investigation.
- Yang, Huali,Wang, Xiaobing,Wang, Cheng,Yin, Fucheng,Qu, Lailiang,Shi, Cunjian,Zhao, Jinhua,Li, Shang,Ji, Limei,Peng, Wan,Luo, Heng,Cheng, Maosheng,Kong, Lingyi
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- CO2-tuned highly selective reduction of formamides to the corresponding methylamines
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We herein describe an efficient, CO2-tuned and highly selective C-O bond cleavage of N-methylated formanilides. With easy-to-handle and commercially available NaBH4 as the reductant, a variety of formanilides could be turned into the desired tertiary amines in moderate to excellent yields. The role of CO2 has been investigated in detail, and the mechanism is proposed on the basis of experiments.
- Chao, Jianbin,Guo, Zhiqiang,Pang, Tengfei,Wei, Xuehong,Xi, Chanjuan,Yan, Leilei
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supporting information
p. 7534 - 7538
(2021/10/12)
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- Photoassisted Charge Transfer Between DMF and Substrate: Facile and Selective N,N-Dimethylamination of Fluoroarenes
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A reversible Van der Waals complex formation between the electron-deficient fluorinated aromatic ring and N,N-dimethylformamide (DMF) molecules followed by light irradiation resulted in charge transfer (CT) process. The complex was stabilized by ammonium formate and further decomposed to form the C?N bond. Control experiments revealed that the simultaneous SNAr pathway also contributes to product formation. This methodology is mild, metal-free, and effective for the amination of a variety of substrates. The reproducibility of this methodology was also verified on gram-scale reactions. The CT states were supported by control UV/Vis spectroscopy and computational studies.
- Ansari, Tharique N.,Sharma, Sudripet,Bora, Pranjal P.,Ogulu, Deborah,Parmar, Saurav,Gallou, Fabrice,Kozlowski, Pawel M.,Handa, Sachin
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p. 2704 - 2709
(2021/06/09)
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- Catalyst-free selective: N -formylation and N -methylation of amines using CO2 as a sustainable C1 source
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We herein describe catalyst-free selective N-formylation and N-methylation of amines using CO2 as a sustainable C1 source. By tuning the reaction solvent and temperature, the selective synthesis of formamides and methylamines is achieved in good to excellent yields using sodium borohydride (NaBH4) as a sustainable reductant.
- Zou, Qizhuang,Long, Guangcai,Zhao, Tianxiang,Hu, Xingbang
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supporting information
p. 1134 - 1138
(2020/03/11)
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- Phenazine-Based Donor Acceptor Systems as Organic Photocatalysts for "metal-free" C-N/C-C Cross-Coupling
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With an aim to achieve a balance between ground-state and excited-state reduction potential of donor acceptor systems for efficient C-N/C-C cross-coupling, a series of donor acceptor systems DA1-DA4 have been synthesized by varying the donor strength and connecting positions. With an increase in donor strength, systematic elevation in the ground-state reduction potential and decrease in the HOMO-LUMO gap was observed. Interestingly, all the derivatives DA1-DA4 could catalyze the C-N bond formation reaction between activated aryl halides and amines at low catalytic loading under metal-free conditions without the need of any external base upon irradiation with white LED. A balance was realized in the case of derivative DA2, which exhibits high efficiency in C-N couplings. Different control experiments support the validity of the energy as well as electron transfer pathways in the visible light-mediated C-N bond formation. This study further reveals the potential of derivative DA1 in "metal-free"Sonogashira coupling involving activated aryl halides which is attributed to its high excited-state reduction potential.
- Deol, Harnimarta,Singh, Gurpreet,Kumar, Manoj,Bhalla, Vandana
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p. 11080 - 11093
(2020/10/12)
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- WEE1 inhibitors as well as preparation and application thereof
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The invention relates to WEE1 inhibitors as well as preparation and application thereof. The present invention relates to compounds of formula (I), or pharmaceutically acceptable salts, solvates, polymorphs or isomers thereof, and their use in the preparation of medicaments for the treatment of diseases associated with WEE1 activity.
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Paragraph 0726-0732
(2020/10/14)
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- NITRATION
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The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.
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Page/Page column 36; 41; 46; 64; 37; 43; 48; 68
(2020/05/28)
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- UiO-type metal-organic frameworks with NHC or metal-NHC functionalities for: N-methylation using CO2 as the carbon source
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We demonstrate the first metal-organic framework (MOF) that catalyzes N-methylation of amines using 1 atm CO2 and phenylsilane under ambient conditions. Compared with its homogeneous analog, the incorporation of N-heterocyclic carbene (NHC) into the MOF provides more efficient catalysis with improved reaction kinetics, turnover numbers and recyclability. Moreover, the metalated NHC functionalized MOF achieves direct N-methylation of amines bearing carboxylate moieties, which are common building blocks in pharmaceutical chemistry.
- Zhang, Xu,Jiang, Yilin,Fei, Honghan
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supporting information
p. 11928 - 11931
(2019/10/11)
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- Eco-friendly acetylcholine-carboxylate bio-ionic liquids for controllable: N-methylation and N-formylation using ambient CO2 at low temperatures
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Catalytic fixation of CO2 to produce valuable fine chemicals is of great significance to develop a green and sustainable circulation of excessive carbon in the environment. Herein, a series of non-toxic, biodegradable and recyclable acetylcholine-carboxylate bio-ionic liquids with different cations and anions were simply synthesized for producing formamides and methylamines using atmospheric CO2 as a carbon source, and phenylsilane as a hydrogen donor. The selectivity toward products was tuned by altering the reaction temperature under solvent or solvent-free conditions. N-Methylamines (ca. 96% yield) were obtained in acetonitrile at 50 °C, while N-formamides (ca. 99% yield) were attained without a solvent at 30 °C. The established bio-ionic liquid catalytic system found a wide range of applicability in substrates and possessed a high potentiality in scale-up to gram-grade production. The developed catalytic system was fairly stable, which could be easily reused without an apparent loss of reactivity, possibly due to the strong electrostatic interactions between the cation and anion. The combination of experimental and computational results explicitly elucidated the reaction mechanism: PhSiH3 activated by a bio-IL was favorable for the formation of silyl formate from hydrosilylation of CO2, followed by a reaction with an amine to give an N-formamide, while an N-methylamine was formed by further hydrosilylation of the N-formamide.
- Zhao, Wenfeng,Chi, Xiaoping,Li, Hu,He, Jian,Long, Jingxuan,Xu, Yufei,Yang, Song
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supporting information
p. 567 - 577
(2019/02/14)
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- Method for preparing important chemicals by using lignin as methyl sources
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The invention relates to preparation of important chemical products by using methoxyl groups in lignin. According to a method, methyl provided by the lignin reacts with carbon monoxide and water underthe catalysis effects of catalysts to obtain acetic acid; reaction is performed with aminated compounds to obtain N-methylation products. The methoxyl groups in the lignin are used for preparing important chemical products for the first time; an important and continuous production path is provided for the preparation of various important chemical products.
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Paragraph 0097; 0098; 0120-0124
(2019/06/12)
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- Design, synthesis and biological evaluation of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivative as potent antitumor agents
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To develop novel therapeutic agents with anticancer activities, two series of novel 7-amino-[1,2,4]triazolo[4,3-f]pteridinone, and 7-aminotetrazolo[1,5-f]pteridinone derivatives were designed and synthesized. All compounds were tested for anti-proliferative activities against five cancer cell lines. The structure-activity relationships (SARs) studies were conducted through the variation in two regions, the moiety of A ring and the terminal aniline B on pteridinone core. 1-Methyl-1,2,4-triazole derivative L7 with 2,6-dimethylpiperazine showed the most potent antiproliferative activity against A549, PC-3, HCT116, MCF-7 and MDA-MB-231 cell lines with IC50 values of 0.16 μM, 0.30 μM, 0.51 μM, 0.30 μM, and 0.70 μM, respectively. Combined with the results of the molecular docking and enzymatic studies, the PLK1 was very likely to be one of the drug targets of compound L7. Furthermore, to clarify the anticancer mechanism of compound L7, further explorations in the bioactivity were conducted. The results showed that compound L7 obviously inhibited proliferation of A549 cell lines, induced a great decrease in mitochondrial membrane potential leading to apoptosis of cancer cells, suppressed the migration of tumor cells, and arrested G1 phase of A549 cells.
- Hou, Yunlei,Zhu, Liangyu,Li, Zhiwei,Shen, Qi,Xu, Qiaoling,Li, Wei,Liu, Yajing,Gong, Ping
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p. 690 - 709
(2019/01/04)
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- Design, synthesis and biological evaluation of novel 2,4-diaminopyrimidine derivatives as potent antitumor agents
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For developing novel therapeutic agents with anticancer activities, two series of novel 2,4-diaminopyrimidine derivatives possessing triazolopiperazine or 1,4,8-triazaspiro[4.5]decan-3-one scaffolds were designed and synthesized. Preliminary investigations showed that some compounds exhibited moderate to excellent potency against four tested cancer cell lines as compared with palbociclib and momelotinib. In particular, the most promising compounds 9k and 13f showed the most potent antitumor activities with IC50 values of 2.14/1.98 μM, 3.59/2.78 μM, 5.52/4.27 μM, and 3.69/4.01 μM against A549, HCT-116, PC-3 and MCF-7 cell lines, respectively. Structure-activity relationship (SAR) studies were conducted based on the variation of the moiety of the aromatic ring and the terminal aniline on the pyrimidine core. Furthermore, the mechanism of their anticancer activity was clarified by further exploring the bioactivity. The results showed that compound 9k obviously inhibited the proliferation of A549 cell lines, induced a great decrease in the mitochondrial membrane potential leading to apoptosis of cancer cells, suppressed the migration of tumor cells and prolonged the A549 cell cycle distribution, representing blockage at the G2-M phase and accumulation at the S phase.
- Hu, Gang,Wang, Chu,Xin, Xin,Li, Shuaikang,Li, Zefei,Zhao, Yanfang,Gong, Ping
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p. 10190 - 10202
(2019/07/03)
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- Amination of Aromatic Halides and Exploration of the Reactivity Sequence of Aromatic Halides
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A base-promoted amination of aromatic halides has been developed using a limited amount of dimethylformamide (DMF) or amine as an amino source. Various aryl halides, including F, Cl, Br, and I, have been successfully aminated in good to excellent yields. Although the amination of aromatic halides with amines or DMF is usually considered as an aromatic nucleophilic substitution (SNAr) process, and the reactivity of an aromatic halide is F > Cl > Br > I, the reactivity of aromatic halides in this system was found to be I > Br a‰ F > Cl. This protocol also showed a good regioselectivity for multihalogenated aromatics. This protocol is valuable for industrial application due to the simplicity of operation, the unrestricted availability of amino sources and aromatic halides, transition metal-free conditions, no requirement for solvent, and scalability.
- Yang, Chu,Zhang, Feng,Deng, Guo-Jun,Gong, Hang
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p. 181 - 190
(2019/01/10)
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- Iron-Catalyzed Selective N-Methylation and N-Formylation of Amines with CO2
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We herein describe an efficient iron-catalyzed selective N-methylation and N-formylation of amines with CO2 and silane using mono-phosphine as ligand. With commercially available [CpFe(CO)2]2 as catalyst, Fe-catalyzed methylation of amines was achieved with triphenylphosphine as a ligand. Using tributylphosphine as a ligand, Fe-catalyzed formylation of amines was realized at a lower temperature. The method was successfully applied in the late-stage methylation and formylation of drug molecules containing amine moiety. (Figure presented.).
- Li, Wen-Duo,Zhu, Dao-Yong,Li, Gang,Chen, Jie,Xia, Ji-Bao
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supporting information
p. 5098 - 5104
(2019/11/03)
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- Method for preparing formamide and N-methylamines by carrying out selective reduction on carbon dioxide and amines regulated by ligand
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The invention relates to a method for preparing formamide and N-methylamines by carrying out selective reduction on carbon dioxide and amines regulated by a ligand. According to the method, copper salt is used as a catalyst, organic amine or organic phosphorus is used as the ligand, CO2 and a hydrosilane are respectively used as a C1 resource and a reducing agent, and amines are used as a nucleophilic reagent; a reaction is carried out in an organic solvent, the consumption of the catalyst is 1-5mol%, and the consumption of the ligand is 1-20 mol%, the reaction temperature is 20-80 DEG C, theCO2 pressure is 0.1-8.0 MPa, the reaction time is 10-48h, the highest yield of the formamide is up to 98%, and the highest yield of the N-methylamine is up to 95%. The method provided by the inventionhas the advantages that the ligand is used for a regulation method for selective reduction preparation of the formamide and the N-methylamines for the first time; the catalyst is low in price, easy to obtain and simple in composition; the renewable CO2 is used as a raw material, so that the use of the traditional toxic formylation and methylation reagents is avoided; the substrate is wide in application scope and is suitable for a variety of secondary amines.
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Paragraph 0135-0142
(2019/01/14)
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- Mechanical force under the action of the nitration of aromatic compounds of nitrate method (by machine translation)
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The invention discloses a mechanical force under the action of the nitration of aromatic compounds of nitrate method. The invention provides a method for preparing aromatic nitro compounds, comprising the following steps: under the action of mechanical force, aromatic compound with a metal nitrate or its hydrate by the nitration reaction, to obtain the aromatic nitro compound; the mechanical fastener is machinery offers can cause material physical and/or chemical nature of the change of the external force. The mechanical force can be compression, shear, impact, friction, tensile, bending and vibration of any kind. The invention has the following advantages: without the use of any solvent, thereby avoiding the waste liquid produced; and without the use of the acidic substance, the reaction is complete after treatment is simple, without any damage to the apparatus; a very high conversion and selectivity, can be applied to the nitration of conventional aromatic compound. (by machine translation)
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Paragraph 0062; 0063
(2018/09/11)
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- Base-promoted nucleophilic fluoroarenes substitution of C–F bonds
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With the use of KOH/DMSO as the superbase medium, the nucleophilic fluoroarene substitution for C–F bonds is presented. The transformation proceeds smoothly with the use of fluoroarenes bearing not only electron-withdrawing group, but also electron-donating group and a variety of nucleophiles such as alcohols, phenols, amines, amides and nitrogen-heterocyclic compounds. The double nucleophilic substitution using ortho-difluoroarenes and nucleophiles bearing ortho-dinucleophilic groups results in the formation of 2,3-dihydro-1,4-benzodioxins, dibenzo[b,e][1,4]dioxins and 10H-phenoxazines in moderate to good yields.
- Su, Ji,Chen, Qian,Lu, Le,Ma, Yuan,Auyoung, George Hong Lok,Hua, Ruimao
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supporting information
p. 303 - 307
(2017/12/11)
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- Deoxygenation of tertiary amine N-oxides under metal free condition using phenylboronic acid
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A simple and efficient method for the deoxygenation of amine N-oxides to corresponding amines is reported using the green and economical reagent phenylboronic acid. Deoxygenation of N,N-dialkylaniline N-oxides, trialkylamine N-oxides and pyridine N-oxides were achieved in good to excellent yields. The reduction susceptible functional groups such as ketone, amide, ester and nitro groups are well tolerated with phenylboronic acid during the deoxygenation process even at high temperature. In addition, an indirect method for identification and quantification of tert-amine N-oxide is demonstrated using UV–Vis spectrometry which may be useful for drug metabolism studies.
- Gupta, Surabhi,Sureshbabu, Popuri,Singh, Adesh Kumar,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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supporting information
p. 909 - 913
(2017/02/15)
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- Highly efficient protocol for the aromatic compounds nitration catalyzed by magnetically recyclable core/shell nanocomposite
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An efficient protocol for the nitration of aromatic compounds in the presence of a catalytic amount of sulfuric acid-functionalized silica-based magnetic core/shell nanocomposite was reported. The designed products were obtained in high yields in relatively short reaction times at room temperature under solvent-free conditions. The nanocatalyst was simply recovered from the reaction mixture by using an external magnet and efficiently reused for several times. The characterization of particle size, morphology and elemental analysis of the nanocatalyst were provided by scanning electron microscopy, transmission electron microscopy and energy-dispersive X-ray spectroscopy analyses, respectively.
- Maleki, Ali,Aghaei, Morteza,Paydar, Reza
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p. 485 - 490
(2017/01/10)
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- Discovery of Potent, Selective Stem Cell Factor Receptor/Platelet Derived Growth Factor Receptor Alpha (c-KIT/PDGFRα) Dual Inhibitor for the Treatment of Imatinib-Resistant Gastrointestinal Stromal Tumors (GISTs)
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Stem cell factor receptor (c-KIT) and platelet derived growth factor receptor alpha (PDGFRα) kinases play an important role in gastrointestinal stromal tumors (GISTs). Here, we have discovered an c-KIT/PDGFRα dual inhibitor, compound 31, with single-digit nanomolar potency against c-KIT and PDGFRα. Compared to Imatinib (1), 31 showed better antiproliferative efficacy against various TEL-c-KIT/PDGFRα-BaF3 isogenic cells, including three 1-resistant BaF3 cell lines, as well as against GIST-T1 and GIST-882 cell lines. Furthermore, compound 31 showed a good KinomeScan selectivity (468 kinases) (S score (1) = 0.01 at 1 μM concentration), good metabolic stability in liver microsomes, and no hERG inhibitory activity. It was worth noting that 31 inhibited GIST-T1 tumor growth (TGI = 81.5%) and even the BaF3-TEL-cKIT-T670I tumor progression (TGI = 41.9%, 1-resistant GISTs) at a dosage of 100 mg/kg/day without exhibiting apparent toxicity.
- Lu, Yanli,Mao, Fei,Li, Xiaokang,Zheng, Xinyu,Wang, Manjiong,Xu, Qing,Zhu, Jin,Li, Jian
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supporting information
p. 5099 - 5119
(2017/06/28)
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- Preparation method by using amine and imine nitrogen methylation and application thereof
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The invention discloses a preparation method by using amine and imine nitrogen methylation and application thereof. The preparation method comprises the following steps: A, adding an active carbon loaded platinum catalyst into a Schlenk tube, and after vacuumizing to replace argon, adding a solvent; B, under protection of argon, separately adding phenylsilane, an initial raw material and formic acid; C, stirring the whole reaction system at a certain temperature to react; and D, after reaction, adding ethyl acetate into the system to dilute, stopping the reaction by using a sodium hydroxide aqueous solution, performing extraction with ethyl acetate, separating out an organic phase, drying and filtering the organic phase, and performing rotatable evaporation to remove the solvent. Column chromatography is performed on residues by using ethyl acetate/petroleum ether mixed solvent to obtain a target product, wherein the ethyl acetate and petroleum ether are different in proportion. According to the application of the method in isotope labeled drug synthesis, the dosage of a catalyst is extremely low, the cost is quite low, and the method is suitable for large-scaled production, can be suitable for amine and imine with different substituents, and suitable for realizing methylation conveniently on nitrogen atoms in a natural product structure to prepare drug molecules.
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Paragraph 0151; 0152; 0153; 0154; 0155; 0156
(2017/08/10)
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- N-Methylation of poorly nucleophilic aromatic amines with dimethyl carbonate
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Abstract: Dimethyl carbonate (DMC), an environmentally friendly methylation agent, is a substitute for traditional methylation agents such as methyl halides (CH3X, X?=?I, Br, Cl) or dimethyl sulfate. An efficient, convenient, and green method has been developed for N-methylation of poorly nucleophilic aromatic amines with DMC. It was found that the couple PEG400/K2CO3 provides good selectivity for the N-methylation product. Finally, the mechanism for reaction of amines with DMC was investigated, and a plausible multistep mechanism proposed and verified. Graphical Abstract: [Figure not available: see fulltext.]
- Yan, Huidong,Zeng, Liufang,Xie, Yaqiang,Cui, Yu,Ye, Liyi,Tu, Song
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p. 5951 - 5960
(2016/06/01)
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- General method for nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine using hydroxide-assisted decomposition of N,N-dimethylforamide
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A practical and convenient procedure for the nucleophilic aromatic substitution of aryl fluorides and chlorides with dimethylamine was developed using a hydroxide-assisted thermal decomposition of N,N-dimethylforamide. These conditions are tolerant of nitro, nitrile, aldehyde, ketone, and amide groups but will undergo acyl substitution to form amides for methyl esters and acyl chlorides. Isolated yields of the products range from 44% to 98%, with the majority being greater than 70% for 17 examples.
- Garcia, Juana,Sorrentino, Jacob,Diller, Emily J.,Chapman, Daniel,Woydziak, Zachary R.
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supporting information
p. 475 - 481
(2016/04/05)
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- Methylation of aniline and its derivatives with dimethyl carbonate in the presence of binder-free micro-, meso-, and macroporous zeolites KNaX, NaY, and HY
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Aniline and its derivatives undergo methylation when treated with dimethyl carbonate in the presence of binder-free micro-, meso-, and macroporous zeolites KNaX, NaY, and HY leading to the formation of N-methyl- and N,N-dimethylanilines.
- Khusnutdinov,Shchadneva,Mayakova, Yu. Yu.,Ardieva,Khazipova,Kutepov
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p. 1565 - 1570
(2017/01/28)
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- N-methyl-2-chloropyridinium iodide/NaNO2/Wet SiO2: Neutral reagent system for the nitration of activated aromatic compounds under very mild conditions
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Mononitration of activated aromatic compounds using N-methyl-2-chloro-pyridinium iodide (Mukaiyama reagent)/NaNO2/wet SiO2 reagent system under neutral, very mild and environmentally safer reaction condition has been developed. Various structurally diverse aromatic rings are subjected in this condition and the corresponding nitro-aromatic compounds are prepared in moderately high yields.
- Azadi, Roya,Nazari-Far, Zahra
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p. 136 - 140
(2015/06/22)
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- Room-temperature copper-catalyzed arylation of dimethylamine and methylamine in neat water
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The first room-temperature copper-catalyzed arylations of dimethylamine and methylamine in neat water have been developed. Using a combination of CuI and 6,7-dihydroquinolin-8(5 H)-one oxime as catalyst, dimethylamine is arylated with various aryl halides to give the corresponding products in good to excellent yields. Further, this catalysis enables the selective arylation of methylamine to afford the high yields of monoarylated methylamines as the sole products.
- Wang, Deping,Kuang, Daizhi,Zhang, Fuxing,Yang, Chunlin,Zhu, Xiaoming
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supporting information
p. 714 - 718
(2015/03/18)
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- Boron-Catalyzed N-Alkylation of Amines using Carboxylic Acids
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A boron-based catalyst was found to catalyze the straightforward alkylation of amines with readily available carboxylic acids in the presence of silane as the reducing agent. Various types of primary and secondary amines can be smoothly alkylated with good selectivity and good functional-group compatibility. This metal-free amine alkylation was successfully applied to the synthesis of three commercial medicinal compounds, Butenafine, Cinacalcet. and Piribedil, in a one-pot manner without using any metal catalysts.
- Fu, Ming-Chen,Shang, Rui,Cheng, Wan-Min,Fu, Yao
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supporting information
p. 9042 - 9046
(2015/08/03)
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- Iron(III)-catalyzed C-H functionalization: Ortho-benzoyloxylation of N,N-dialkylanilines and its application to 1,4-benzoxazepines
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A C-O bond-formation reaction that proceeds through C-H functionalization of N,N-dialkylanilines at the ortho-position is presented. The iron-catalyzed selective ortho-benzoyloxylation follows a polar Friedel-Crafts-like mechanism and is sensitive to the nucleophilicity of the anilines. The benzoyl-oxylation of a variety of N,N-disubstituted anilines and Nphenyl heterocycles is carried out under extremely mild conditions. Furthermore, the methodology has been successfully employed for the generation of 1,4-benzoxazepines and oaminophenols.
- Chiranjeevi, Barreddi,Vinayak, Botla,Parsharamulu, Thupakula,PhaniBabu, Vemulapalli S.,Jagadeesh, Bharatam,Sridhar, Balasubramanian,Chandrasekharam, Malapaka
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p. 7839 - 7849
(2015/01/16)
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- Metal-free catalyst for the chemoselective methylation of amines using carbon dioxide as a carbon source
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N-methylation of amines is an important step in the synthesis of many pharmaceuticals and has been widely applied in the preparation of other key intermediates and chemicals. Therefore, the development of efficient methylation methods has attracted considerable attention. In this respect, carbon dioxide is an attractive C1 building block because it is an abundant, renewable, and nontoxic carbon source. Consequently, we developed a highly chemoselective, metal-free catalytic system that operates under ambient conditions for the N-methylation of amines. The methylation of amines with CO2 as C1 source and Ph2SiH2 as reducing agent was achieved with an N-heterocyclic carbene (NHC) as the catalyst. The catalyst is tolerant toward a variety of functional groups (including esters and ethers, nitro, nitrile, and carbonyl groups, and unsaturated C-C bonds); the reaction uses commercially available reagents and can be performed on a gram scale.
- Das, Shoubhik,Bobbink, Felix D.,Laurenczy, Gabor,Dyson, Paul J.
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supporting information
p. 12876 - 12879
(2016/02/18)
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- Ligand free open air copper(II) mediated aryl formamidation and amination of aryl halides
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A simple synthetic procedure for direct formamidation and amination of aryl halides mediated by copper(II) salts was developed in open air, without an external ligand in formamide with potassium carbonate as a base. This approach is particularly efficient when electron active aryl halides are used as substrates. In these cases almost quantitative formamidation was observed.
- Komati, Rajesh,Jursic, Branko S.
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p. 1523 - 1527
(2014/03/21)
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