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  • 1975-1979  (4)
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  • 1
    Electronic Resource
    Electronic Resource
    Chemie der Amino-oxime, XI: Über die Synthese von 2-Oxo-3-imidazolin-3-oxiden und ihre Prototropie (1978)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 111 (1978), S. 1171-1179 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Chemistry of Amino Oximes, XI: The Synthesis of 2-Oxo-3-imidazoline 3-Oxides and Their PrototropyAnti(E)-α-amino oximes (1) with different substituents were cyclized with phosgene as well as by hydrolysis of the corresponding urethanes 7 to give 2-oxo-3-imidazoline 3-oxides. The structure were proved by cycloaddition and by spectroscopic methods. Tautomerisms were observed in the case of oximes with α-H-atoms. In one example, 3-hydroxy-4-imidazolin-2-one (9i) was formed. in an other one the N-hydroxy-exo-methylene compound 10c, which undergoes cycloaddition with the parent N-oxide (3c) to yield an isoxazolidine 11c.
    Notes: Verschieden substituierte anti(E)-α-Amino-oxime (1) wurden mit Phosgen oder durch Verseifen der entsprechenden Urethane 7 zu 2-Oxo-4-imidazolin-3-oxiden (3) cyclisiert. Die Konstitution wurde durch Cycloaddition und spektroskopisch bestätigt. Bei Oximen mit α-ständigen H-Atomen trat in einem Fall Tautomerie zum 3-Hydroxy-4-imidzolin-2-on (9i) ein, im anderen zur N-Hydroxy-exo-methylen-Verbindung 10c. Letztere bildet mit dem N-Oxid 3c durch Cycloaddition ein Isoxazolidin-Derivat 11c.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19781110335
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  • 2
    Electronic Resource
    Electronic Resource
    Chemie der Amino-oxime, X. Die Umsetzung von syn-ω-Aminopropiophenon-oximen mit Phosgen und 1,1′-Carbonyldiimidazol (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 3387-3396 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Chemistry of Amino Oximes, X. The Reactions of,synω- Aminopropiophenone Oximes with Phosgene and 1,1′carbonyldimidazole;- primesyn-ω-(Benzylamino)propiophenone oximes react with phosgene to give 3-(benzylamino)propionanilides (3). 1,7-dioxoperhydrodiphyrimido [3,4-b:3′,4′-e][1,4,2,5]dioxadiazines (5), and 7-oxo-4,5,6,7-tetrahydro-1,2,6-oxadiazepines (4) as main products. The reaction with 1,1′-carbonyldiimidazole leads preferably to 5. The Structures were proved by spectroscopic and chemical methods.
    Notes: Aus syn-ω-(Benzylamino)propiophenon-oximen werden mit Phosgen neben 3-(Benzylamino)-propionaniliden (3) und 1,7-Dioxoperhydrodipyimido[3,4-b:3′,4′-e][1,4,2,5]dioxadiazinen (5) als Hauptprodukt 7-Oxo-4,5,6,7-oxadiazepine (4) erhalten. Die Reaktion führt mit 1,1′-Carbonyldimidazol überwiegend zu 5. Die Strukturen wurden auf spektroskopischen und chemischen Wegen bestimmt.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751081030
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  • 3
    Electronic Resource
    Electronic Resource
    Chemie der Amino-oxime, IX. Synthese und Konfigurationsbestimmung von ω-Aminopropio-phenon-oximen (1975)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 108 (1975), S. 3380-3386 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Chemistry of Amino Oximes, IX. The Synthesis and the Configuration of ω-Aminopropiophenone OximesThe synthesis of ω-aminopropiophenone oximes (6) by hydrazinolysis of ω-phthalimidopropiophenone oximes (5) is described. Both the ω-amino- and the ω-phthalimidopropiophenone oximes show syn(Z) configuration, proved by Beckmann rearrangement and u. v. spectra. The reaction with phosgene leads to the anilides 8, formed from 6 by Beckmann rearrangement, and the bisamides derived from 6 and 8.
    Notes: Die Synthese von ω-Aminopropiophenon-oximen (6) durch Hydrazinolyse der ω-Phthalimido-propiophenon-oxime (5) wird beschrieben. Sowohl die ω-Amino-als auch die ω-Phthalimidopropio-phenon-oxime haben syn(Z)-Konfiguration, wie die Beckmann-Umlagerung und die UV-Spektren zeigen. Mit Phosgen entstehen aus 6 durch Beckmann-Umlagerung die Anilide 8, sowie die sich aus 6 und 8 ableitenden Bisamide.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19751081029
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  • 4
    Electronic Resource
    Electronic Resource
    Isomere Heterocyclen durch Cyclisierung von syn- und anti-α-Aminohydrazonen (1978)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1978 (1978), S. 2033-2043 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Isomeric Heterocycles by Cyclisation of syn- and anti-α-Amino HydrazonesThe syn- and anti-α-amino hydrazones 1 and 2, respectively, were prepared. The syn-isomers 1 react with formaldehyde and with phosgene to give the 1,2,4-triazines 3 and 4, respectively. The anti-isomers 2 cyclise with phosgene giving the 1-anilinoimidazolin-2-ones 5, or if C-α is a tertiary atom the 1-anilino-5-methyleneimidazolidin-2-ones 8.  -  On mass spectroscopy, compounds 5 and 8 show the characteristic exocyclic amine fragment. Structures were established by spectroscopic methods supplemented by complexation studies on the α-amino hydrazones.
    Notes: Es wurden die syn- sowie anti-α-Aminohydrazone 1 bzw. 2 hergestellt und ihre Konfigurationen spektroskopisch und durch Komplexbildung bestimmt. Aus 1 entstehen durch Umsetzung mit Formaldehyd oder Phosgen die 1,2,4-Triazin-Derivate 3 bzw. 4. Die anti-Verbindungen 2 cyclisieren mit Phosgen zu 1-Anilino-4-imidazolin-2-onen 5, wenn C-α ein tertiäres C-Atom ist aber zu 1-Anilino-5-methylenimidazolidin-2-onen 8.  -  Die Struktur der Heterocyclen wurde spektroskopisch bestätigt. 5 und 8 sind massenspektrometrisch durch Abspaltung des exocyclischen Aminfragmentes charakterisiert.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197819781219
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