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  • 1980-1984  (5)
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  • 1
    Electronic Resource
    Electronic Resource
    Synthese und Eigenschaften von 4-Benzyloxyimino- und 4-Hydroxyimino-1,3-dioxan-2-one (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 1177-1184 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Synthesis and Properties of 4-benzyloximino- and 4-Hydroxyimino-1,3-dioxan-2-onesUnder suitable conditions the reaction of N-benzyloxy-3-hydroxycarboxamides 7 with phosgene produces 3-benzyloxy-5,6-dihydro-2H-1,3-oxazine-2,4(3H)-diones 8 and 4-benzyloxyimino-1,3-dioxan-2-ones 6. Hydrogenolysis of 6 gives 4-hydroxyimino-1,3-dioxan-2-ones 4 which rearrange in the presence of imidazole into 5,6-dihydro-3-hydroxy-2H-1,3-oxazine-2,4(3H)-diones 5. Treatment of 4a, c with trifluoroacetic anhydride or 4-nitrobenzoyl chloride yields 4-acyloxyimino-1,3-dioxan-2-ones 9.
    Notes: N-Benzyloxy-3-hydroxycarbonsäureamide 7 reagieren mit Phosgen unter geeigneten Bedingungen zu 3-Benzyloxy-5,6-dihydro-2H-1,3-oxazin-2,4(3H)-dionen 8 und 4-Benzyloxyimino-1,3-dioxan-2-onen 6. Die katalytische Hydrierung von 6 ergibt 4-Hydroxyimino-1,3-dioxan-2-one 4, welche in Gegenwart von Imidazol zu 5,6-Dihydro-3-hydroxy-2H-1,3-oxazin-2,4(3H)-dionen 5 isomerisieren. Aus den Umsetzungen von 4a, c mit Trifluoracetanhydrid oder 4-Nitrobenzoylchlorid erhält mit in glatter Reaktion 4-Acyloxyimino-1,3-dioxan-2-one 9.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830710
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Zur cyclisierenden Carbonylierung von 3-Hydroxycarbohydroxamsäuren mit 1,1′-Carbonyldiimidazol1a) (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 219-225 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cyclic Carbonylation of 3-Hydroxycarbohydroxamic Acids with 1,1′-CarbonyldiimidazoleThe reaction of 3-hydroxycarbohydroxamic acids 3 with 1,1′-carbonyldiimidazole produces as a function of the substitution of 3 heterocycles of type 1, 4, and 5. In the presence of imidazole the 3-(2-hydroxyalkyl)-1,4,2-dioxazol-5-ones 1 undergo rearrangement into 2-oxazolidones 2.
    Notes: 3-Hydroxycarbohydroxamsäuren 3 reagieren mit 1,1′-Carbonyldiimidazol in Abhängigkeit von der Substitution des Säurerestes zu den Heterocyclen vom Typ 1, 4 und 5. Aus den 3-(2-Hydroxyalkyl)-1,4,2-dioxazol-5-onen 1 erhält man durch Imidazolkatalyse 2-Oxazolidone 2.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820204
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  • 3
    Electronic Resource
    Electronic Resource
    Zur Cyclisierung von Salicylsäureamiden und Salicylohydroxamsäuren mit 1,1′-Carbonyldiimidazol (1981)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1981 (1981), S. 1513-1514 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The Cyclisation of Salicylamides and Salicylohydroxamic Acids with 1,1′-CarbonyldiimidazoleCyclisation of salicylamides 1a, b and salicylohydroxamic acids 1c, d with 1,1′-carbonyldiimid-azole (2) causes formation of 2H-1,3-benzoxazine-2,4(3H)-diones 4a-d. In contrast to statements in the literature isoimides 3 or isoxazoles 5 could not be isolated.
    Notes: Salicylsäureamide 1a, b und Salicylohydroxamsäuren 1c, d cyclisieren mit 1,1′-Carbonyldiimid-azol (2) zu 2H-1,3-Benzoxazin-2,4(3H)-dionen 4a-d. Isoimide 3 oder Isoxazole 5 konnten entgegen Literaturangaben nicht isoliert werden.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198119810824
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  • 4
    Electronic Resource
    Electronic Resource
    3-(1-Hydroxyalkyl)-1,4,2-dioxazol-5-one und 3-Hydroxyoxazolidin-2,4-dione aus 2-Hydroxycarbohydroxamsäuren und 1,1′-Carbonyldiimidazol1a) (1982)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1982 (1982), S. 211-218 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 3-(1-Hydroxyalkyl)-1,4,2-dioxazol-5-ones and 3-Hydroxyoxazolidine-2,4-diones from 2-Hydroxycarbohydroxamic Acids and 1,1′-Carbonyldiimidazole1a)The reaction of 2-hydroxycarbohydroxamic acids 6 with 1,1′-carbonyldiimidazole produces 3-(1-hydroxyalkyl)-1,4,2-dioxazol-5-ones 7 and 3-hydroxyoxazolidine-2,4-diones 8. The formation of the heterocycles 7 and 8 depends largely on the substitution at C-2 of 6. Excess of imidazole causes rapid decomposition of 7 into carbonyl compound 9 and isocyanic acid, which yields the adduct 10 with imidazole. Benzylaminolysis of 7a gives 11 whereas the reaction of 7a with 3-chloroaniline produces the ureas 12 and 14 and benzophenone (9a). From the reaction of 7a with imidazole in a mole ratio of 1:1 the decomposition products 9a and 10 and 3-hydroxy-5,5-diphenyl-oxazolidine-2,4-dione (8a) are obtained.
    Notes: 2-Hydroxycarbohydroxamsäuren 6 reagieren mit 1,1′-Carbonyldiimidazol zu 3-(1-Hydroxyalkyl)-1,4,2-dioxazol-5-onen 7 und 3-Hydroxyoxazolidin-2,4-dionen 8, wobei die Cyclisierung in Richtung 7 und 8 durch die Substitution an C-2 von 6 bestimmt wird. In Gegenwart von überschüssigem Imidazol zerfallen die Heterocyclen 7 rasch in Carbonylverbindung 9 und Isocyansäure, die vom Imidazol unter Bildung von 10 gebunden wird. Während aus der Benzylaminolyse von 7a die O-Benzylcarbamoylbenzilohydroxamsäure (11) resultiert, führt die Reaktion von 7a mit 3-Chloranilin zu den Harnstoffen 12 und 14 sowie Benzophenon (9a). Aus der Umsetzung von 7a mit Imidazol im Molverhältnis 1:1 erhält man neben den Zerfallsprodukten 9a und 10 das 3-Hydroxy-5,5-diphenyloxazolidin-2,4-dion (8a).
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198219820203
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  • 5
    Electronic Resource
    Electronic Resource
    1,2-Oxazetidin-3-one aus (2-Thienyl)glycolohydroxamsäuren und 1,1′-Carbonyldiimidazol (1984)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1984 (1984), S. 894-899 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 1,2-Oxazetidin-3-ones from (2-Thienyl)glycolohydroxamic Acids and 1,1′-CarbonyldiimidazoleReaction of (2-thienyl)glycolohydroxamic acids 6 with 1,1′-carbonyldiimidazole yields 1,2-oxaze-tidin-3-ones 3B in high yields. The conversion of 6 into 3B proceeds via the intermediate 5B which can be isolated under suitable conditions.
    Notes: (2-Thienyl)glycolohydroxamsäuren 6 reagieren mit 1,1′-Carbonyldiimidazol in hohen Ausbeuten über die unter geeigneten Bedingungen isolierbare Zwischenstufe 5B zu 1,2-Oxazetidin-3-onen 3B.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198419840507
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