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  • 1
    Electronic Resource
    Electronic Resource
    Brucin aus Strychnin (1968)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 101 (1968), S. 2754-2757 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Aus 2-Hydroxy-strychin (1) wird mittels der Fremy-Salz-Oxydation über Brucichinon 2.3-Dihydroxy-strychnin (2) erhalten. Dessen N-Oxid (3) wird mittels Dimethylsulfat in Brucin-N-oxid (4) übergeführt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19681010819
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  • 2
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie des Indols, II Beckmann-und Schmidt-Umlagerungen an einigen Indolketonen (1970)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 103 (1970), S. 496-509 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Contributions to the Chemistry of Indole, II Beckmann and Schmidt Rearrangements of some Indole KetonesSchmidt rearrangement of serveral indole ketones resulted in the migration of the C atom bearing the indole group to yield one amide, whereas Beckmann rearrangement led to the formation of the isomeric amide. A H-bridge between indole-NH and oxime group might be responsible for the unusual behavior of these compounds in the Beckmann rearrangement.
    Notes: Die hier untersuchten Indolyl-(2)-2′ -ketone ergeben bei der Schmidt-Reaktion selektiv ein Amid unter Wanderung des C-Atoms, das den Indolrest trägt, bei der Beckmann-Umlagerung dagegen selektiv das andere Isomere. Für das anormale Verhalten bei der Beckmann-Umlagerung kann möglicherweise eine H-Brücke, die zu spezifischer Fixierung der Oxime führt, eine Erklärung geben.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19701030219
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  • 3
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie des Indols, IX1) Synthesen in der β-Carbolinreihe, I. Eine neue Darstellung von Canthin-6-on sowie Synthese einiger Indolo[2,3-a]chinolizine (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 705-709 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Contributions to the Chemistry of Indole, IX1) Syntheses in th β-Carboline Series, I. A New Synthesis of Canthin-6-one and Syntheses of Some Indolo[2,3-a]quinolizinesFrom methyl cumalate and tryptamine the compounds 6, 7, and 8a are synthesized via 4a. 2 reacts with nitrous acid to give canthin-6-one (3) in a 15 per cent yield.
    Notes: Aus Cumalinsäure-methylester und Tryptamin werden über 4a die Verbindungen 6, 7 und 8a erhalten. 2 ergibt mit salpetriger Säure zu 15% Canthin-6-on (3).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761090232
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  • 4
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie des Indols, XI. Synthesen und Eigenschaften vor 2-(2-Indolyl)-1,3-dicarbonyl-verbindungen, I (Entaromatisierungseffekte in der Indolreihe) (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 3282-3291 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Contributions to the Chemistry of Indole, XISyntheses and Properties of 2-(2-Indolyl)-1,3-dicarbonyl Compounds, 1 (Dearomatisation Effects in the Indole Series)2-Nitrophenylacetyl chloride reacts with the Na salts of CH-acidie compounds to give the 2-nitrobenzyl ketones 7 which are catalytically reduced to the 2-indolyl derivatives 10.
    Notes: 2-Nitrophenylacetylchlorid reagiert mit den Na-Salzen CH-acider Verbindungen zu den 2-Nitrobenzylketonen 7, die zu den 2-Indolylderivaten 10 katalytisch reduziert werden.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761091003
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  • 5
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie des Indols, III. Desäthyl-chano-ibogamin (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 1379-1386 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Contributions to the Chemistry of Indole, III. Deethyl-chano-ibogamine2-(2-Indolyl)cyclohexanone (3) was hydrogenated in the presence of methylamine to give the cis-methylamine 4a, which was treated with ethyl bromoacetate. The resulting ethyl aminoacetate 8a was saponified and cyclisized with PPA yielding the ketone 9, which on reduction with LiAlH4 almost quantitatively afforded the title compound 2 possessing cis-configuration between the rings C and D.
    Notes: Aus 2-[Indolyl-(2)]-cyclohexanon (3) erhält man durch hydrierende Aminierung das Methylamin 4 als cis/trans-Isomerengemisch. Das cis-Amin (4a) wird mit Bromessigester umgesetzt, der entstehende Aminosäureester 8a verseift und die Säure (8b) mittels PPA zum 8-Oxodesäthyl-chano-ibogamin (9) cyclisiert. Aus diesem erhält man mit LiAlH4 fast quantitativ die Titelverbindung 2.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040506
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  • 6
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie des Indols, IV. Synthesen in der Iboga-Reihe, I. (d,l)-Desäthylibogamin (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 1459-1473 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Contributions to the Chemistry of Indole, IV1) Syntheses in the Iboga-Series, I. (d,l)-DesethylibogamineThe enamine 6 of ethyl 4-Oxo-1-cyclohexanecarboxylate reacts with o-nitrophenylacetyl chloride to give the 1,3-diketone 7. This on reductive cyclization forms ethyl cis-3-(2-indolyl)-4-oxo-1-cyclohexanecarboxylate (9), which as the oxime is reduced primarily to the cis-amine 15. Lactam ring closure to the isochinuclidone 17, reduction to the isochinuclidine 18, and azepine ring closure using a new method yield the title compound 3 in nine steps.
    Notes: Das Enamin 6 des 4-Oxo-1-cyclohexancarbonsäure-äthylesters wird mit o-Nitrophenylacetylchlorid zum 1,3-Diketon 7 umgesetzt. Bei dessen reduktiver Cyclisierung entsteht in guter Ausbeute der cis-3-(2-Indolyl)-4-oxo-1-cyclohexancarbonsäure-äthylester (9), welcher als Oxim 9a überwiegend zum cis-Amin 15 reduziert wird. Lactamringschluß zu 17, Reduktion zum Isochinuclidin 18 und Azepinringschluß nach einer neuen Methode liefert in neun Stufen die Titelverbindung 3.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060511
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  • 7
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie des Indols, V. Synthesen in der Iboga-Reihe, II. 8-Oxodesäthylibogain und Desäthylisoibogain (1973)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 106 (1973), S. 1474-1482 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Contributions to the Chemistry of Indole, V. Syntheses in the Iboga-Series, II. 8-Oxodeethylibogaine and Deethylisoibogaine5-Methoxy-2-nitrophenylacetyl chloride reacts with the morpholine-enamine of ethyl 4-oxo-1-cyclohexanecarboxylate to give the diketone 7. Catalytic hydrogenation of 7 and treatment with hydroxylamine yields the oximes of the stereoisomers of the indole ketones 8 and 9. Katalytic hydrogenation of the oxime of 8 under pressure preferably yields the cis-amine 11, which cyclizes under N2 to form the isoquinuclidone 12. Under CO2, however, the N-acylindole 14 is formed in considerable amounts. Reduction of the isoquinuclidone 12 with LiAlH4 followed by treatment with ethyl bromoacetate and PPA-cyclization leads to the 8-oxodeethylibogaine 16 in poor yield. Isoquinuclidine 13 and acetaldehyde react via intramolecular Mannich condensation to give deethylisoibogaine (6).
    Notes: 5-Methoxy-2-nitrophenylacetylchlorid liefert mit dem Morpholin-Enamin von 4-Oxo-1-cyclohexancarbonsäure-äthylester das Diketon 7, welches nach katalytischer Hydrierung und Behandlung mit Hydroxylaimin das Stereoisomerengemisch der Oxime der Indolketone 8 und 9 ergibt. Aus dem 8-Oxim entsteht durch katalytische Druckhydrierung bevorzugt das cis-Amin 11, welches unter N2 das Isochinuclidon 12 liefert. Unter CO2 dagegen bildet sich in beträchtlicher Menge die N-Acylindolverbindung 14. Reduktion des Isochinuclidons mit LiAIH4, Umsetzung mit Bromessigester und Polyphosphorsäure-Cyclisierung lassen in mäßiger Ausbeute das 8-Oxodesäthylibogain 16 entstehen. Aus dem Isochinuclidin 13 und Acetaldehyd entsteht in innermolekularer Mannich-Reaktion das Desäthylisoibogain (6).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19731060512
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  • 8
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie des Indols, VIII. Decarboxylierungen einiger 1-Alkyl-2-carboxy-3-indolessigsäuren sowie Synthese eines 5-Thiocyanato-2,3-dihydroindols (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 3538-3542 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Not mentioned2a-d, easily produced from the N-alkyl-N-phenylhydrazines 1a-d and 2-oxoglutaric acid, are decarboxylated to the compounds 4a-d in high yields. 2a is reduced to the 2,3-dihydro compound 3a and reacts via the amide 5a to the 5-thiocyanato derivative 6a.
    Notes: Contributions to the Chemistry of Indole, VIII. Decarboxylations of Some 1-Alkyl-2-carboxy-3-indolacetic Acids and Synthesis of a 5-Thiocyanato-2,3-dihydroindole-d, leicht darstellbar aus N-Alkyl-N-phenylhydrazin und 2-Oxoglutarsäure, werden mit hoher Ausbeute zu 4a-d decarboxyliert. 2a wird zum Dihydroindol 3a reduziert und über das Amid 5a zum 5-Thiocyanatoderivat 6a umgesetzt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751081115
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  • 9
    Electronic Resource
    Electronic Resource
    Notiz zur Synthese des [2,6-Bis(methoxycarbonyl)-5,6-dihydro-4H-pyran-4-yliden]essigsäure-methylesters (1976)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 109 (1976), S. 3486-3488 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19761091028
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  • 10
    Electronic Resource
    Electronic Resource
    Beiträge zur Chemie des Indols, VII. Synthesen in der Iboga-Reihe, III. Ibogamin, Ibogain und Epiibogamin (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 1871-1895 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Contributions to the Chemistry of Indole, VII. Syntheses in the Iboga-Series, III. Ibogamine, Ibogaine, and EpiibogamineStarting from dimethyl malonate, methyl acrylate, o-nitrotoluene, diethyl oxalate, ethyl bromoacetate, and hydroxylamine, both the iboga and epiiboga alkaloids have been synthesised stereoselectively in only fourteen steps by a novel indole synthesis. This synthesis proves the configuration.
    Notes: Ausgehend von Malon- und Acrylester, o-Nitrotoluol, Oxalester, Bromessigester und Hydroxylamin werden in 14 Stufen jeweils stereoselektiv sowohl die Iboga- als auch die Epiiboga-Alkaloide nach einer neuen Indolsynthese erhalten. Diese Synthesen sind konfigurationsbeweisend.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751080611
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