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  • 1
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    Lipoproteins and Apolipoprotein Patterns in Rat Plasma after Liver Injury Induced by D-Galactosamine (1980)
    De Gruyter
    Details
    Publication Date: 1980-01-01
    Print ISSN: 0018-4888
    Topics: Biology , Chemistry and Pharmacology
    Published by De Gruyter
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  • 2
    Electronic Resource
    Electronic Resource
    Darstellung in 2-Stellung substituierter Indolderivate aus 3-Oxo-indolin-carbonsäure-(2)-estern (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 1869-1870 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Preparation of 2-Substituted Indole Derivatives from 3-Oxo-indolin-2-carboxylatesThe 3-Oxo-indolin-2-carboxylates 1a-1d with various substituents in the 2-position can be transformed in good yields into 2-substituted indoles 3a-3d by reduction followed by saponification, decarboxylation and dehydration.
    Notes: Die 2-alkylsubstituierten 3-Oxo-indolin-carbonsäure-(2)-ester 1a-1d lassen sich durch Reduktion, Verseifung, Decarboxylierung und Wasserabspaltung in guter Ausbeute in 2-alkylsubstituierte Indolderivate 3a-3d unwandeln.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040625
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  • 3
    Electronic Resource
    Electronic Resource
    Über die Alkylierung von Indoxyl-carbonsäure-(2)-estern und über die Claisen-Umlagerung der Allyloxyindole (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 1863-1868 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Alkylation of Indoxyl-2-carboxylates and Claisen Rearrangement of Allyloxyindoles2-(Ethoxycarbonyl)indoxyl (1) reacts with 1,1-dimethylallylchloride (3) to give 3-oxo-2-(3,3-dimethylallyl)-2-(ethoxycarbonyl)indoline (4) and 3-oxo-2-(1,1-dimethylallyl)-2-(ethoxycarbonyl)indoline (6). The corresponding reaction with 5,7-dibromo-2-(methoxycarbonyl)indoxyl (2) yields 5.7-dibromo-3-(3,3-dimethylallyloxy)-2-(methoxycarbonyl)indole (8) in addition to the C-alkylated products. A. Claisen-type rearrangement of this allylether 8 leads to formation of the C-alkylated compound 7.  -  Alkyltosylates react with 1 to yield the O-alkylated products 9-11. The reaction of allyltosylate with 1 gives mainly 3-(allyloxy)-2-(ethoxycarbonyl)indole (12), which rearranges on heating to the C-allyl derivative 13.
    Notes: Die Umsetzung von Indoxyl-carbonsäure-(2)-äthylester (1) mit 1.1-Dimethyl-allylchlorid (3) führt zu 3-Oxo-2-[3.3-dimethyl-allyl]-2-äthoxycarbonyl-indolin (4) und 3-Oxo-2-[1.1-dimethyl-allyl]-2-äthoxycarbonyl-indolin (6). Bei der entsprechenden Umsetzung mit 5.7-Dibromindoxyl-carbonsäure-(2)-ester erfolgt neben C-Alkylierung auch O-Alkylierung zu 5.7-Dibrom-3-[3.3-dimethyl-allyloxy]-2-methoxycarbonyl-indol (8), das sich thermisch in das C-Alkylderivat 7 umlagern läßt. Alkyltosylate reagieren mit 1 zu den O-alkylierten Produkten 9-11. Allyltosylat ergibt mit 1 in der Hauptsache 3-Allyloxy-indol-carbonsäure-(2)-ester 12, der sich beim Erhitzen in die C-Allylverbindung 13 umlagert.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19711040624
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  • 4
    Electronic Resource
    Electronic Resource
    Notiz zur Einführung von Dimethylallyl-Seitenketten in Indolderivate (1971)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 104 (1971), S. 2027-2029 
    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.19711040647
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  • 5
    Electronic Resource
    Electronic Resource
    Über Thio-Claisen-Umlagerungen in der Indolreihe (1974)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 107 (1974), S. 3915-3921 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Thio-Claisen Rearrangements in the Indole Series3-(Allylthio)indole (2) rearranges on heating to yield 2-allyl-3-indolethiol (6). Under the same conditions 3-(3,3-dimethylallylthio)indole (3) gives a mixture of 4,4-dimethyl-2,3,4,5-tetrahydrothiopyrano [3,2-b]indole (9) and 2-(1,1-dimethylallyl)indole (8). The reaction of 3 with methyl fluorosulfonate yields mainly 2 -(1,1-dimethylallyl)-3-(methylthio)indole (10), whereas the reaction of 3-(methylthio)indole (11) with 3,3-dimethylallyl bromide in methanol produces 1-(1,1-dimethylallyl)-3-(methylthio)indole (12). When the latter reaction is carried out in acetone, there occurs in addition to N-alkylation an attack at the sulfur atom and rearrangement to 13. - For the cleavage of the H3C-S bond in 3-(methylthio)indole the calcium-hexammine complex is very suitable. The 3-mercaptoindole which is formed during this reaction can be reduced to indole with Zn in acetic acid.
    Notes: 3-(Allylthio)indol (2) lagert sich beim Erhitzen in 2-Allyl-3-indolthiol (6) um. 3-(3,3-Dimethylallylthio)indol (3) gibt unter ähnlichen Reaktionsbedingungen ein Gemisch aus 4,4-Dimethyl- 2,3,4,5-tetrahydrothiopyrano[3,2-b]indol (9) und 2-(1,1-Dimethylallyl)indol (8). Bei der Umsetzung von 3 mit Fluorsulfonsäure-methylester entsteht hauptsächlich 2-(1,1-Dimethylallyl)-3-(methylthio)indol (10). Läßt man dagegen 3-(Methylthio)indol (11) mit 3,3-Dimethylaiiylbromid in Methanol reagieren, so bildet sich 1-(1,1-Dimethylallyl)-3-(methylthio)indol (12). Bei der gleichen Reaktion in Aceton findet außer einer Alkylierung am Stickstoff ein Angriff am Schwefel und eine Umlagerung zu 13 statt. - Zur Spaltung der H3C-S-Bindung eignet sich beim 3-(Methylthio)indol der Calcium-hexammin-Komplex in Äther. Das entstandene 3-Mercaptoindol kann mit Zink/Eisessig zum Indol reduziert werden.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19741071223
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