- Group 3 metal (Sc, La) triflates as catalysts for the carbomethoxylation of aliphatic amines with dimethylcarbonate under mild conditions
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The activity of Sc(OTf)3 and La(OTf)3 (OTf=SO 3CF3) as catalysts for the phosgene-free synthesis of carbamate esters via carbomethoxylation of aliphatic amines with dimethylcarbonate (DMC) has been investigated. In the presence of M(OTf) 3 (M=Sc, La), primary and secondary aliphatic amines easily react with dimethylcarbonate, under very mild conditions (20°C), to afford carbamate esters with good yield and excellent selectivity (?100%). Sc(OTf)3 is a more effective catalyst than the homologue La salt. The carbomethoxylation reaction requires as strict anhydrous conditions, as, at 20°C, the presence of water inhibits markedly the catalytic activity of both triflate salts. Temperature influences carbamate selectivity, which is lower at higher temperature because of deleterious formation of N-methylation side-products.
- Distaso, Monica,Quaranta, Eugenio
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Read Online
- Copper-Catalyzed Coupling of Amines with Carbazates: An Approach to Carbamates
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A new approach for the preparation of carbamatesviathe copper-catalyzed cross-coupling reaction of amines with alkoxycarbonyl radicals generated from carbazates is described. This environmentally friendly protocol takes place under mild conditions and is compatible with a wide range of amines, including aromatic/aliphatic and primary/secondary substrates.
- Wang, Song-Ning,Zhang, Guo-Yu,Shoberu, Adedamola,Zou, Jian-Ping
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p. 9067 - 9075
(2021/07/19)
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- Amine-Responsive Disassembly of AuI–CuI Double Salts for Oxidative Carbonylation
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A sensitive amine-responsive disassembly of self-assembled AuI-CuI double salts was observed and its utilization for the synergistic catalysis was enlightened. Investigation of the disassembly of [Au(NHC)2][CuI2] revealed the contribution of Cu-assisted ligand exchange of N-heterocyclic carbene (NHC) by amine in [Au(NHC)2]+ and the capacity of [CuI2]? on the oxidative step. By integrating the implicative information coded in the responsive behavior and inherent catalytic functions of d10 metal complexes, a catalyst for the oxidative carbonylation of amines was developed. The advantages of this method were clearly reflected on mild reaction conditions and the significantly expanded scope (51 examples); both primary and steric secondary amines can be employed as substrates. The cooperative reactivity from Au and Cu centers, as an indispensable prerequisite for the excellent catalytic performance, was validated in the synthesis of (un)symmetric ureas and carbamates.
- Cao, Yanwei,Yang, Jian-Gong,Deng, Yi,Wang, Shengchun,Liu, Qi,Shen, Chaoren,Lu, Wei,Che, Chi-Ming,Chen, Yong,He, Lin
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supporting information
p. 2080 - 2084
(2019/12/24)
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- Electrochemical Functional-Group-Tolerant Shono-type Oxidation of Cyclic Carbamates Enabled by Aminoxyl Mediators
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An electrochemical method has been developed for α-oxygenations of cyclic carbamates by using a bicyclic aminoxyl as a mediator and water as the nucleophile. The mediated electrochemical process enables substrate oxygenation to proceed at a potential that is approximately 1 V lower than the redox potential of the carbamate substrate. This feature allows for functional-group compatibility that is inaccessible with conventional Shono oxidations, which proceed by direct electrochemical substrate oxidation. This reaction also represents the first α-functionalization of non-activated cyclic carbamates with oxoammonium oxidants.
- Wang, Fei,Rafiee, Mohammad,Stahl, Shannon S.
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supporting information
p. 6686 - 6690
(2018/05/07)
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- Heterobimetallic dinuclear lanthanide alkoxide complexes as acid-base bifunctional catalysts for synthesis of carbamates under solvent-free conditions
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Heterobimetallic dinuclear lanthanide alkoxide complexes Ln2Na8(OCH2CH2NMe2)12(OH)2 [Ln: I (Nd), II (Sm), III (Yb) and IV (Y)] were used as efficient acid-base bifunctional catalysts for the synthesis of carbamates from dialkyl carbonates and amines as well as the N-Boc protection of amines. The cooperative catalysts showed high catalytic activity and a wide scope of substrates with good to excellent yields under solvent-free conditions. The systems have shown higher catalytic activities due to the noteworthy synergistic interactions of Lewis acid center-Br?nsted basic center. The comparison of catalytic efficiency between mono- and dinuclear heterobimetallic lanthanide alkoxide analogues was also investigated.
- Zeng, Ruijie,Bao, Linquan,Sheng, Hongting,Sun, Lili,Chen, Man,Feng, Yan,Zhu, Manzhou
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p. 78576 - 78584
(2016/09/09)
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- L-Proline-TBAB-catalyzed phosgene free synthesis of methyl carbamates from amines and dimethyl carbonate
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The reaction of amines and dimethyl carbonate (DMC) in the presence of catalytic amounts of l-proline and tetrabutylammonium bromide (TBAB) afforded methyl carbamates in good to excellent yields under mild conditions. The presence of both l-proline and TBAB co-catalysts is vital for this transformation.
- Kumar, Subodh,Jain, Suman L.
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p. 2935 - 2938
(2013/09/12)
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- Nitrogen-containing organobases as promoters in the cobalt(II)-Schiff base catalyzed oxidative carbonylation of amines
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The use of organic bases as promoters in the cobalt(II)-Schiff base complex catalyzed oxidative carbonylation of amines was investigated. The generality of the reaction was also studied by submitting different amines to the same procedure and by changing the reaction conditions. Very good yields in the corresponding ureas were achieved in toluene with a catalyst loading of 0.5 mol % and using TBD (1,5,7-triazabicyclo[4.4.0]dec-5-ene) as promoter. Methyl carbamates were obtained in methanol.
- Saliu, Francesco,Putomatti, Benedetto,Rindone, Bruno
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scheme or table
p. 3590 - 3593
(2012/09/08)
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- Photochemical rearrangement of N-mesyloxylactams: Stereospecific formation of N-heterocycles
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N-Mesyloxylactams undergo an efficient ring-contraction to N-heterocycles of various ring sizes. Yields increase with the degree of substitution α to the carbonyl. The stereochemical information of a chiral migrating carbon is conserved making this reacti
- Drouin, Alexandre,Winter, Dana K.,Pichette, Simon,Aubert-Nicol, Samuel,Lessard, Jean,Spino, Claude
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p. 164 - 169
(2011/03/19)
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- Carbamate synthesis from amines and dialkyl carbonate over inexpensive and clean acidic catalyst-Sulfamic acid
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Sulfamic acid has been proved to be the most efficient and recyclable catalyst in carbamate synthesis from alkylamine and dialkyl carbonate. High selectivity, cost-efficiency and simple product separation were the advantageous features obtained in this process. Sulfamic acid could be reused several times and keep its initial activity in the recycle runs. In addition, sulfamic acid has also exhibited the potential catalytic ability for alkylation of aromatic amines.
- Wang, Bo,He, Jing,Sun, Run Cang
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scheme or table
p. 794 - 797
(2011/11/13)
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- Indium-catalyzed reaction for the synthesis of carbamates and carbonates: selective protection of amino groups
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We developed a simple, efficient, and selective method for preparing organic carbamates and carbonates using a catalytic amount of indium. A wide range of carbamates and carbonates were synthesized in high yields. The method is also applicable to the selective protection of amino groups under mild conditions.
- Kim, Joong-Gon,Jang, Doo Ok
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experimental part
p. 2688 - 2692
(2009/08/09)
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- Mild and convenient synthesis of organic carbamates from amines and carbon dioxide using tetraethylammonium superoxide
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A safe and simple method of preparing organic carbamates has been achieved from amines and carbon dioxide using tetraethylammonium superoxide generated in situ. Copyright Taylor & Francis Group, LLC.
- Singh, Krishna Nand
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p. 2651 - 2654
(2008/02/12)
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- Ring contraction of N-chlorolactams, a novel rearrangement
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Upon photolysis in methylene chloride at -78 °C, different N-chlorolactams underwent a novel ring contraction to the corresponding carbamoyl chlorides, which were converted to the methyl carbamates. The rearrangement is 100% stereoselective, occurring with retention of configuration at the migrating carbon center. The yields of isolated carbamates ranged from 40% to 57%, the other product being the parent lactam, 18% to 38%.
- Drouin, Alexandre,Lessard, Jean
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p. 4285 - 4288
(2007/10/03)
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- Generation of carbon free radicals by reduction of the cation pool
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The electrochemical reduction of N-acyliminium ions, which were generated by the "cation pool" method, led to the formation of carbon free radicals. Carbon radicals thus generated underwent homo-coupling reactions and the reactions with activated olefins, such as methyl acrylate. In the latter case, a mechanism involving the addition of a carbon radical to the carbon-carbon double bond, followed by one-electron reduction to give carbanions, has been proposed. The present study opens a new possibility for radical-mediated carbon-carbon bond formation based on the reduction of carbocations.
- Suga, Seiji,Suzuki, Shinkiti,Maruyama, Tomokazu,Yoshida, Jun-Ichi
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p. 1545 - 1554
(2007/10/03)
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- Kinetics and mechanism of the aminolysis of methyl 4-nitrophenyl, methyl 2,4-dinitrophenyl, and phenyl 2,4-dinitrophenyl carbonates
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The reactions of methyl 4-nitrophenyl carbonate (MNPC) with a series of secondary alicyclic amines (SAA) and quinuclidines (QUIN), methyl 2,4-dinitrophenyl carbonate (MDNPC) with QUIN and 1-(2-hydroxyethyl)piperazinium ion (HPA), and phenyl 2,4-dinitrophenyl carbonate (PDNPC) with SAA are subjected to a kinetic investigation in aqueous solution, at 25.0°C and an ionic strength of 0.2 M. By following spectrophotometrically the nucleofuge release (330-400 nm) under amine excess, pseudo-first-order rate coefficients (kobsd) are obtained. Plots of kobsd VS [amine] at constant pH are linear, with the slope (kN) being pH independent. The Broensted-type plot (log kN vs amine pKa) for the reactions of SAA with MNPC is biphasic with slopes β1 = 0.3 (high pKa region) and β2 = 1.0 (low pKa region) and a curvature center at pKa0 = 9.3. This plot is consistent with a stepwise mechanism through a zwitterionic tetrahedral intermediate (T±) and a change in the rate-determining step with SAA basicity. The Broensted plot for the quinuclidinolysis of MNPC is linear with slope βN = 0.86, in line with a stepwise process where breakdown of T± to products is rate limiting. A previous work on the reactions of SAA with MDNPC was revised by including the reaction of HPA. The Broensted plots for the reactions of QUIN and SAA with MDNPC and SAA with PDNPC are linear with slopes β = 0.51, 0.48, and 0.39, respectively, consistent with concerted mechanisms. Since quinuclidines are better leaving groups from T± than isobasic SAA, yielding a less stable T±, it seems doubtful that the quinuclidinolysis of PDNPC is stepwise, as reported.
- Castro, Enrique A.,Aliaga, Margarita,Campodonico, Paola,Santos, Jose G.
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p. 8911 - 8916
(2007/10/03)
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- Carbamate synthesis from amines and dimethyl carbonate under ytterbium triflate catalysis
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A facile synthesis of carbamates from amines and dimethyl carbonate has been achieved using ytterbium triflate as catalyst.
- Curini, Massimo,Epifano, Francesco,Maltese, Federica,Rosati, Ornelio
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p. 4895 - 4897
(2007/10/03)
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- An environmentally benign access to carbamates and ureas
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Ureas were synthesized from methyl carbamates which were obtained by reaction of amines with dimethylcarbonate. Both reactions were catalyzed by γ-A12O3. (C) 2000 Elsevier Science Ltd.
- Vauthey,Valot,Gozzi,Fache,Lemaire
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p. 6347 - 6350
(2007/10/03)
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- New piperidine alkaloids from two ladybird beetles of the genus Calvia (Coccinellidae)
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The alkaloids of two coccinellid beetles, Calvia 14-guttata and C. 10- guttata have been studied. The major alkaloid of these two species is the new piperidinic cis-lactone 1a, for which the name calvine has been coined. The corresponding trans-lactone 1b
- Braekman, Jean-Claude,Charlier, Anne,Daloze, Desire,Heilporn, Sylvie,Pasteels, Jacques,Plasman, Valerie,Wang, Shaofang
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p. 1749 - 1755
(2007/10/03)
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- Palladium-Catalyzed Double and Single Carbonylations of β-Amino Alcohols. Selective Synthesis of Morpholine-2,3-diones and Oxazolidin-2-ones and Applications for Synthesis of α-Oxo Carboxylic Acids
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Catalytic cross double carbonylation of secondary amines and alcohols proceeds in the presence of [PdCl2(MeCN)2] and CuI under carbon monoxide (80 atm) and oxygen (5 atm). Catalytic intramolecular double carbonylation of β-amino alcohols gives morpholine-2,3-diones, which are excellent protecting compounds of amino alcohols and important precursors for biologically active nitrogen compounds. In contrast, catalytic single carbonylation of β-amino alcohols under a mixture (1 : 1) of carbon monoxide and oxygen (1.0 atm) proceeds to give oxazolidin-2-ones selectively. The reaction can be explained by assuming a mechanism which includes intramolecular nucleophilic attack of the hydroxy group of (hydroxyethyl)aminocarbonyl ligands on the CO ligand of the carbamoylpalladium(II) complexes, followed by reductive elimination to give morpholine-2,3-diones. In contrast, direct nucleophilic attack of the hydroxy group to the carbamoyl group affords oxazolidin-2-ones. As a common intermediate for the double and single carbonylations, carbamoylpalladium(II) complex has been isolated by the reaction of [PdCl2(PMe3)2] with β-amino alcohol under CO. The present double carbonylation of amino alcohols provides a novel and convenient method for synthesis of α-oxo carboxylic acids. Thus, the morpholine-2,3-diones obtained undergo reaction with Grignard reagents chemoselectively at the ester positions to give 2-substituted 2-hydroxymorpholin-3-ones, which undergo acid hydrolysis to give α-oxo carboxylic acids.
- Imada, Yasushi,Mitsue, Yo,Ike, Kazuo,Washizuka, Ken-Ichi,Murahashi, Shun-Ichi
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p. 2079 - 2090
(2007/10/03)
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- Carbamoyl complexes as a source of isocyanates or carbamyl chlorides
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Isocyanates or carbamyl chlorides have been prepared by reaction of carbamoyl complexes of nickel and palladium with CuCl2.Isocyanates are selectively produced from the carbamoyl complexes of primary amines, , (L=2,6-bis(diphenylphosphinomethyl) pyridine; R=C6H5, p-CH3C6H4, or p-ClC6H4)) and , whereas carbamoyl complexes of secondary amines, such as , afford carbamyl chloride.As expected, the reaction of the resulting isocyanates or carbamyl chlorides in situ with alcohols or amines produces carbamates or N,N'-substituted ureas, respectively.Key words: Carbamyl chloride; Carbamate; Carboxamide; Chloroformamide; Complex; Isocyanates; Palladium; Phosphine; Synthesis
- Giannoccaro, Potenzo,Tommasi, Immacolata,Aresta, Michele
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- Kinetics and Mechanism of the Reactions of Anilines and Secondary Alicyclic Amines with 2,4-Dinitrophenyl Methyl Carbonate
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The title reactions were subjected to a kinetic study in water at 25.0 deg C and ionic strength 0.2 mol dm-3 (KCl).The reactions are first order in both the substrate and the amine, without complications of acid-base catalysis.The Broensted-type plots obtained are linear for the reactions of anilines and nonlinear for those of alicyclic amines.The latter can be explained by the presence of a tetrahedral intermediate (T+/-) in the reaction path and a change in the rate determining step, but it is also compatible with a concerted process with a changing structure of the transition state.The linear Broensted plot is explained by a stepwise mechanism where the rate determining step is the decomposition of T+/- to products.Comparison with other Broensted plots indicates that the methoxy and alicyclic amino groups tend to destabilize T+/- kinetically (relative to methyl and pyridino) whereas the change of 2,4-dinitrophenylthio by 2,4-dinitrophenoxy as the leaving group renders T+/- more stable kinetically.
- Castro, Enrique A.,Ibanez, Fernando,Saitua, Ana M.,Santos, Jose G.
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p. 317 - 327
(2007/10/02)
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- Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines
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Electroreduction of nitriles gave the corresponding decyanated products when Zn was used as the material of cathode in aprotic solvent (DMF or MeCN) containing Et4NOTs as a supporting electrolyte. Alkylation of amines at the α-position was effectively achieved by cyanation of amines at the α-position, and α-alkylation of the resultant α-amino nitriles followed by the electroreductive decyanation.
- Shono, Tatsuya,Terauchi, Jun,Kitayama, Kenji,Takeshima, Yo-Ichiro,Masumura, Yoshihiro
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p. 8253 - 8262
(2007/10/02)
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- α-Haloalkyl Haloformates and Related Compounds 1. A Convenient Synthesis of Carbamates via Chloromethyl Carbamates
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The preparation of carbamates under mild conditions utilizing a new class of activated carbonates (containing chloromethyl function) is described.
- Patonay, Tamas,Patonay-Peli, Erzsebet,Mogyorodi, Ferenc
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p. 2865 - 2885
(2007/10/02)
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- Novel Synthesis of Carbamic Ester from Carbon Dioxide, Amine, and Ortho Ester
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Carbon dioxide reacted with aliphatic amines and ortho esters to form carbamic esters in good yields.The influence of different ortho esters on the carbamate synthetic reaction is described.In the case of orthocarbonates, carbamic esters were obtained in high yields.The reaction of carbon dioxide, amines, and ortho esters may involve a competitive reaction between the esterification of carbamic acid produced by a reaction of carbon dioxide with amine, and the alkylation of amine.
- Ishii, Shideru,Nakayama, Hidenobu,Yoshida, Yasuhiko,Yamashita, Tadataka
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p. 455 - 458
(2007/10/02)
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- 1,3-Dipolar Cycloadditions, 93. - The Astounding Reaction of Dimethyl 2,3-Dicyanofumarate with Diazomethane
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The reaction with excess of diazomethane furnished methyl 4-cyano-1-methylpyrazole-5- and -3-carboxylate (2 and 3) as well as the three N-methyl-1,2,3-triazolecarboxylic esters 4-6.A mechanistic study revealed a poly-step sequence.The initial formation of the pyrazoline 8 proceeded normal.Base catalysis effected an equilibration of trans- and cis-2-pyrazoline, 8(*)12, followed by a fragmentation into methyl 4-cyano-3-pyrazolecarboxylate (26) and methyl cyanoformate (32); a 4H-pyrazole is supposed to be the key intermediate.The final products mentioned above emerged from further reaction of 26 and 32 with diazomethane.
- Huisgen, Rolf,Mitra, Abhijit,Moran, Joaquin Rodriguez
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p. 159 - 170
(2007/10/02)
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- Palladium-catalysed Cross Double Carbonylation of Amines and Alcohols: Synthesis of Oxamates
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Cross double carbonylation of amines and alcohols in the presence of PdCl2(MeCN)2/CuI catalyst under CO and O2 at room temperature gives oxamates efficiently.
- Murahashi, Shun-Ichi,Mitsue, Yo,Ike, Kazuo
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p. 125 - 127
(2007/10/02)
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- THE ASTOUNDING REACTION OF DIAZOMETHANE WITH DIMETHYL 2,3-DICYANOFUMARATE
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The title reaction afforded the pyrazole derivatives 3 and 4 as well as the N-methyl-1,2,3-triazolecarboxylic esters 5 - 7.The poly-step sequence was clarified; the key intermediates are the 1-pyrazoline 18, the 2-pyrazoline 2, the 4H-pyrazole 12, the pyrazole 22, and methyl cyanoformate.
- Huisgen, Rolf,Mitra, Abhijit,Moran, Joaquin Rodriguez
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p. 2429 - 2436
(2007/10/02)
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- Improved Preparation of Meerwein's Ester and Structure of Neutral By-products: Pentamethyl 1,1,3,3,5-Cyclohexanepentacarboxylate and Methyl 1-Piperidinecarboxylate
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In a simplified procedure on a 10 mole scale, Meerwein's ester (2) is obtained from dimethyl malonate and formaldehyde in 48 - 52percent yield if the reaction time is extended and the disodium salt of 2 is isolated.Methyl 1-piperidinecarboxylate (7) and pentamethyl 1,1,3,3,5-cyclohexanepentacarboxylate (8) are formed as neutral by-products.The structure of the latter is confirmed by spectroscopic methods.The mechanism of formation of 8 is discussed.
- Quast, Helmut,Goerlach, Yvonne,Stawitz, Josef
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p. 1653 - 1658
(2007/10/02)
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- RAPID REDUCTIVE-CARBOXYLATION OF SECONDARY AMINES. ONE POT SYNTHESIS OF TERTIARY N-METHYLATED AMINES
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Various tertiary N-methylated amines were synthesized by using a new reductive-carboxylation approach.Secondary amines, on carboxylation with carbon dioxide under moderate reaction conditions, afforded their corresponding carbamate esters, which, on in situ lithium aluminum hydride reduction, gave desired tertiary N-methylated amines in high yield.
- Ram, Siya,Ehrenkaufer, Richard E.
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p. 5367 - 5370
(2007/10/02)
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- A CONVENIENT METHOD FOR THE CONVERSION OF AMINES TO CARBAMATES
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Treatment of primary or secondary amines with bis(trimethylsilyl)acetamide followed by addition of methyl, vinyl, or 2,2,2-trichloroethyl chloroformate provides a convenient method for the preparation of the corresponding carbamates.
- Raucher, Stanley,Jones, David S.
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p. 1025 - 1032
(2007/10/02)
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- 3-Alkoxycarbonyl-2-oxazolones and Their Homopolymers as Highly Preservable Amino-Protecting Reagents. tert-Butoxy-carbonylation and Benzyloxycarbonylation of Amino Groups
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Highly preservable amino protecting reagents derived from the 2-oxazolone moiety as a common activating mediator have been developed. 3-Alkoxycarbonyl-2-oxazolones serve as easily handled reagents for amino protection, including tert-butoxycarbonylation, benzyloxycarbonylation, p-methoxybenzyloxycarbonylation, methoxycarbonylation and ethoxycarbonylation.For example, high yield N-protection of α-amino acids has been smoothly performed by the use of 3-tert-butoxycarbonyl and 3-benzyloxycarbonyl-2-oxazolones in aqueous solution at room temperature.A series of homopolymers, poly(3-alkoxycarbonyl-2-oxazolone), is readily obtainable by radical-initiated chain reaction of the corresponding 4,5-unsubstituted oxazolone monomers (except for the tert-butoxy derivate, which failed to give polymeric compounds), and these were successfully used for amino protection as well.Use of the polymer reagents greatly simplifies the purification procedure, though a longer reaction time is required.Keywords - 3-alkoxycarbonyl-2-oxazolone; poly(2-alkoxycarbonyl-2-oxazolone); 3-tert-butoxycarbonyl-2-oxazolone; 3-benzyloxycarbonyl-2-oxazolone; amino protection
- Kunieda, Takehisa,Higuchi, Tsunehiko,Abe, Yoshihiro,Hirobe, Masaaki
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p. 2174 - 2181
(2007/10/02)
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- Electroorganic Chemistry. 46. A New Carbon-Carbon Bond Forming Reaction at the α-Position of Amines Utilizing Anodic Oxidation as a Key Step
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A new carbon-carbon bond forming reaction at the α-position of primary and secondary amines has been exploited.The method involves anodic oxidation of urethanes derived from the primary and secondary amines and subsequent acid-catalyzed reaction of the re
- Shono, Tatsuya,Matsumura, Yoshihiro,Tsubata, Kenji
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p. 1172 - 1176
(2007/10/02)
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- ADDITION D' AZIDES A DES OLEFINES TRISUBSTITUEES PAR DES GROUPEMENTS ELECTROATTRACTEURS
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The reaction of benzyl, methyl and phenyl azide, with olefins substituted by three electron-withdrawing groups, has been studied.This reaction gives in certain cases only one triazoline (single orientation of the cycloaddition).In other cases, a mixture o
- Ouali, Mohand Said,Vaultier, Michel,Carrie, Robert
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p. 1821 - 1828
(2007/10/02)
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- Kinetics of Hydrolysis and Aminolysis of 1-Methoxycarbonylpyridinium Ions
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Rate constants are reported for reactions of 1-methoxycarbonylpyridinium ions in aqueous solution with water, hydroxide ion, and primary and secondary amines.The water reaction is general base-catalysed; solvent isotope effects are reported.Both the water and hydroxide reactions proceed with rate-determining formation of tetrahedral intermediate. with the primary and secondary amines, either formation or breakdown of a tetrahedral intermediate is rate determining, depending upon the ring substituent.Structure-reactivity plots lead to estimates of relative leavig-group abilities, which are compared with others in the literature.Hydroxide-ion catalysed aminolysis is observed in some cases, and occurs by a concerted mechanism.
- Battye, Peter J.,Ihsan, Ekmel M.,Moodie, Roy B.
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p. 741 - 748
(2007/10/02)
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