- Selectively substituted thiophenes and indoles by a tandem palladium-catalyzed multicomponent reaction
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A variety of di- and trisubstituted thiophenes were synthesized by a one-pot palladium-catalyzed ortho-alkylation sequence terminated by either Heck or C-H coupling. Initial results toward the functionalization of indoles are also presented.
- Mitsudo, Koichi,Thansandote, Praew,Wilhelm, Thorsten,Mariampillai, Brian,Lautens, Mark
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Read Online
- A simple, two-step synthesis of 3-iodoindoles
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2-Halo-anilines, protected as the corresponding sulfonamides or carbamates, can be converted very efficiently into 3-iodoindoles by sequential Sonogashira coupling with a 1-alkyne and 5-endo-dig iodocyclisation. Azaindoles can also be obtained using this methodology.
- Amjad, Muhammad,Knight, David W.
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Read Online
- Cobalt-Catalyzed Hydroalkynylation of Vinylaziridines
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Transition metal-catalyzed hydroalkynylation reactions are efficient transformations allowing the straightforward formation of functionalized alkynes. Therein, we disclose the cobalt-catalyzed hydroalkynylation of vinylaziridines giving rise to both linea
- Biletskyi, Bohdan,Kong, Lingyu,Tenaglia, Alphonse,Clavier, Hervé
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supporting information
p. 2578 - 2585
(2021/03/18)
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- Asymmetric Dearomatization of Indole by Palladium/PC-Phos-Catalyzed Dynamic Kinetic Transformation
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A palladium-catalyzed intermolecular dynamic kinetic asymmetric dearomatization of 3-arylindoles with internal alkynes was developed with the use of achiral Xantphos and chiral sulfinamide phosphine ligand (PC-Phos) as the co-ligands. This method could deliver various spiro[indene-1,3′-indole] compounds in good yields (up to 95 % yield) with up to 98 % ee. The salient features of the transformation include the use of readily available substrates, ease of scale-up and the versatile functionalization of the products. The mechanistic experiments gave some insights on active intermediates.
- Cheng, Jie,Chu, Haoke,Guo, Yin-Long,Yang, Junfeng,Zhang, Junliang
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supporting information
p. 21991 - 21996
(2020/10/02)
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- Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
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Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
- Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
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- Disulfide-Catalyzed Iodination of Electron-Rich Aromatic Compounds
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Herein, a disulfide-catalyzed electrophilic iodination of aromatic compounds using 1,3-diiodo-5,5-dimethylhydantoin (DIH) has been developed. The disulfide activates DIH as a Lewis base to promote the iodination reaction in acetonitrile under mild conditions. This system is applicable to a wide range of electron-rich aromatic compounds, including acetanilide, anisole, imidazole, and pyrazole derivatives.
- Iida, Keisuke,Ishida, Shunsuke,Watanabe, Takamichi,Arai, Takayoshi
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p. 7411 - 7417
(2019/06/18)
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- Enantioselective Synthesis of Cyclohepta[ b]indoles via Pd-Catalyzed Cyclopropane C(sp3)-H Activation as a Key Step
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An enantioselective synthesis of functionalized cyclohepta[b]indoles via Pd-catalyzed cyclopropane C-H activation followed by olefination and indole-vinylcyclopropane rearrangement is reported. The design of the chiral cyclopropane precursor was such that both enantiomeric cyclohepta[b]indoles were accessed from a single compound exhibiting a "hidden" symmetry plane. The scope of the method was demonstrated by varying the substituents on the cyclopropane as well as on the heterocycle itself.
- H?fner, Maximilian,Sokolenko, Yevhenii M.,Gamerdinger, Paul,Stempel, Erik,Gaich, Tanja
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supporting information
p. 7370 - 7374
(2019/10/08)
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- H-bonding vs Protonation of Alkynes in Regioselective Hydroamination Reactions: A Glimpse into the Reactivity of Arylogous Ynolethers and Ynamines
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In this paper is described the competition and transition between hydrogen bonding and protonation of alkynes connected, on one side, to various aromatic rings and to chiral amino ester appendages on the other side. While the first mode of activation indu
- Abe, Masahiro,Jean, Alexandre,Blanchet, Jér?me,Rouden, Jacques,Maddaluno, Jacques,De Paolis, Micha?l
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p. 15448 - 15475
(2019/11/29)
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- Transition-Metal-Free Decarboxylative Iodination: New Routes for Decarboxylative Oxidative Cross-Couplings
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Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional molecules, and efficient methods for their synthesis from chemical feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I2. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined. Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I2 as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.
- Perry, Gregory J. P.,Quibell, Jacob M.,Panigrahi, Adyasha,Larrosa, Igor
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supporting information
p. 11527 - 11536
(2017/08/30)
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- Pyrimidine derivatives Anaplastic lymphoma kinase inhibitors
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The invention belongs to the field of a medical technology and specifically relates to a pyrimidine derivative type anaplastic lymphoma kinase inhibitor as shown in the general formula (I) or its stereisomer, or its pharmaceutically acceptable salt, ester or solvate, wherein R1, R2, R3, R4, R5 and A ring are as defined in the specification. The invention also relates to a preparation method of the compounds, a pharmaceutic preparation and a pharmaceutical composition containing the compounds and an application of the compound or its stereisomer, or its pharmaceutically acceptable salt, ester or solvate in the preparation of medicines for treating and/or preventing diseases related to anaplastic lymphoma kinase-mediated cancer.
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Paragraph 0260-0262
(2017/07/23)
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- A new protocol for nickel-catalysed regio- and stereoselective hydrocyanation of allenes
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Regio- and stereoselective hydrocyanation under nickel catalysis is described. This report shows that allenyl C-C double bonds are discriminated and converted to the corresponding carbonitriles as a single product. The key functionalities for achieving high regio- and stereocontrol are aryl and cyclopropyl groups in the substrates. This journal is
- Arai, Shigeru,Hori, Hiroto,Amako, Yuka,Nishida, Atsushi
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supporting information
p. 7493 - 7496
(2015/05/04)
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- Masuda borylation-Suzuki coupling (MBSC) sequence of vinylhalides and its application in a one-pot synthesis of 3,4-biarylpyrazoles
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The Masuda borylation-Suzuki coupling (MBSC) sequence was successfully extended to the challenging coupling of vinylhalides with various (hetero)arylhalides using sterically hindered phosphane ligands. Starting from (hetero)arylhalides and α-bromocinnamaldehyde, the sequentially Pd-catalyzed process selectively furnishes α,β-substituted cinnamaldehydes without affecting the reactivity of the Michael system. These intermediates were implemented as entries into a novel synthesis of 3,4-diaryl 1H-pyrazoles in the fashion of a three-step one-pot procedure consisting of a Masuda borylation-Suzuki coupling and subsequent Michael addition- cyclocondensation-elimination sequence. The Royal Society of Chemistry.
- Tasch, Boris O. A.,Bensch, Lisa,Antovic, Dragutin,Müller, Thomas J. J.
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supporting information
p. 6113 - 6118
(2013/09/12)
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- One-pot synthesis of camalexins and 3,3′-biindoles by the Masuda borylation-Suzuki arylation (MBSA) sequence
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The Masuda borylation/Suzuki arylation (MBSA) sequence starting from N-protected 3-iodoindoles has successfully been extended to the coupling of five-membered heterocycles and indoles in the arylation step, which could not be achieved with previously developed MBSA methods. By this approach the one-pot nature of the method as well as the use of a simple catalyst system has been retained. The applicability of the method has been demonstrated by the facile synthesis of camalexins and 3,3′-biindoles, compounds of special interest due to their pronounced antifungal, antimicrobial and cytotoxic activities. The Masuda borylation/Suzuki arylation sequence furnishes in a concise one-pot manner camalexins and 3,3′-biindoles, compounds that show pronounced antifungal, antimicrobial, and cytotoxic activities. Copyright
- Tasch, Boris O. A.,Antovic, Dragutin,Merkul, Eugen,Mueller, Thomas J. J.
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p. 4564 - 4569
(2013/07/26)
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- A palladium-catalyzed domino reaction as key step for the synthesis of functionalized aromatic amino acids
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A variety of substituted aromatic systems are synthesized by the Catellani reaction. These are used as precursors for novel amino acids with a basic side chain. Georg Thieme Verlag Stuttgart New York.
- Stark, Tina,Suhartono, Marcel,G?bel, Michael W.,Lautens, Mark
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p. 2730 - 2734
(2014/01/06)
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- Domino C-H functionalization reactions of gem-dibromoolefins: Synthesis of N-fused benzo[c]carbazoles
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A palladium-catalyzed domino transformation of gem-dibromoolefins leading to novel polycyclic benzo[c]carbazoles is described. A unique feature of the current reaction is the participation of both bromides in C-H functionalization processes. Mechanistic studies were conducted to ascertain the sequence of reaction events, and the results indicate that the (Z)-bromide likely reacts in preference to the (E)-bromide.
- Huang, Richard Y.,Franke, Patrick T.,Nicolaus, Norman,Lautens, Mark
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supporting information
p. 4395 - 4402
(2013/06/27)
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- Synthesis of optically active homotryptophan and its oxygen and sulfur analogues
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d-Homotryptophan and its sulfur analogue have been synthesized by Sonogashira coupling between 3-iodoheteroarenes and ethynyloxazolidine followed by reduction of triple bond and oxidation of alcohol to acid. l-Homotryptophan and its oxygen analogue have b
- Goswami, Koushik,Paul, Sibasish,Bugde, Sandesh T.,Sinha, Surajit
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p. 280 - 286
(2012/01/05)
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- Mild synthetic approach to novel indole-1-carbinols and preliminary evaluation of their cytotoxicity in hepatocarcinoma cells
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A mild and versatile method for the synthesis of some novel indole-1-carbinols has been developed via one-pot reaction of indoles and paraformaldehyde in the presence of an excess of CaO, MgO, ZnO or TiO 2. The solvent-free reaction provided all the indole derivatives in moderate to good yields and short reaction times. Moreover, the effect of some selected indole-1-carbinols on cell proliferation of the hepatoma cell line FaO was evaluated.
- Zedda, Gloria,Simbula, Gabriella,Begala, Michela,Pibiri, Monica,Floris, Costantino,Casu, Mariano,Casu, Laura,Tocco, Graziella
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p. 195 - 202
(2012/06/04)
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- An acid-promoted novel skeletal rearrangement initiated by intramolecular ipso-Friedel-Crafts-type addition to 3-alkylidene indolenium cations
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An acid-promoted novel skeletal rearrangement is described. Using trifluoroacetic acid as the acid promoter, an intramolecular ipso-Friedel-Crafts-type addition of phenols to 3-alkylidene indolenium cations, formation of iminium cations through rearomatization of the spirocyclohexadienone units, and intramolecular Pictet-Spengler reaction proceeded sequentially, producing tricyclic indole derivatives.
- Yokosaka, Takuya,Nemoto, Tetsuhiro,Hamada, Yasumasa
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p. 5431 - 5433
(2012/07/03)
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- Efficient synthesis of maleimides and carbazoles via Zn(OTf) 2-catalyzed tandem annulations of Lsonitriles and allenic esters
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Lewis acid Zn(OTf)2-catalyzed tandem annulations of isonitriles and allenic esters which lead to efficient and flexible syntheses of a range of biologically significant maleimides and carbazoles and related compounds are reported. A mechanistic rationale is proposed to account for the observed reactivity.
- Li, Yuanzhen,Zou, Haixia,Gong, Jianxian,Xiang, Jing,Luo, Tuoping,Quan, Junmin,Wang, Guoxin,Yang, Zhen
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p. 4057 - 4060
(2008/02/11)
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- TREATMENT OF PROTEIN FOLDING DISORDERS
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In certain embodiments, the invention is directed to a method for treating a protein folding disorder such as Alzheimer's disease, dementia, Parkinson's disease, Huntington's disease and prion-based spongiform encephalopathy. The method comprises the administration to a subject of a compound of the formula (I) wherein A and B are independently a mono- or bicyclic aromatic group or heteroaromatic cyclic group. In preferred embodiments, the compounds are bis-indole compounds.
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Page/Page column 99; 108
(2010/11/25)
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- Hydroboration and Suzuki-Miyaura coupling reactions with the electronically modulated variant of an ynamine: The synthesis of (E)-β-arylenamides
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The first hydroboration of an 1-alkynylamide - the electronically modulated variant of an ynamine - is described. This hydroboration in combination with a Suzuki-Miyaura cross-coupling reaction with aryl bromides or aryl iodides allows a flexible synthesis of (E)-β-arylenamides and 3-(2'-amidovinyl)indoles with high degree of molecular diversity. (C) 2000 Elsevier Science Ltd.
- Witulski, Bernhard,Buschmann, Nicole,Bergstr??er, Uwe
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p. 8473 - 8480
(2007/10/03)
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