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  • 1
    Electronic Resource
    Electronic Resource
    Reductive Transformations of 6H-1,2-Oxazines with Hydride Reagents: Formation of Aziridines and 3-Hydroxyalkylated 1,2-oxazines (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1155-1157 
    Details
    ISSN: 0170-2041
    Keywords: 1,2-Oxazines ; Aziridines ; Hydride reagents ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 6H-1,2-Oxazines 1 and 3 are converted into aziridines 2 and 4, respectively, by reduction with LiAlH4. Reduction of 1,2-oxazine 5 lacking the 6-alkoxy substituent leads to phenyl ketone 6, 6-Alkoxy-substituted 1,2-oxazine-3-carboxylates 7, 9, and 11 are reduced with NaBH4 to give the corresponding 3-hydroxymethylated compounds 8, 10, and 12 in good yields.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301186
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  • 2
    Electronic Resource
    Electronic Resource
    6-Siloxy-Substituted 5,6-Dihydro-4H-1,2-oxazines as Key Building Blocks for Natural Products (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 709-714 
    Details
    ISSN: 0170-2041
    Keywords: Pyrenophorin ; (Z)-Jasmone ; 1,2-Oxazine ; Pheromones ; Pyrroles ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Methyl (E)-5-bromo-4-oxo-2-pentenoate (6) and the corresponding oxime 5 were prepared in high yields by starting from methyl levulinate (3). The novel nitrosoalkene 8, generated in situ from oxime 5, smoothly added to silyl enol ether 7 to give 1,2-oxazine 9 and nitrone 10 as byproduct. Methods are described transforming intermediate 9 into unsaturated diketo ester 11, or oximes 13, 15, and 18, which may serve as precursors of pyrenophorin. Reductive ring cleavage of 1,2-oxazine 9 with Raney nickel efficiently afforded the saturated diketo ester 19. Its intramolecular aldol reaction gave cyclopentenone derivative 20, which is a known precursor of (Z)-jasmone. Cycloaddition of methyl α-nitrosoacrylate to silyl enol ether 22 provided 1,2-oxazine 23. This compound was directly converted into the ant-trail pheromone 24 by hexacarbonylmolybdenum-promoted ring contraction.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201119
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    Paper (German National Licenses)
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