- Pentacoordinated Carboxylate π-Allyl Nickel Complexes as Key Intermediates for the Ni-Catalyzed Direct Amination of Allylic Alcohols
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Direct amination of allylic alcohols with primary and secondary amines catalyzed by a system made of [Ni(1,5-cyclooctadiene)2] and 1,1′-bis(diphenylphosphino)ferrocene was effectively enhanced by adding nBu4NOAc and molecular sieves, affording the corresponding allyl amines in high yield with high monoallylation selectivity for primary amines and high regioselectivity for monosubstituted allylic alcohols. Such remarkable additive effects of nBu4NOAc were elucidated by isolating and characterizing some nickel complexes, manifesting the key role of a charge neutral pentacoordinated η3-allyl acetate complex in the present system, in contrast to usual cationic tetracoordinated complexes earlier reported in allylic substitution reactions.
- Kita, Yusuke,Sakaguchi, Hironobu,Hoshimoto, Yoichi,Nakauchi, Daisuke,Nakahara, Yasuhito,Carpentier, Jean-Fran?ois,Ogoshi, Sensuke,Mashima, Kazushi
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Read Online
- Fused ring compound and preparation method thereof
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The invention provides a fused ring compound and a preparation method thereof. In the method, precursor compounds A and B prepared under the conditions of triethylamine as a base, DMF as a solvent andpalladium acetate and triphenylphosphine as a catalyst react to generate a series of new fused ring compounds with a unique stereoselectivity. Compared with the conventional fused ring compound, thefused ring compound prepared by the invention has a more complicated structure, a mild reaction condition and a high reaction yield. The fused ring compound also shows a broader prospect of use in chemical production and clinical medicine.
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Paragraph 0106; 0110-0111
(2021/09/21)
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- Synthesis of functionalized indoles via palladium-catalyzed cyclization of N-(2-allylphenyl) benzamide: A method for synthesis of indomethacin precursor
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We developed an efficient method for synthesis of substituted N-benzoylindole via Pd(II)-catalyzed C-H functionalization of substituted N-(2-allylphenyl)benzamide. The reaction showed a broad substrate scope (including N-acetyl and N-Ts substrates) and substituted indoles were obtained in good to excellent yields. The most distinctive feature of this method lies in the high selectivity for N-benzoylindole over benzoxazine, and this is the first example of Pd(II)-catalyzed synthesis of substituted N-benzoylindole. Notably, this new method was applied for the synthesis of key intermediate of indomethacin.
- Chang, Zhe,Dong, Zheng,Ma, Tong,Zhang, Yu,Zhao, Depeng,Zhao, Heng
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supporting information
(2020/03/19)
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- Room Temperature Iron-Catalyzed Transfer Hydrogenation and Regioselective Deuteration of Carbon-Carbon Double Bonds
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An iron catalyst has been developed for the transfer hydrogenation of carbon-carbon multiple bonds. Using a well-defined β-diketiminate iron(II) precatalyst, a sacrificial amine and a borane, even simple, unactivated alkenes such as 1-hexene undergo hydrogenation within 1 h at room temperature. Tuning the reagent stoichiometry allows for semi- and complete hydrogenation of terminal alkynes. It is also possible to hydrogenate aminoalkenes and aminoalkynes without poisoning the catalyst through competitive amine ligation. Furthermore, by exploiting the separate protic and hydridic nature of the reagents, it is possible to regioselectively prepare monoisotopically labeled products. DFT calculations define a mechanism for the transfer hydrogenation of propene with nBuNH2 and HBpin that involves the initial formation of an iron(II)-hydride active species, 1,2-insertion of propene, and rate-limiting protonolysis of the resultant alkyl by the amine N-H bond. This mechanism is fully consistent with the selective deuteration studies, although the calculations also highlight alkene hydroboration and amine-borane dehydrocoupling as competitive processes. This was resolved by reassessing the nature of the active transfer hydrogenation agent: experimentally, a gel is observed in catalysis, and calculations suggest this can be formulated as an oligomeric species comprising H-bonded amine-borane adducts. Gel formation serves to reduce the effective concentrations of free HBpin and nBuNH2 and so disfavors both hydroboration and dehydrocoupling while allowing alkene migratory insertion (and hence transfer hydrogenation) to dominate.
- Espinal-Viguri, Maialen,Neale, Samuel E.,Coles, Nathan T.,MacGregor, Stuart A.,Webster, Ruth L.
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supporting information
p. 572 - 582
(2019/01/08)
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- Synthesis of Benzofuran and Indole Derivatives Catalyzed by Palladium on Carbon
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Benzofurans and indoles are key moieties in many natural products and pharmaceuticals. Herein, we describe a cheap and easy-to-execute strategy for the synthesis of benzofurans and indoles, employing Pd/C as the promoter. A variety of substituted allyl-anilines and allyl-phenols were converted into the desired products in good to excellent yields. Recycling of Pd/C was possible up to five cycles, keeping similar levels of reactivity.
- Savvidou, Anatoli,IoannisTzaras, Dimitrios,Koutoulogenis, Giorgos S.,Theodorou, Alexis,Kokotos, Christoforos G.
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supporting information
p. 3890 - 3897
(2019/06/27)
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- Indole compound and synthesizing and application methods thereof
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The invention relates to an indole compound and synthesizing and application methods thereof. The indole compound is prepared by selecting specific substituent groups. Experiments find that the indolecompound can achieve good inhibiting effects on prostatic cancer, good in drug-resistance-proofness and low in side effects when applied as an anti-cancer drug; besides, the synthesizing method of the indole compound comprises subjecting a compound with the structure shown as the formula (II), palladium acetate, benzoquinones and organic acids to reaction in solvent to obtain the indole compoundwith the structure shown as the formula (I). Experiment results show that the synthesizing method of the indole compound is low in requirements on substrate and high in product yield.
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Paragraph 0076-0079; 0093-0094; 0106-0107
(2019/10/22)
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- One-pot Construction of Difluorinated Pyrrolizidine and Indolizidine Scaffolds via Copper-Catalyzed Radical Cascade Annulation
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A convenient approach to the synthesis of diverse difluorinated nitrogen-containing polycycles via a copper-catalyzed radical cascade annulation of amine-containing olefins and ethyl bromodifluoroacetate was developed. Three new bonds, including a Csp3 ?CF2 and two C?N bonds, are forged simultaneously in this strategy. Through this strategy, a series of difluorinated pyrrolizidine and indolizidine derivatives have been conveniently synthesized in good yields. (Figure presented.).
- Wang, Xiaoyang,Li, Miao,Yang, Yanyan,Guo, Minjie,Tang, Xiangyang,Wang, Guangwei
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supporting information
p. 2151 - 2156
(2018/04/26)
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- A Simple, Broad-Scope Nickel(0) Precatalyst System for the Direct Amination of Allyl Alcohols
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The preparation of allylic amines is traditionally accomplished by reactions of amines with reactive electrophiles, such as allylic halides, sulfonates, or oxyphosphonium species; such methods involve hazardous reagents, generate stoichiometric waste streams, and often suffer from side reactions (such as overalkylation). We report here the first broad-scope nickel-catalysed direct amination of allyl alcohols: An inexpensive NiII/Zn couple enables the allylation of primary, secondary, and electron-deficient amines without the need for glove-box techniques. Under mild conditions, primary and secondary aliphatic amines react smoothly with a range of allyl alcohols, giving secondary and tertiary amines efficiently. This “totally catalytic” method can also be applied to electron-deficient nitrogen nucleophiles; the practicality of the process was demonstrated in an efficient, gram-scale preparation of the calcium antagonist drug substance flunarizine (Sibelium).
- Sweeney, Joseph B.,Ball, Anthony K.,Lawrence, Philippa A.,Sinclair, Mackenzie C.,Smith, Luke J.
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supporting information
p. 10202 - 10206
(2018/08/06)
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- Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes
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Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields. (Figure presented.).
- Theodorou, Alexis,Kokotos, Christoforos G.
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supporting information
p. 1577 - 1581
(2017/05/05)
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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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p. 1469 - 1473
(2016/09/19)
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- Palladium-Catalyzed Aerobic Intramolecular Aminoacetoxylation of Alkenes Enabled by Catalytic Nitrate
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A mild aerobic intramolecular aminoacetoxylation method for the synthesis of pyrrolidine and indoline derivatives was achieved using molecular oxygen as the oxidant. A catalytic NOx species acts as an electron transfer mediator to access a high-valent palladium intermediate as the presumed active oxidant.
- Li, Jiaming,Grubbs, Robert H.,Stoltz, Brian M.
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supporting information
p. 5449 - 5451
(2016/11/17)
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- Facet-Dependent Catalytic Activity of Palladium Nanocrystals in Tsuji-Trost Allylic Amination Reactions with Product Selectivity
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Pd nanocubes, cuboctahedra, and octahedra with good size control were used to catalyze C-N bond formation in the Tsuji-Trost allylic amination reaction of aniline. Nanocubes gave either monoallylaniline or diallylaniline depending on the amount of allyl bromide used, but the octahedra and cuboctahedra only gave mixtures of monoallylaniline and diallylaniline under the same reaction conditions. The Pd nanocubes were stable over multiple cycles of the reaction. The cubes and octahedra were demonstrated to catalyze the amination reaction by using a wide variety of substituted anilines, but the cubes were the best catalyst with consistently the highest efficiency, product yield, and product selectivity. This work demonstrates that the use of metal nanocrystals with proper facet control is important for catalyzing coupling reactions with product selectivity. Getting into shapes: Pd nanocubes, cuboctahedra, and octahedra with good size control are used to catalyze C-N bond formation in the Tsuji-Trost allylic amination reaction of aniline. The Pd nanocube catalyst gives good product selectivity, whereas the Pd octahedra and cuboctahedra catalysts yield mixtures of products under the same reaction conditions. Furthermore, Pd nanocubes are stable over multiple reaction cycles.
- Chanda, Kaushik,Rej, Sourav,Liu, Shu-Ya,Huang, Michael H.
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p. 1813 - 1817
(2015/06/23)
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- Copper-catalyzed radical cascade cyclization for the synthesis of phosphorated indolines
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A novel and convenient approach to the synthesis of various phosphorated indolines via a copper-catalyzed radical cascade cyclization reaction has been developed. The reaction employs cheap copper as the catalyst and K2S2O8 as the oxidant under mild conditions. Various alkenes and P-radical precursors are compatible with this transformation. Preliminary mechanistic studies reveal that the addition of the P-radical may initiate the reaction, and then oxidative cyclization may be achieved to afford the desired product. This journal is
- Zhang, Hong-Yu,Mao, Liu-Liang,Yang, Bin,Yang, Shang-Dong
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supporting information
p. 4101 - 4104
(2015/03/30)
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- Highly selective N-allylation of anilines under microwave irradiation
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An easy and rapid procedure for the preparation of a variety of mono- and bis-allylated anilines via the reaction of allyl bromide with a wide range of anilines under microwave irradiation is described. This approach allows use of mild conditions and short reaction times to give high selectivities and excellent yields.
- Liu, Meiyu,Wang, Xie,Sun, Xiaoliang,He, Wei
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p. 2711 - 2714
(2014/05/06)
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- Efficient copper-catalyzed direct intramolecular aminotrifluoromethylation of unactivated alkenes with diverse nitrogen-based nucleophiles
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A mild, convenient, and step-economical intramolecular aminotrifluoromethylation of unactivated alkenes with a variety of electronically distinct, nitrogen-based nucleophiles in the presence of a simple copper salt catalyst, in the absence of extra ligand
- Lin, Jin-Shun,Xiong, Ya-Ping,Ma, Can-Liang,Zhao, Li-Jiao,Tan, Bin,Liu, Xin-Yuan
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supporting information
p. 1332 - 1340
(2014/04/03)
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- Silica-functionalized CuI: An efficient and selective catalyst for N-benzylation, allylation, and alkylation of primary and secondary amines in water
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Silica-functionalized CuI has been reported as an efficient and selective catalyst for the selective mono-N- and N,N-dibenzylation, allylation, and alkylation of primary amines with benzylic, allylic, and alkyl halides using NaOH as base in aqueous medium. By changing the reaction temperature, mono- or di-benzylation, allylation, or alkylation could be achieved in good yield and selectivity. Secondary amines have also been benzylated, allylated, and alkylated under similar conditions. SiO2-CuI has been characterized by Fourier transform-infrared, atomic absorption spectrometry, thermalgravimetric analysis, X-ray diffraction, scanning electron microscopy, and transmission electron microscopy, and found to be highly selective and recyclable under the reaction conditions. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the following free supplemental resource(s): Full experimental and spectral details.] Copyright
- Shamim, Tahira,Kumar, Vineet,Paul, Satya
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p. 620 - 632
(2014/01/17)
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- Palladium-catalyzed selective aminoamidation and aminocyanation of alkenes using isonitrile as amide and cyanide sources
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A mild and efficient palladium-catalyzed intermolecular aminoamidation and aminocyanation reaction of alkenes with a broad substrate scope has been developed. This cyclization process provides a valuable synthetic tool for obtaining substituted indolines, tetrahydroisoquinolines and pyrrolidines in good to excellent yields. This journal is
- Jiang, Huanfeng,Gao, Hanling,Liu, Bifu,Wu, Wanqing
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supporting information
p. 15348 - 15351
(2015/01/08)
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- Promiscuity and selectivity in covalent enzyme inhibition: A systematic study of electrophilic fragments
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Covalent ligand-target interactions offer significant pharmacological advantages. However, off-target reactivity of the reactive groups, which usually have electrophilic properties, must be minimized, and the selectivity of irreversible inhibitors is a crucial requirement. We therefore performed a systematic study to determine the selectivity of several electrophilic groups that can be used as building blocks for covalently binding ligands. Six reactive groups with modulated electrophilicity were combined with 11 nonreactive moieties, resulting in a small combinatorial library of 72 fragment-like compounds. These compounds were screened against a group of 11 enzyme targets to assess their selectivity and their potential for promiscuous binding to proteins. The assay results showed a considerably lower degree of promiscuity than initially expected, even for those members of the screening collection that contain supposedly highly reactive electrophiles.
- J?st, Christian,Nitsche, Christoph,Scholz, Therese,Roux, Lionel,Klein, Christian D.
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supporting information
p. 7590 - 7599
(2014/12/11)
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- Synthesis of quinolines and fused pyridocoumarins from N-propargylanilines or propargylaminocoumarins by catalysis with gold nanoparticles supported on TiO2
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[5,6]-Fused pyridocoumarins are prepared under mild conditions in excellent yields through the activation of the triple bond of 6-propargylaminocoumarins by gold nanoparticles supported on TiO2. The analogous reaction of N-propargylanilines with Au/TiO2 or Au/Al2O3 resulted in the formation of quinolines.
- Symeonidis, Theodoros S.,Lykakis, Ioannis N.,Litinas, Konstantinos E.
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p. 4612 - 4616
(2013/06/26)
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- Preparation of N-arylamines from 2-oxo-7-azobicyclo[4.1.0]heptanes
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A wide range of N-phenylated secondary amines were prepared directly from 2-oxo-7-azobicyclo[4.1.0]heptanes using 4-nitrobenzoic acid as acid catalyst. The intermediate enol esters could also be isolated under similar conditions. A catalytic cycle is proposed.
- Barros, M. Teresa,Dey, Suvendu S.,Maycock, Christopher D.,Rodrigues, Paula
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supporting information; experimental part
p. 6263 - 6268
(2012/08/28)
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- A new entry to the phenanthridine ring system
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A new synthesis of phenanthridine derivatives having three-point diversity has been developed based on the sequential application of three-atom economic processes viz. aza-Claisen rearrangement, ring-closing enyne metathesis and Diels-Alder reaction as key steps. An unexpected isomerisation was observed during aza-Claisen rearrangement of N-allylanilines which may open up new opportunities in heterocyclic synthesis.
- Mondal, Poulomi,Thander, Latibuddin,Chattopadhyay, Shital K.
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p. 1328 - 1331
(2012/04/04)
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- Catalytic enantioselective alkene aminohalogenation/cyclization involving atom transfer
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Problem solved: The title reaction was used for the synthesis of chiral 2-bromo, chloro, and iodomethyl indolines and 2-iodomethyl pyrrolidines (see scheme). Stereocenter formation is believed to occur by enantioselective cis aminocupration and C-X bond formation is believed to occur by atom transfer. The ultility of the products as versatile synthetic intermediates was demonstrated, as was a radical cascade cyclization sequence. Copyright
- Bovino, Michael T.,Chemler, Sherry R.
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supporting information; scheme or table
p. 3923 - 3927
(2012/05/20)
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- An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis
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The synthesis of N-aryl, N-tosyl, and N-alkyl pyrrolines from allyl alcohols and amines has been developed. The reaction sequence includes a palladium-catalyzed allylation step in which non-manipulated allyl alcohol is used to generate the diallylated amine in good to excellent yield. An excess of allyl alcohol was necessary for efficient diallylation of the amine, where the excess alcohol could be recycled three times. For aryl and tosyl amines, Pd[P(OPh)3]4 was used and for benzyl and alkyl amines a catalytic system comprising Pd(OAc)2, PnBu3, and BEt3 was used. Both the electronic properties and the steric influence of the amine affected the efficiency of the allylation. The isolated diallylated amines were transformed into their corresponding pyrrolines by ring-closing metathesis catalyzed by (H2IMes)(PCy3)Cl 2RuCHPh in good to excellent yield. A one-pot reaction was developed in which aniline was transformed into the corresponding pyrroline without isolating the diallylated intermediate. This one-pot reaction was successfully scaled-up to 1 mL of aniline in which the N-phenyl pyrroline was isolated in 95% yield. The versatility of the reaction in which 3-methyl-1-phenyl pyrroline was prepared in two-steps was demonstrated.
- Sawadjoon, Supaporn,Samec, Joseph S. M.
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scheme or table
p. 2548 - 2554
(2011/05/04)
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- Palladium-catalyzed cyclization/cyclopropanation reaction for the synthesis of fused N-containing heterocycles
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Palladium-catalyzed cyclization/cyclopropanation can be used to convert a range of substituted cyclic N-aryl allyl/methallyl amines efficiently and selectively to the corresponding fused tetrahydropyridine/cyclopropane-fused isoquinoline derivatives via β
- Nandi, Sukla,Ray, Jayanta K.
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scheme or table
p. 6993 - 6997
(2010/02/27)
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- Facile access to bicyclic sultams with methyl 1-sulfonylcyclopropane-l- carboxylate moieties
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N-(2,3-Dibromopropyl)- and N-(3,4-dibromobutyl)(methoxycarbonyl) methanesulfanilides upon treatment with potassium carbonate in DMF furnish, methyl 3-aryl-2,2-dioxo-2thia-3-azabicyclo[n.1.0]alkane-1.-carboxylates in yields ranging from 54 to 84% (10 examples). The starting materials were obtained by sulfonylation of N-alkenylanilines with methyl (chlorosulfonyl) acetate and. subsequent bromination. For the N-alkenylanil.in.es (10 examples, 60-77% yield) an efficient new synthesis employing a 2-nitrophenylsulfonyl substituent as a protective as well as an activating group has been developed. The 4-methoxyphenyl (PMP) group could easily be removed, from, the sultam. nitrogen atom by treatment with cerium(IV) ammonium nitrate.
- Rassadin, Valentin A.,Tomashevskiy, Aleksandr A.,Sokolov, Viktor V.,Ringe, Arne,Magull, Joerg,De Meijere, Armin
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experimental part
p. 2635 - 2641
(2009/11/30)
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- Synthesis of highly substituted dibenzoazocine derivatives by the aza-Claisen rearrangement and intramolecular Heck reaction via 8-exo-trig mode of cyclization
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The synthesis of highly substituted dibenzo-azocine systems is still lacking. An efficient synthetic protocol utilizing the sequential aromatic aza-Claisen rearrangement followed by the implementation of the intramolecular Heck reaction as a key step has been developed for the synthesis of various dibenzo-azocine derivatives of biological relevance.
- Majumdar,Chattopadhyay, Buddhadeb,Samanta, Srikanta
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scheme or table
p. 3178 - 3181
(2009/08/07)
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- Direct use of allylic alcohols for platinum-catalyzed monoallylation of amines
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A new direct catalytic amination of allylic alcohols promoted by the combination of platinum and a large bite-angle ligand DPEphos was developed in which the allylic alcohol was effectively converted to a π-allylplatinum intermediate without the use of an activating reagent. The use of the DPEphos ligand was essential for obtaining high catalyst activity and high monoallylation selectivity of primary amines, allowing the formation of a variety of monoallylation products in good to excellent yield.
- Utsunomiya, Masaru,Miyamoto, Yoshiki,Lpposhi, Junji,Ohshima, Takashi,Mashima, Kazushi
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p. 3371 - 3374
(2008/02/12)
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- Pd(II)-catalyzed enantioselective oxidative tandem cyclization reactions. Synthesis of indolines through C-N and C-C bond formation
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We have developed an efficient Pd(II)-catalyzed enantioselective oxidative tandem cyclization strategy using molecular oxygen as a green oxidant for the double 5-exo-trig cyclizations of N-(2-allylaryl) amides to afford a variety of indolines in good yiel
- Yip, Kai-Tai,Yang, Min,Law, Ka-Lun,Zhu, Nian-Yong,Yang, Dan
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p. 3130 - 3131
(2007/10/03)
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- Novel strategies for the solid phase synthesis of substituted indolines and indoles
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Using a polymer-bound selenenyl bromide resin, o-allyl and o-prenyl anilines were cycloaded to afford a series of solid-supported indoline and indole scaffolds. These scaffolds were then functionalized and cleaved via four distinct methods, namely traceless reduction, radical cyclization, radical rearrangement, and oxidative elimination, to afford 2-methyl indolines, polycyclic indolines, 2-methyl indoles, and 2-propenyl indolines, respectively. A number of small combinatorial libraries of compounds reminiscent of certain designed ligands of biological interest were constructed demonstrating the potential utility of the developed methodology to chemical biology studies and the drug discovery process.
- Nicolaou,Roecker,Hughes, Robert,Van Summeren, Ruben,Pfefferkorn, Jeffrey A.,Winssinger, Nicolas
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p. 465 - 476
(2007/10/03)
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- Indium-mediated barbier reactions of azides: A facile synthesis of N-allylamine derivatives
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N-Allylic amines are conveniently prepared in high yields by the reaction of azides with allylindium reagents in the presence of sodium iodide in DMF at ambient temperature.
- Yadav,Madhuri,Reddy,Reddy, G. S. Kiran Kumar,Sabitha
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p. 2771 - 2777
(2007/10/03)
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- Direct palladium-catalyzed selective monoallylation of anilines using allylic alcohols
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N-Allylation of anilines using allylic alcohols directly to give monoallylic anilines selectively in high yields has been realized by employing palladium acetate-triphenylphosphine as the catalyst. Palladium-catalyzed one-pot cyclization of 2-aminophenols with 2-butene-1,4-diol leads to 3,4-dihydro-2-vinyl-2H-1,4-benzoxazines. (C) 2000 Elsevier Science Ltd.
- Yang,Yu,Tsai
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p. 7097 - 7100
(2007/10/03)
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- Solid phase synthesis of aryl and heteroaryl amines using the Curtius rearrangement
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An efficient method for the solid phase synthesis of secondary aryl amines and heteroaryl amines was developed. The key step was the formation of aryl or heteroaryl carbamates using the Curtius rearrangement of aryl carboxylic acids with Wang resin as a trapping hydroxyl group. N-alkylation reactions of resin-bound carbamates under the Mitsunobu condition or using sodium hydride gave secondary aryl or heteroaryl amines in good yields. The developed method can be applied in the preparation of libraries containing aryl and heteroaryl amine structures as a pharmacophore.
- Sunami, Satoshi,Sagara, Takeshi,Ohkubo, Mitsuru,Morishima, Hajime
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p. 1721 - 1724
(2007/10/03)
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- Zinc Mediated Allylation of Azides: A Novel Method for the High Yield Preparation of N-Allylamines
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A quick and efficient approach for mono N-allylamines has been developed by the reaction of allyl zinc reagent with alkyl and aryl azides in DMF. - Keywords: azides; zinc; DMF; allylamine
- Kumar, H. M. Samapath,Anjaneyulu, S.,Reddy, B. V. Subba,Yadav, J. S.
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p. 551 - 552
(2007/10/03)
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- Palladium-catalyzed N-allylation of anilines by direct use of allyl alcohols in the presence of titanium(IV) isopropoxide
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The direct activation of C-O bonds in allyl alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium(IV) isopropoxide and 4A molecular sieves. N-Allylation of anilines to give mono- and diallylanilines using allyl alcohols directly has been realized by employing palladium catalysts.
- Yang, Shyh-Chyun,Chung, Wen-Hung
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p. 953 - 956
(2007/10/03)
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- An efficient palladium-catalyzed route to N-allylanilines by the direct use of allyl alcohols
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The direct activation of C-O bonds in allyl alcohols by palladium complexes has been accelerated by carrying out the reactions in the presence of titanium(IV) isopropoxide and molecular sieves (4A). N-Allylation of anilines to give mono- and diallylanilines directly using allyl alcohols has been realized by employing palladium catalysts.
- Yang, Shyh-Chyun,Hung, Chung-Wei
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p. 1747 - 1752
(2007/10/03)
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- Direct and selective N-monoalkynylation and N-monoalkenylation of anilines with alky(e)nyl methanesulfonates using methylmagnesium bromide as a base
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Several anilines were directly N-monoalkynylated and N-monoalkenylated with alkynyl methanesulfonates and alkenyl methanesulfonates, respectively, using methylmagnesium bromide as a base in good yields with high selectivities.
- Yoshida, Yoshihiro,Tanabe, Yoo
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p. 533 - 535
(2007/10/03)
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- 1H-INDAZOLES AS SYNTHETIC AUXILIARIES FOR THE SYNTHESIS OF SECONDARY AROMATIC AMINES
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Methodology of alkylation of aromatic amines using 1H-indazoles as synthetic auxiliares is reported.
- Saladino, Raffaele,Crestini, Claudia,Nicoletti, Rosario
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p. 567 - 574
(2007/10/02)
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- The Stereochemistry of Organometallic Compounds. XL. Rhodium-Catalysed Reactions of Hydrogen and Carbon Monoxide with Alkenylanilines
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Rhodium-catalysed reactions of o- or p-cyano-N-allylanilines with H2/CO give N-arylpyrrolidine aldehydes resulting from a double hydroformylation sequence.In contrast reactions of o- or p-methyl-N-allylanilines or N-allylaniline itself with H2/CO give 'dimeric' compounds resulting from self-condensation reactions of an initially formed hydroformylation product together with varying amounts of the double hydroformylation product.Similar reactions of o-cyano-N-but-3-enylanilines give low yields of double hydroformylation products and major products arising from hydrogenation or cross coupling of intermediate enamines.The structure of one of these products, N-2-cyanophenyl-5-(N'-2-cyanophenyl-3-methylpyrrolidin-2-yl)-1,2,3,4-tetrahydropyridine (17) (IUPAC name: 2--1,2,3,4-tetrahydropyridin-1-yl>benzonitrile) was confirmed by an X-ray single-crystal structure determination.
- Anastasiou, Despina,Campi, Eva M.,Chaouk, Hassan,Fallon, Gary D.,Jackson, W. Roy,et al.
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p. 1043 - 1060
(2007/10/02)
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- Catalytic aminomercuration of olefins in a tandem aminomercuration-deoxymercuration; one-step synthesis of secondary n-arylallylamines from allylalcohols
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Allyl alcohols react with primary aromatic amines and stoichiometric amounts of mercury(II) tetrafluoroborate to give mixtures of mono- and diallyl anilines. However, the use of the tandem aminomercuration-deoxymercuration promoted by catalytic mercury(II) tetrafluoroborate allows to perform regiospecifically the monoallylation reaction with very high yields. A mechanism is proposed to account for the observed results.
- Barluenga, Jose,Perez-Prieto, Julia,Asensio, Gregorio
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p. 2453 - 2460
(2007/10/02)
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