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  1. Article: [No title information]

    Chellappan, Sheela Kochuparambil / Haberhauer, Gebhard / Feuerbacher, Sven / Rominger, Frank / Oeser, Thomas / Gleiter, Rolf

    Synthesis

    3022  Volume 2003, Issue 03

    Abstract: The reaction of TERT-butyl acetate (6) with 1,4-dibromobut-2-yne (1) in the presence of LDA yielded 1,6-di(TERT-butyl)cyclodeca-3,8-diyne-1,6-dicarboxylate (8). The 1,6-di(TERT-butyl) groups of 8 were transferred to bis(hydroxymethyl) (5), bis( ... ...

    Abstract The reaction of TERT-butyl acetate (6) with 1,4-dibromobut-2-yne (1) in the presence of LDA yielded 1,6-di(TERT-butyl)cyclodeca-3,8-diyne-1,6-dicarboxylate (8). The 1,6-di(TERT-butyl) groups of 8 were transferred to bis(hydroxymethyl) (5), bis(bromomethyl) (13), bis(cyanomethyl) (14), dicarbaldehyde (15) and bis(methoxyvinyl) (16) groups. In case of 13 the two diastereomers [CIS(a,e), TRANS(a,a)] were separated. From 13(A,E) and 14(A,A) we were able to obtain detailed structural parameters by means of X-ray crystallography. By means of temperature dependent NMR spectroscopy of 14(A,A) we estimated the activation energy for the chair-boat conversion to be 10.5 kcal/mol.
    Keywords aldehydes ; alkynes ; condensations ; cyclizations ; esters
    Language English
    Publishing date 30228
    Publishing place Stuttgart ; New York
    Document type Article
    ZDB-ID 2033062-5
    ISSN 1437-210X ; 0039-7881
    ISSN (online) 1437-210X
    ISSN 0039-7881
    DOI 10.1055/s-2003-37347
    Database Thieme publisher's database

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  2. Article ; Online: Solvent-Controlled Racemic Resolution of

    Wagner, Philippe / Rominger, Frank / Oeser, Thomas / Mastalerz, Michael

    The Journal of organic chemistry

    2020  Volume 85, Issue 5, Page(s) 3981–3989

    Abstract: ... A ... ...

    Abstract A racemic
    Language English
    Publishing date 2020-02-10
    Publishing country United States
    Document type Journal Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.9b03410
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 4473: Show issues Location:
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  3. Article ; Online: A Symmetrically π-Expanded Carbazole Incorporating Fluoranthene Moieties.

    Vogel, Alexander / Schreyer, Till / Bergner, John / Rominger, Frank / Oeser, Thomas / Kivala, Milan

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2022  Volume 28, Issue 67, Page(s) e202201424

    Abstract: A novel doubly cyclopentannulated carbazole which is accessible through a successive π-expansion of di(1-naphthylamine) is disclosed. The carbazole moiety is generated in the final step through intramolecular oxidative coupling. The π-expansion of ... ...

    Abstract A novel doubly cyclopentannulated carbazole which is accessible through a successive π-expansion of di(1-naphthylamine) is disclosed. The carbazole moiety is generated in the final step through intramolecular oxidative coupling. The π-expansion of carbazole resulted in strongly altered optoelectronic and electrochemical properties. The solid-state structure features an interesting packing motif with alternating face-to-face π⋅⋅⋅π and edge-to-face C-H⋅⋅⋅π interactions. The experimental findings were corroborated by theoretical calculations.
    Language English
    Publishing date 2022-10-05
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202201424
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  4. Article ; Online: Cascade Reactions of Aryl-Substituted Terminal Alkynes Involving in Situ-Generated α-Imino Gold Carbenes.

    Sun, Qiaoying / Hüßler, Christopher / Kahle, Justin / Mackenroth, Alexandra V / Rudolph, Matthias / Krämer, Petra / Oeser, Thomas / Hashmi, A Stephen K

    Angewandte Chemie (International ed. in English)

    2023  Volume 63, Issue 5, Page(s) e202313738

    Abstract: An efficient, highly selective and divergent synthetic method to construct 2-substituted indoles and aryl-annulated carbazoles via the intermolecular generation of α-imino gold carbenes from terminal alkynes or diynes in combination with sulfilimines is ... ...

    Abstract An efficient, highly selective and divergent synthetic method to construct 2-substituted indoles and aryl-annulated carbazoles via the intermolecular generation of α-imino gold carbenes from terminal alkynes or diynes in combination with sulfilimines is disclosed. Importantly, the tandem reaction is proposed to proceed through an intermolecular gold carbene generation/C-H annulation followed by the activation of a second alkyne leading to 6-endo-dig cyclization, which is significantly different from previous dual activation or 1,6-carbene shift approaches for diyne systems. In the case of ortho-alkynylaniline as starting material, an unexpected regioselective formation of the indole moiety via the intermolecular path, instead of intramolecular hydroamination was discovered. This reactivity paved the way for a one-pot synthesis of the 11H-indolo [3,2-c] quinoline scaffold by exploiting the formed amino indole for a subsequent Pictet-Spengler reaction with aldehydes. The photophysical properties of the carbazoles indicated good violet-blue emission with quantum yields up to 40 %.
    Language English
    Publishing date 2023-12-21
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202313738
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Gold(I)-Catalyzed Intramolecular 7-endo-dig Cyclization of Triene-Yne Systems: New Access towards Azulenothiophenes.

    Eshagh Saatlo, Rebeka / Oczlon, Julian / Wunsch, Jonas F / Rudolph, Matthias / Rominger, Frank / Oeser, Thomas / Shiri, Farshad / Ariafard, Alireza / Hashmi, A Stephen K

    Angewandte Chemie (International ed. in English)

    2024  , Page(s) e202402481

    Abstract: We report the direct synthesis of new azulene derivatives through gold-catalyzed cyclization reactions. A five-membered ring as backbone in the applied triene-yne substrates turned out to be crucial to induce the 7-endo-dig cyclization mode necessary to ... ...

    Abstract We report the direct synthesis of new azulene derivatives through gold-catalyzed cyclization reactions. A five-membered ring as backbone in the applied triene-yne substrates turned out to be crucial to induce the 7-endo-dig cyclization mode necessary to trigger azulene formation. The obtained targets are of high interest due to their potential applications in different fields, like organic materials, medicine or cosmetics. UV/Vis spectra and cyclic voltammetry were measured, based on these the electronic properties were determined. Short two or three step sequences towards the applied starting materials make this approach synthetically highly attractive.
    Language English
    Publishing date 2024-03-26
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202402481
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  6. Article ; Online: Soluble Congeners of Prior Insoluble Shape-Persistent Imine Cages.

    Holsten, Mattes / Feierabend, Sarah / Elbert, Sven M / Rominger, Frank / Oeser, Thomas / Mastalerz, Michael

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 27, Issue 36, Page(s) 9383–9390

    Abstract: One of the most applied reaction types to synthesize shape-persistent organic cage compounds is the imine condensation reaction and it is assumed that the formed cages are thermodynamically controlled products due to the reversibility of the imine ... ...

    Abstract One of the most applied reaction types to synthesize shape-persistent organic cage compounds is the imine condensation reaction and it is assumed that the formed cages are thermodynamically controlled products due to the reversibility of the imine condensation. However, most of the synthesized imine cages reported are formed as precipitate from the reaction mixture and therefore rather may be kinetically controlled products. There are even examples in literature, where resulting cages are not soluble at all in common organic solvents to characterize or study their formation by NMR spectroscopy in solution. Here, a triptycene triamine containing three solubilizing n-hexyloxy chains has been used to synthesize soluble congeners of prior insoluble cages. This allowed us to study the formation as well as the reversibility of cage formation in solution by investigating exchange of building blocks between the cages and deuterated derivatives thereof.
    Language English
    Publishing date 2021-05-24
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202100666
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  7. Article ; Online: Fully Bridged Triphenylamines Comprising Five- and Seven-Membered Rings.

    Michalsky, Ina / Gensch, Viktoria / Walla, Christian / Hoffmann, Marvin / Rominger, Frank / Oeser, Thomas / Tegeder, Petra / Dreuw, Andreas / Kivala, Milan

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2022  Volume 28, Issue 34, Page(s) e202200326

    Abstract: A family of fully bridged triphenylamines with embedded 5- and 7-membered rings is presented. The compounds are potent electron donors capable to undergo donor/acceptor interactions with strong cyano-based acceptors both in the solid state and solution. ... ...

    Abstract A family of fully bridged triphenylamines with embedded 5- and 7-membered rings is presented. The compounds are potent electron donors capable to undergo donor/acceptor interactions with strong cyano-based acceptors both in the solid state and solution. These interactions were evaluated by IR and UV/vis spectroscopy as well as X-ray crystallography. The vinylene-bridged compound was oxidized to the corresponding 1,2-diketone which readily underwent acid-catalyzed condensation with selected 1,2-phenylenediamines. The resulting π-extended quinoxaline derivatives represent valuable building blocks for the development of functional chromophores upon appropriate functionalization.
    Language English
    Publishing date 2022-05-09
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202200326
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  8. Article ; Online: Gold(I)-Catalyzed Cycloisomerization of 3-Alkoxyl-1,6-diynes: A Facile Access to Bicyclo[2.2.1]hept-5-en-2-ones.

    Hu, Chao / Wang, Tao / Rudolph, Matthias / Oeser, Thomas / Asiri, Abdullah M / Hashmi, A Stephen K

    Angewandte Chemie (International ed. in English)

    2020  Volume 59, Issue 22, Page(s) 8522–8526

    Abstract: A novel gold-catalyzed cycloisomerization of 1,6-diynes was achieved, providing an atom-economic approach to a diverse set of bicyclo[2.2.1]hept-5-en-2-ones in moderate to good yields. With unsymmetrical starting materials with two different internal ... ...

    Abstract A novel gold-catalyzed cycloisomerization of 1,6-diynes was achieved, providing an atom-economic approach to a diverse set of bicyclo[2.2.1]hept-5-en-2-ones in moderate to good yields. With unsymmetrical starting materials with two different internal alkynyl substituents, to some extent, the regioselectivity could be controlled by both electronic and steric factors. This unprecedented reactivity pattern may inspire new and unconventional strategies for the preparation of bridged ring systems.
    Language English
    Publishing date 2020-03-24
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201914284
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  9. Article ; Online: TIPS-Ethynylated Naphthodiquinoline and Naphthodiacridine: Novel Diazabisacenes.

    Ahrens, Lukas / Maier, Steffen / Misselwitz, Erik / Oeser, Thomas / Rominger, Frank / Freudenberg, Jan / Bunz, Uwe H F

    Chemistry (Weinheim an der Bergstrasse, Germany)

    2021  Volume 27, Issue 41, Page(s) 10569–10573

    Abstract: The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki-coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel-Crafts acylation. The resulting diketones were alkynylated and reduced to give the ... ...

    Abstract The synthesis of two diazabisacenes is reported. A bisboronated naphthalene was Suzuki-coupled to substituted ethyl nicotinates, then cyclized by intramolecular Friedel-Crafts acylation. The resulting diketones were alkynylated and reduced to give the title compounds, bis(TIPS-ethynyl)-substituted naphtha[1,8-gh:5,4-g'h']diquinoline and naphtho[1,8-bc:5,4-b'c']diacridine. Nitrogen incorporation stabilizes the bisacenes with respect to oxidation compared to their consanguine nonaza analogs.
    MeSH term(s) Acylation ; Ketones ; Molecular Structure ; Oxidation-Reduction
    Chemical Substances Ketones
    Language English
    Publishing date 2021-05-27
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1478547-X
    ISSN 1521-3765 ; 0947-6539
    ISSN (online) 1521-3765
    ISSN 0947-6539
    DOI 10.1002/chem.202101246
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  10. Article ; Online: Sulfilimines as Versatile Nitrene Transfer Reagents: Facile Access to Diverse Aza-Heterocycles.

    Tian, Xianhai / Song, Lina / Rudolph, Matthias / Rominger, Frank / Oeser, Thomas / Hashmi, A Stephen K

    Angewandte Chemie (International ed. in English)

    2019  Volume 58, Issue 11, Page(s) 3589–3593

    Abstract: We herein report the unprecedented synthesis of diverse biologically important aza-heterocycles by employing sulfilimines as nitrene transfer reagents. This class of sulfur-based aza-ylides had not been successfully used for gold nitrene transfer before. ...

    Abstract We herein report the unprecedented synthesis of diverse biologically important aza-heterocycles by employing sulfilimines as nitrene transfer reagents. This class of sulfur-based aza-ylides had not been successfully used for gold nitrene transfer before. This work contains an efficient generation of α-imino gold carbenes by N-S cleavage of sulfilimines. These gold carbenes undergo C-H insertion, cyclopropanation, and nucleophilic attack to form indoles (44 examples), 3-azabicyclo[3.1.0]hexan-2-imines (24 examples), and imidazoles (3 examples). Our study represents a unique gold-catalyzed reaction between alkynes and sulfur ylides, and also includes the first aza-heterocycle synthesis that proceeds by intermolecular nitrene transfer followed by cyclopropanation of the α-imino gold carbenes. Moreover, an unexpected synthesis of 4-acylquinolines (3 examples) from 2-acylphenyl sulfilimines and propargylic silyl ether derivatives by a 1,2-hydride shift onto the α-imino gold carbene and a subsequent Mukaiyama aldol cyclization was discovered.
    Language English
    Publishing date 2019-01-31
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.201812002
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