- Quinolin-8-yl Formate: A New Option for Small-Scale Carbonylation Reactions in Microwave Reactors
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A convenient procedure for conducting small-scale carbonylations of aryl or benzyl halides in a microwave reactor by using quinolin-8-yl formate is described. The resulting 8-acyloxyquinolines were shown to be more reactive than phenyl esters in acyl-tran
- Maddocks, Christopher J.,Aathimanikandan, Sivakumar V.,Richardson, Jeffery,Ruble, J. Craig
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p. 1608 - 1612
(2020/09/09)
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- Copper-Catalyzed Aerobic Oxidative [2 + 3] Cyclization/Aromatization Cascade Reaction: Atom-Economical Access to Tetrasubstituted 4,5-Biscarbonyl Imidazoles
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An atom-economical method for accessing tetrasubstituted 4,5-biscarbonylimidazoles by reaction between glycine derivatives and 5-alkoxyoxazoles is reported. The method, which involves a copper-catalyzed aerobic oxidative [2 + 3] cyclization/aromatization
- Xie, Jialin,Huang, Yuanqiong,Song, Hongjian,Liu, Yuxiu,Wang, Qingmin
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supporting information
p. 6056 - 6059
(2017/11/27)
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- Palladium-Catalyzed Oxidative Carbonylation of Aryl Hydrazines with CO and O2 at Atmospheric Pressure
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Palladium-catalyzed aerobic oxidative aminocarbonylation and alkoxycarbonylation reactions with aryl hydrazines as coupling partners have been developed. The oxidative carbonylation of aryl hydrazines proceeded smoothly at atmospheric pressure CO, employi
- Tu, Yongliang,Yuan, Lin,Wang, Tao,Wang, Changliu,Ke, Jiamei,Zhao, Junfeng
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p. 4970 - 4976
(2017/05/12)
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- A chiral cobalt(II) complex catalyzed asymmetric formal [3+2] cycloaddition for the synthesis of 1,2,4-triazolines
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A highly efficient catalytic asymmetric formal [3+2] cycloaddition reaction of 5-alkoxyoxazoles with azodicarboxylate compounds has been realized by a chiral N,N′-dioxide/Co(BF4)2·6H2O complex. A series of poly-substituted 1,2,4-triazolines compounds were obtained in moderate to excellent yields (70-99%) with excellent enantioselectivities (82-98% ee).
- Ma, Baiwei,Luo, Weiwei,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 4077 - 4079
(2017/04/13)
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- Catalytic, asymmetric, and stereodivergent synthesis of non-symmetric β,β-Diaryl-α-Amino Acids
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We report a concise, enantio- and diastereoselective route to novel nonsymmetrically substituted N-protected β,β-diaryl-α-amino acids and esters, through the asymmetric hydrogenation of tetrasubstituted olefins, some of the most challenging examples in the field. Stereoselective generation of an E- or Z-enol tosylate, when combined with stereoretentive Suzuki-Miyaura cross-coupling and enantioselective hydrogenation catalyzed by (NBD)2RhBF4 and a Josiphos ligand, allows for full control over the two vicinal stereogenic centers. High yields and excellent enantioselectivities (up to 99% ee) were obtained for a variety of N-acetyl, N-methoxycarbonyl, and N-Boc β,β-diaryldehydroamino acids, containing a diverse and previously unreported series of heterocyclic and aryl substituted groups (24 examples) and allowing access to all four stereoisomers of these valuable building blocks.
- Molinaro, Carmela,Scott, Jeremy P.,Shevlin, Michael,Wise, Christopher,Mnard, Alain,Gibb, Andrew,Junker, Ellyn M.,Lieberman, David
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supporting information
p. 999 - 1006
(2015/01/30)
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- Palladium(II)-catalyzed ortho-C-H arylation/alkylation of N-benzoyl α-amino ester derivatives
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The palladium-catalyzed arylation/alkylation of ortho-C-H bonds in N-benzoyl α-amino ester derivatives is described. In such a system both the NH-amido and the CO2R groups in the α-amino ester moieties play a role in successful C-H activation/C-C bond formation using iodoaryl coupling partners. A wide variety of functional groups and electron-rich/ deficient iodoarenes are tolerated. The yields obtained range from 20 to 95 %. C-H activation: The transformation of N-benzoyl amino acid ester derivatives (Gly, Asp) has been studied, in which the ortho-C-H activation/C-C bond formation was achieved by using the synergistic system Pd(OAc)2/AgOAc and halide compounds as coupling partners in t-Amyl-OH under air (see scheme).
- Misal Castro, Luis C.,Chatani, Naoto
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p. 4548 - 4553
(2014/05/06)
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- COMPOUNDS FOR THE TREATMENT OF PARAMOXYVIRUS VIRAL INFECTIONS
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Disclosed herein are new antiviral compounds, together with pharmaceutical compositions that include one or more antiviral compounds, and methods of synthesizing the same. Also disclosed herein are methods of ameliorating and/or treating a paramyxovirus viral infection with one or more small molecule compounds. Examples of paramyxovirus infection include an infection caused by human respiratory syncytial virus (RSV).
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Paragraph 0320
(2014/03/25)
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- Magnetic CuFe2O4nanoparticles: A retrievable catalyst for oxidative amidation of aldehydes with amine hydrochloride salts
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The application of magnetic CuFe2O4nanoparticles for the oxidative amidation of aldehydes with amine hydrochloride salts is described. A wide range of amides have been synthesized in good to excellent yields under mild conditions. Chiral amide also synthesized from its corresponding chiral amine salt with retention of the stereochemistry. In particular, the performance of the magnetic separation of the catalyst was very efficient and an alternative to time, solvent and energy-consuming separation procedures. The catalytic activity of the catalyst remains unaltered after five consecutive cycles, making it environmentally benign and widely applicable due to its efficiency, ease of handling and cost effectiveness.
- Suresh Kumar,Thulasiram,Bala Laxmi,Rawat, Vikas S.,Sreedhar
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supporting information
p. 6059 - 6067
(2014/12/10)
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- Magnetic CuFe2O4 nanoparticles: A retrievable catalyst for oxidative amidation of aldehydes with amine hydrochloride salts
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The application of magnetic CuFe2O4 nanoparticles for the oxidative amidation of aldehydes with amine hydrochloride salts is described. A wide range of amides have been synthesized in good to excellent yields under mild conditions. Chiral amide also synthesized from its corresponding chiral amine salt with retention of the stereochemistry. In particular, the performance of the magnetic separation of the catalyst was very efficient and an alternative to time, solvent and energy-consuming separation procedures. The catalytic activity of the catalyst remains unaltered after five consecutive cycles, making it environmentally benign and widely applicable due to its efficiency, ease of handling and cost effectiveness.
- Suresh Kumar,Thulasiram,Bala Laxmi,Rawat, Vikas S.,Sreedhar
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supporting information
p. 6059 - 6067
(2015/03/30)
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- Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides
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A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide.
- Ghosh, Subhash Chandra,Ngiam, Joyce S. Y.,Seayad, Abdul M.,Tuan, Dang Thanh,Chai, Christina L. L.,Chen, Anqi
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p. 8007 - 8015,9
(2012/12/12)
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- Copper-catalyzed oxidative amidation of aldehydes with amine salts: Synthesis of primary, secondary, and tertiary amides
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A practical method for the amidation of aldehydes with economic ammonium chloride or amine hydrochloride salts has been developed for the synthesis of a wide variety of amides by using inexpensive copper sulfate or copper(I) oxide as a catalyst and aqueous tert-butyl hydroperoxide as an oxidant. This amidation reaction is operationally straightforward and provides primary, secondary, and tertiary amides in good to excellent yields for most cases utilizing inexpensive and readily available reagents under mild conditions. In situ formation of amine salts from free amines extends the substrate scope of the reaction. Chiral amides are also synthesized from their corresponding chiral amines without detectable racemization. The practicality of this amide formation reaction has been demonstrated in an efficient synthesis of the antiarrhythmic drug N-acetylprocainamide.
- Ghosh, Subhash Chandra,Ngiam, Joyce S.Y.,Seayad, Abdul M.,Tuan, Dang Thanh,Chai, Christina L.L.,Chen, Anqi
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p. 8007 - 8015
(2013/01/15)
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- Iron-catalyzed efficient synthesis of amides from aldehydes and amine hydrochloride salts
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A practical and efficient method for the synthesis of amides has been developed by iron-catalysed oxidative amidation of aldehydes with amine hydrochloride salts. A wide range of amides have been obtained in good to excellent yields under mild conditions. The application of this novel amide formation reaction to the synthesis of pharmaceutical compounds has been successfully demonstrated. Copyright
- Ghosh, Subhash Chandra,Ngiam, Joyce S. Y.,Chai, Christina L. L.,Seayad, Abdul M.,Dang, Tuan Thanh,Chen, Anqi
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supporting information; experimental part
p. 1407 - 1412
(2012/07/13)
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- Titanium-catalyzed stereoselective synthesis of spirooxindole oxazolines
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A regio-and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium (IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >
- Badillo, Joseph J.,Arevalo, Gary E.,Fettinger, James C.,Franz, Annaliese K.
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supporting information; experimental part
p. 418 - 421
(2011/04/15)
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- Synthesis and antiviral activities of novel acylhydrazone derivatives targeting HIV-1 capsid protein
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HIV-1 capsid protein (CA) plays important roles in the viral replication cycle. A number of acylhydrazone derivatives that act as inhibitors of HIV-1 CA assembly, were designed and synthesized. The synthesized compounds were tested for their antiviral activities and cytotoxicities using CEM cells. Some derivatives also were assayed for their ability to inhibit HIV-1 CA assembly in vitro. Among them, compounds 14f and 14i display the most promising potency with EC50 values of 0.21 and 0.17 μΜ, respectively.
- Tian, Baohe,He, Meizi,Tang, Shixing,Hewlett, Indira,Tan, Zhiwu,Li, Jiebo,Jin, Yinxue,Yang, Ming
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scheme or table
p. 2162 - 2167
(2009/12/25)
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- Evolution of the total syntheses of ustiloxin natural products and their analogues
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Ustiloxins A-F are antimitotic heterodetic cyclopeptides containing a 13-membered cyclic core structure with a synthetically challenging chiral tertiary alkyl-aryl ether linkage. The first total synthesis of ustiloxin D was achieved in 31 linear steps using an SNAr reaction. An NOE study of this synthetic product showed that ustiloxin D existed as a single atropisomer. Subsequently, highly concise and convergent syntheses of ustiloxins D and F were developed by utilizing a newly discovered ethynyl aziridine ring-opening reaction in a longest linear sequence of 15 steps. The approach was further optimized to achieve a better macrolactamization strategy. Ustiloxins D, F, and eight analogues (14-MeO-ustiloxin D, four analogues with different amino acid residues at the C-6 position, and three (9R,10S)-epi-ustiloxin analogues) were prepared via the second-generation route. Evaluation of these compounds as inhibitors of tubulin polymerization demonstrated that variation at the C-6 position is tolerated to a certain extent. In contrast, the S configuration of the C-9 methylamino group and a free phenolic hydroxyl group are essential for inhibition of tubulin polymerization.
- Li, Pixu,Evans, Cory D.,Wu, Yongzhong,Cao, Bin,Hamel, Ernest,Joullie, Madeleine M.
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p. 2351 - 2364
(2008/09/20)
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- Solid-phase synthesis of monocyclic β-lactam derivatives
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Liquid-phase studies concerning the solid-phase synthesis of monocyclic β-lactams via the esterenolate imine condensation route have been conducted utilizing triazene esters 1 and 2 as model compounds. Esters were attached to benzylamine resin 6 by a triazene linker employing the respective diazonium salts. Immobilized ester-enolates 8 and 10 were reacted with various imines and imine precursors to give polymer-bound β-lactams 14 and 17 in different substitution patterns. Traceless cleavage from the triazene linker yields the desired β-lactams 16 and 19.
- Schunk,Enders
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p. 8034 - 8042
(2007/10/03)
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- Site selectivity in the Rhodium(II)-catalyzed reaction of α-diazoimides. Ligand and substituent effects
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The product distribution obtained from Rh(II)-catalyzed decomposition of α-diazoimides derived from glycine methyl ester has been found to be selectively controlled by the proper choice of catalyst. When the reaction was carried out using perfluorinated l
- Prein, Michael,Manley, Peter J.,Padwa, Albert
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p. 7777 - 7794
(2007/10/03)
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- INDIRECT ELECTROCHEMICAL α-METHOXYLATION OF N-ACYL AND N-CARBOALKOXY α-AMINO ACID ESTERS AND APPLICATION AS CATIONIC GLYCINE EQUIVALENTS
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Indirect electrochemical methoxylation of N-acyl and N-carboalkoxy α-amino acid esters in α-position to nitrogen is possible, if chloride is used as mediator.The course of the reaction depends upon the protecting group as well as upon the amino acid side-chain.Increased electron withdrawing effects of the protecting group are accelerating the reaction.On the other hand aliphatic side-chains are diminishing the reactivity.High chloride ion concentrations improve the current yields surprisingly strong.
- Ginzel, Klaus-Dieter,Brungs, Peter,Steckhan, Eberhard
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p. 1691 - 1702
(2007/10/02)
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- Substrate Specificity and Stoichiometry of Nα-Benzyloxycarbonyl Amino Acid Urethane Hydrolase from Streptococcus faecalis R ATCC 8043
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The substrate specificity of a new enzyme, Nα-benzyloxycarbonyl amino acid urethane hydrolase, was investigated.The enzyme hydrolyzed Nα-benzyloxycarbonyl-glycine and -alanine, and Nα-benzoyl-glycine and -alanine.Nα-benzyloxycarbonyl-glycine was hydrolyzed to give equimolar benzyl alcohol and glycine.Equimolar benzoic acid and glycine were produced from Nα-benzoyl-glycine by the enzyme reaction.The Km, k0, and k0/Km values were measured for several substrates.The k0 values varied widely with the amino acid residues.Nα-benzyloxycarbonyl-glycine and Nα-benzoyl-glycine produced relatively small changes in the Km values (0.36 ca. 0.10 mM) and the k0/Km values (99440 ca. 202000 M-1 sec-1).The rate of hydrolysis is significantly affected by electron-supplying substituents on the benzene ring.
- Matsumura, Eiko,Shin, Takashi,Murao, Sawao,Kawano, Tatsu
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p. 973 - 980
(2007/10/02)
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