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  1. Article: Straightforward Synthesis of Highly Functionalized Indanes and Tetralines through Ene-Cyclopropene Rearrangement Mediated by Ruthenium

    Puet, Alejandro / Domínguez, Gema / Pérez-Castells, Javier

    Journal of organic chemistry. 2022 Feb. 04, v. 87, no. 5

    2022  

    Abstract: Ene-cyclopropenes give functionalized indanes and tetralines in the presence of ruthenium dimeric catalysts. This reaction involves the cyclopropene opening by the metal catalysts with a different regioselectivity respective to gold chlorides and ... ...

    Abstract Ene-cyclopropenes give functionalized indanes and tetralines in the presence of ruthenium dimeric catalysts. This reaction involves the cyclopropene opening by the metal catalysts with a different regioselectivity respective to gold chlorides and produces totally different products than when using semisandwich ruthenium complexes. Here, the process leads to a bridged 7-oxanorbornene-type intermediate that is converted into a functionalized aromatic ring through deoxygenative aromatization. Alternative reaction pathways occur with substrates with no possible aromatization.
    Keywords aromatic compounds ; aromatization ; gold ; organic chemistry ; regioselectivity ; ruthenium
    Language English
    Dates of publication 2022-0204
    Size p. 2686-2696.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.1c02636
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

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  2. Article ; Online: Straightforward Synthesis of Highly Functionalized Indanes and Tetralines through Ene-Cyclopropene Rearrangement Mediated by Ruthenium.

    Puet, Alejandro / Domínguez, Gema / Pérez-Castells, Javier

    The Journal of organic chemistry

    2022  Volume 87, Issue 5, Page(s) 2686–2696

    Abstract: Ene-cyclopropenes give functionalized indanes and tetralines in the presence of ruthenium dimeric catalysts. This reaction involves the cyclopropene opening by the metal catalysts with a different regioselectivity respective to gold chlorides and ... ...

    Abstract Ene-cyclopropenes give functionalized indanes and tetralines in the presence of ruthenium dimeric catalysts. This reaction involves the cyclopropene opening by the metal catalysts with a different regioselectivity respective to gold chlorides and produces totally different products than when using semisandwich ruthenium complexes. Here, the process leads to a bridged 7-oxanorbornene-type intermediate that is converted into a functionalized aromatic ring through deoxygenative aromatization. Alternative reaction pathways occur with substrates with no possible aromatization.
    Language English
    Publishing date 2022-02-04
    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.1c02636
    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:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

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  3. Article: Cobalt catalysed aminocarbonylation of thiols in batch and flow for the preparation of amides

    Orduña, Jose Maria / Domínguez, Gema / Pérez-Castells, Javier

    RSC advances. 2021 Sept. 13, v. 11, no. 48

    2021  

    Abstract: The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the ... ...

    Abstract The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the formation of disulfides and ureas can be limited. The process works well with aromatic thiols with electron donating groups (EDG) whereas other thiols give reaction with lower yields. The previous process has been transferred and optimized into flow equipment, thus allowing using less CO in a safer way, and permitting the scaling up of the synthesis. Two drugs, moclobemide and itopride were prepared with this methodology, albeit only in the second case with good results. A mechanistic pathway is proposed.
    Keywords amides ; cobalt ; disulfides ; equipment ; thiols
    Language English
    Dates of publication 2021-0913
    Size p. 30398-30406.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ISSN 2046-2069
    DOI 10.1039/d1ra04736a
    Database NAL-Catalogue (AGRICOLA)

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  4. Article ; Online: Study of the Pauson-Khand reaction in flow over alkynylphenyl vinyl ethers: towards the synthesis of tricyclic multisubstituted benzofurans.

    García-Lacuna, Jorge / Alonso, Maialen / Domínguez, Gema / Pérez Castells, Javier

    RSC advances

    2022  Volume 12, Issue 12, Page(s) 7313–7317

    Abstract: The use of flow methodology allows the use of alkynylphenyl vinyl ethers (benzo-fused 1,7 enynes) as substrates for the intramolecular Pauson-Khand reaction (PKr). Forced temperature and pressure conditions during a short reaction time minimize the ... ...

    Abstract The use of flow methodology allows the use of alkynylphenyl vinyl ethers (benzo-fused 1,7 enynes) as substrates for the intramolecular Pauson-Khand reaction (PKr). Forced temperature and pressure conditions during a short reaction time minimize the substrate decomposition allowing the formation of the PK adduct. Substrates substituted at the internal position of the double bond and with internal triple bonds give better yields. The resulting products are cyclopentabenzofuranones present in diverse natural products and drugs that can be further functionalised.
    Language English
    Publishing date 2022-03-04
    Publishing country England
    Document type Journal Article
    ISSN 2046-2069
    ISSN (online) 2046-2069
    DOI 10.1039/d2ra01062c
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  5. Article ; Online: Cobalt catalysed aminocarbonylation of thiols in batch and flow for the preparation of amides.

    Orduña, Jose Maria / Domínguez, Gema / Pérez-Castells, Javier

    RSC advances

    2021  Volume 11, Issue 48, Page(s) 30398–30406

    Abstract: The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the ... ...

    Abstract The synthesis of amides from thiols through a cobalt-catalyzed aminocarbonylation is shown. After optimizing all the reaction parameters, the methodology makes possible the obtention of amides with variable yields, while competing reactions such as the formation of disulfides and ureas can be limited. The process works well with aromatic thiols with electron donating groups (EDG) whereas other thiols give reaction with lower yields. The previous process has been transferred and optimized into flow equipment, thus allowing using less CO in a safer way, and permitting the scaling up of the synthesis. Two drugs, moclobemide and itopride were prepared with this methodology, albeit only in the second case with good results. A mechanistic pathway is proposed.
    Language English
    Publishing date 2021-09-13
    Publishing country England
    Document type Journal Article
    ISSN 2046-2069
    ISSN (online) 2046-2069
    DOI 10.1039/d1ra04736a
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    Kategorien

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  6. Article ; Online: One Pot Synthesis of Spirocycles and Cyclopropa[

    Puet, Alejandro / Giona, Eleonora / Domínguez, Gema / Pérez-Castells, Javier

    The Journal of organic chemistry

    2022  Volume 87, Issue 18, Page(s) 12470–12476

    Abstract: A one pot alkenylation followed by a stereoselective Alder-ene cycloisomerization of cyclopropenes give (aza)spiro[2.4]heptanes and spiro[2.5]octanes in high yields. ... ...

    Abstract A one pot alkenylation followed by a stereoselective Alder-ene cycloisomerization of cyclopropenes give (aza)spiro[2.4]heptanes and spiro[2.5]octanes in high yields. Total
    Language English
    Publishing date 2022-08-30
    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.2c01420
    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:
    Je nach Verfügbarkeit (siehe Angabe bei Bestand)
    bis Jg. 1994: Bestellungen von Artikeln über das Online-Bestellformular
    Jg. 1995 - 2021: Lesesall (2.OG)
    ab Jg. 2022: Lesesaal (EG)

    Order via subito

    This service is chargeable due to the Delivery terms set by subito. Orders including an article and supplementary material will be classified as separate orders. In these cases, fees will be demanded for each order.

  7. Article: Study of the Pauson–Khand reaction in flow over alkynylphenyl vinyl ethers: towards the synthesis of tricyclic multisubstituted benzofurans

    García-Lacuna, Jorge / Alonso, Maialen / Domínguez, Gema / Pérez Castells, Javier

    RSC advances. 2022 Mar. 04, v. 12, no. 12

    2022  

    Abstract: The use of flow methodology allows the use of alkynylphenyl vinyl ethers (benzo-fused 1,7 enynes) as substrates for the intramolecular Pauson–Khand reaction (PKr). Forced temperature and pressure conditions during a short reaction time minimize the ... ...

    Abstract The use of flow methodology allows the use of alkynylphenyl vinyl ethers (benzo-fused 1,7 enynes) as substrates for the intramolecular Pauson–Khand reaction (PKr). Forced temperature and pressure conditions during a short reaction time minimize the substrate decomposition allowing the formation of the PK adduct. Substrates substituted at the internal position of the double bond and with internal triple bonds give better yields. The resulting products are cyclopentabenzofuranones present in diverse natural products and drugs that can be further functionalised.
    Keywords benzofurans ; drugs ; ethers ; temperature
    Language English
    Dates of publication 2022-0304
    Size p. 7313-7317.
    Publishing place The Royal Society of Chemistry
    Document type Article
    ISSN 2046-2069
    DOI 10.1039/d2ra01062c
    Database NAL-Catalogue (AGRICOLA)

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  8. Article: One Pot Synthesis of Spirocycles and Cyclopropa[b]pyrans by Alkenylation-Rearrangement of Cyclopropenes

    Puet, Alejandro / Giona, Eleonora / Domínguez, Gema / Pérez-Castells, Javier

    Journal of organic chemistry. 2022 Aug. 30, v. 87, no. 18

    2022  

    Abstract: A one pot alkenylation followed by a stereoselective Alder-ene cycloisomerization of cyclopropenes give (aza)spiro[2.4]heptanes and spiro[2.5]octanes in high yields. Total trans diastereoselectivity is achieved for spiro[2.4]heptanes if the cyclopropene ... ...

    Abstract A one pot alkenylation followed by a stereoselective Alder-ene cycloisomerization of cyclopropenes give (aza)spiro[2.4]heptanes and spiro[2.5]octanes in high yields. Total trans diastereoselectivity is achieved for spiro[2.4]heptanes if the cyclopropene is monosubstituted in C3. When an α,β-unsaturatedcarbonyl-containing bromide is used, an alternative cyclization takes place giving cyclopenta[c]cyclopropa[b]pyrans.
    Keywords diastereoselectivity ; organic chemistry ; pyrans
    Language English
    Dates of publication 2022-0830
    Size p. 12470-12476.
    Publishing place American Chemical Society
    Document type Article
    ZDB-ID 123490-0
    ISSN 1520-6904 ; 0022-3263
    ISSN (online) 1520-6904
    ISSN 0022-3263
    DOI 10.1021/acs.joc.2c01420
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Bonn / Germany

    Z 4' 49/42: Show issues
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  9. Article ; Online: Flow Chemistry for Cycloaddition Reactions.

    García-Lacuna, Jorge / Domínguez, Gema / Pérez-Castells, Javier

    ChemSusChem

    2020  Volume 13, Issue 19, Page(s) 5138–5163

    Abstract: Continuous flow reactors form part of a rapidly growing research area that has changed the way synthetic chemistry is performed not only in academia but also at the industrial level. This Review highlights the most recent advances in cycloaddition ... ...

    Abstract Continuous flow reactors form part of a rapidly growing research area that has changed the way synthetic chemistry is performed not only in academia but also at the industrial level. This Review highlights the most recent advances in cycloaddition reactions performed in flow systems. Cycloadditions are atom-efficient transformations for the synthesis of carbo- and heterocycles, involved in the construction of challenging skeletons of complex molecules. The main advantages of translating these processes into flow include using intensified conditions, safer handling of hazardous reagents and gases, easy tuning of reaction conditions, and straightforward scaling up. These benefits are especially important in cycloadditions such as the copper(I)-catalyzed azide alkyne cycloaddition (CuAAC), Diels-Alder reaction, ozonolysis and [2+2] photocycloadditions. Some of these transformations are key reactions in the industrial synthesis of pharmaceuticals.
    Language English
    Publishing date 2020-08-18
    Publishing country Germany
    Document type Journal Article ; Review
    ISSN 1864-564X
    ISSN (online) 1864-564X
    DOI 10.1002/cssc.202001372
    Database MEDical Literature Analysis and Retrieval System OnLINE

    Full text online

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  10. Article ; Online: Synthesis and Evaluation of Novel Iminosugars Prepared from Natural Amino Acids.

    Puet, Alejandro / Domínguez, Gema / Cañada, Francisco Javier / Pérez-Castells, Javier

    Molecules (Basel, Switzerland)

    2021  Volume 26, Issue 2

    Abstract: Cyclopropanated iminosugars have a locked conformation that may enhance the inhibitory activity and selectivity against different glycosidases. We show the synthesis of new cyclopropane-containing piperidines bearing five stereogenic centers from natural ...

    Abstract Cyclopropanated iminosugars have a locked conformation that may enhance the inhibitory activity and selectivity against different glycosidases. We show the synthesis of new cyclopropane-containing piperidines bearing five stereogenic centers from natural amino acids l-serine and l-alanine. Those prepared from the latter amino acid may mimic l-fucose, a natural-occurring monosaccharide involved in many molecular recognition events. Final compounds prepared from l-serine bear
    MeSH term(s) Amino Acids/chemistry ; Animals ; Biological Products/chemistry ; Coffee/enzymology ; Enzyme Inhibitors/chemical synthesis ; Enzyme Inhibitors/chemistry ; Enzyme Inhibitors/pharmacology ; Geobacillus stearothermophilus/enzymology ; Glycoside Hydrolases/antagonists & inhibitors ; Glycoside Hydrolases/metabolism ; Helix, Snails/enzymology ; Imino Sugars/chemical synthesis ; Imino Sugars/chemistry ; Imino Sugars/pharmacology ; Molecular Structure ; Phaseolus/enzymology
    Chemical Substances Amino Acids ; Biological Products ; Coffee ; Enzyme Inhibitors ; Imino Sugars ; Glycoside Hydrolases (EC 3.2.1.-)
    Language English
    Publishing date 2021-01-13
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1413402-0
    ISSN 1420-3049 ; 1431-5165 ; 1420-3049
    ISSN (online) 1420-3049
    ISSN 1431-5165 ; 1420-3049
    DOI 10.3390/molecules26020394
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    Zs.MO 81: Show issues

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