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  • Inorganic Chemistry  (2)
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  • 1
    Electronic Resource
    Electronic Resource
    Notizen Reaktionsfähigkeit von Aporphin-Alkaloiden gegenüber Formaldehyd (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 3737-3739 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactivity of Aporphine Alkaloids against FormaldehydeGlaucine (1) reacts with formaldehyde in neutral medium to form 4. As an intermediate 5 is obtained which has a weak enamine chracter against formaldehyde. Bracteoline (2) can be obtained after hydrobromic acid/acetic acid hydrolysis of 1. Treatment of 2 with formaldehyde in alkaline media leads to 3, which on heating near the melting point (about 150°C) is converted into 6. This is a new route for the synthesis of thalphenine-type alkaloids.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791121122
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  • 2
    Electronic Resource
    Electronic Resource
    Amidomethylierung, Hydroxymethylierung und Formylierung des Glaucins (1978)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 111 (1978), S. 554-558 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Amidomethylation, Hydroxymethylation and Formylation of GlaucineGlaucine (1) reacts with N-(hydroxymethyl)acetamide in acidic media to form 3-(acetamidomethyl)glaucine (2) and 3,11-bis(acetamidomethyl)glaucine (3). Treatment with formaldehyde under similar conditions leads to 3-(hydroxymethyl)glaucine (4). 4 can be oxidized to yield 3-formylglaucine (6) which undergoes Dakin's rearrangement, and with CH2N2 gives thalicsimidine (purpureine, 8). Vilsmeyer reaction with 1 leads to 9.
    Notes: Glaucin (1) wird beim Erwärmen in saurem Medium mit N-(Hydroxymethyl)acetamid in 3-(Acetamidomethyl)glaucin (2) und 3,11-Bis(acetamidomethyl)glaucin (3) umgewandelt. Unter den gleichen Bedingungen wird mit Formaldehyd 3-(Hydroxymethyl)glaucin (4) gebildet. K2Cr2O7 oxidiert 4 zu 3-Formylglaucin (6), das einer Dakin-Umwandlung unterliegt und mit CH2N2 zu Thalicsimidin (Purpurein, 8) führt. 1-[2-(N-Methylformamido)ethyl]-3,4,6,7-tetramethoxyphenanthren (9) entsteht durch Vilsmeyer-Reaktion aus 1.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19781110214
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