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  • 1
    Electronic Resource
    Electronic Resource
    Synthesis of (1R,3R,5S)-1-Amino-3-(hydroxymethyl)bicyclo[3.1.0]hexane as a Precursor for the Synthesis of Carbocyclic Nucleosides (1994)
    s.l. : American Chemical Society
    The @journal of organic chemistry 59 (1994), S. 5336-5342 
    Details
    ISSN: 1520-6904
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/jo00097a040
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Acetylenchemie 7. Mitt.: Mechanistische Studien zur Synthese von Pyrano-[3,2-c]chinolin-Alkaloiden aus 4-Hydroxychinolin-2-onen und 3-Chlor-3-methylbut-1-in (1988)
    Springer
    Monatshefte für Chemie 119 (1988), S. 781-791 
    Details
    ISSN: 1434-4475
    Keywords: Pyrano[3,2-c]quinoline-alkaloids ; 4-Hydroxyquinoline-2-ones ; Alkylation ; Phase-transfer-catalysis ; Sigmatropic rearrangement ; “Späth type” chromene synthesis
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Notes: Abstract The pyrano-cyclisation of 4-hydroxy-(1-methyl)-1H-quinoline-2-one with 3-chlor-3-methylbut-1-yne, supposed to proceed via an ether or vinyl intermediate, is studied by alkylating different 4-hydroxyquinolines. The nine derivatives characterized favour the ether-pathway (“Späth type” chromene synthesis).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF00809691
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  • 3
    Electronic Resource
    Electronic Resource
    Naturstoffchemie, 114. Dictamnin und Derivate durch Pd/Cu-katalysierte Alkin-Kupplung (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 69-73 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Natural Product Chemistry, 114. - Dictamnine and Derivatives by Pd/Cu-Catalysed Alkyne CouplingThe Pd/Cu-catalysed reaction of 3-iodo-4-methoxy-2(1H)-quinolinone (6) with (trimethylsilyl)ethyne yields 2-(trimethylsilyl)dictamnine (4) or the coupling product 3. The furoquinoline alkaloid dictamnine (1) is obtained by addition of fluoride to 4. The deuteriodesilylation of 4 to [2-D1]dictamnine (1a) is also possible. Further 1-alkynes afford 2-substituted furo[2,3-b]quinolines. With 2-methyl-3-butyn-2-ol the coupled quinoline 9 is available, too. Starting with ethyl propiolate, the N-vinyl adduct 12 is generated.
    Notes: Durch die Pd/Cu-katalysierte Reaktion von 3-Iod-4-methoxy-2(1H)-chinolinon (6) mit (Trimethylsilyl)acetylen entsteht 2-(Trimethylsilyl)dictamnin (4) bzw. das Kupplungsprodukt 3. Das Furochinolin-Alkaloid Dictamnin (1) bildet sich aus 4 bei Fluorid-Zusatz. Die Deuteriodesilylierung von 4 zu [2-D1]Dictamnin (1a) ist ebenfalls möglich. Weitere 1-Alkine ergeben 2-substituierte Furo[2,3-b]chinoline. Mit 2-Methyl-3-butin-2-ol ist auch das gekuppelte Chinolin 9 zugänglich, mit Propiolsäure-ethylester fällt das N-Vinyladdukt 12 an.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880113
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  • 4
    Electronic Resource
    Electronic Resource
    Naturstoffchemie, 1181) Synthese der Cumarine 6- und 8-Naphthoherniarin, Dehydrogeijerin und Murraol (1988)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1988 (1988), S. 543-547 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Natural Product Chemistry, 1181). - Synthesis of the Coumarins 6- and 8-Naphthoherniarin, Dehydrogeijerin, and MurraolThe Pd/Cu-catalysed reaction of 6-bromo-7-methoxycoumarin (1) with 2-Methyl-3-butyn-2-ol yields 1,2-dehydrosuberenol (2). By Lindlar reduction, water elimination, Diels-Alder reaction with 2-methoxy-p-benzoquinone (6), and dehydrogenation with 6-naphthoherniarin (9), a novel coumarin from Ruta graveolens is synthesized. Dehydrogeijerin (8) is available by Schuster-Meyer rearrangement of 2. By Heck vinylation 8-iodo-7-methoxycoumarin (11) is transferred into murraol (12). By water elimination from 12, Diels-Alder reaction with 6 and aromatisation 8-naphthoherniarin (14) is available.
    Notes: Aus 6-Brom-7-methoxycumarin (1) und 2-Methyl-3-butin-2-ol wird unter Pd/Cu-Katalyse 1,2-Dehydrosuberenol (2) gewonnen. Die Lindlar-Hydrierung, Wasserabspaltung, Diels-Alder-Reaktion mit 2-Methoxy-p-benzochinon (6) und Dehydrierung führen zu 6-Naphthoherniarin (9), einem neuartigen Cumarin aus Ruta graveolens. Dehydrogeijerin (8) ist durch Schuster-Meyer-Umlagerung von 2 erhältlich. 8-Iod-7-methoxycumarin (11) wird mittels Heck-Vinylierung zu Murraol (12) umgesetzt. Nach Wasserabspaltung aus 12, Diels-Alder-Reaktion mit 6 und Aromatisierung bildet sich 8-Naphthoherniarin (14).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198819880609
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