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  • 1
    Electronic Resource
    Electronic Resource
    Springer
    Monatshefte für Chemie 128 (1997), S. 79-83 
    ISSN: 1434-4475
    Keywords: Allylic rearrangement ; Tetrabromoacetone ; 9,10-Dimethoxy-9,10-propanoanthracen-12-ones ; Ring contraction ; Molecular mechanics calculations (MM2)
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung UnterFavorskii-Bedingungen (MeOH/KOH, 60°C) entstehen auscis- undtrans-11,13-Dibrom-9,10-dimethoxy-9,10-propanoanthracen-12-on derFavorskii-Ester5a und das α-Keto-Acetal5b in 46% Gesamtausbeute. Fast alle Reaktionen ergeben ein einziges Isomeres, von dem mittels molekularmechanischer Berechnungen gezeigt werden konnte, daß es sich dabei um das energetisch günstigere Produkt handelt.
    Notes: Summary Submittingcis- andtrans-11,13-dibromo-9,10-dimethoxy-9,10-propanoanthracen-12-one (4a,b) toFavorskii conditions (MeOH/KOH, 60°C) afforded theFavorskii ester5a and the α-keto acetal5b in 46% overall yield. Almost all reactions resulted in the formation of a single isomer which could be shown to be the most favored one by molecular mechanics calculations (MM2).
    Type of Medium: Electronic Resource
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  • 2
    ISSN: 1434-4475
    Keywords: Pyrimidothiazolobenzimidazole ; Chlorination ; Nucleophilic substitution ; Condensation ; Pharmacological interest
    Source: Springer Online Journal Archives 1860-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Zusammenfassung 4-Chlor-2-methylpyrimidino[4′,5′:4,5]thiazolo[3,2-a]benzimidazol (3) wurde durch Chlorierung von2, welches auch direkt zu 2-Methylpyrimidino[4′,5′:5,4]thiazolo[3,2-a]-benzimidazol-4-thiol (4) umgesetzt werden kann, hergestellt. Nucleophile Substitution von3 mit Alkoholen, Phenolen, primären Aminen, sekundären Aminen, Natriumazid und Mercaptoessigsäure ergab die entsprechenden Derivate. Das Thiolderivat4 wurde mit Alkyl/Alkarylhalogeniden, Phenacylbromidderivaten, Bromaceton, Chloraniliden, Brommalonsäureester und Bromessigsäureethylester zu potentiell pharmakologisch interessanten Verbindungen umgesetzt.
    Notes: Summary 4-Chloro-2-methylpyrimidino[4′,5′:4,5]thiazolo[3,2-a]benzimidazole (3) was prepared by chlorination of2 which could also be converted directly to 2-methylpyrimidino[4′,5′:4,5]-thiazolo[3,2-a]benzimidazol-4-thiol (4). Nucleophilic substitution of3 with alcohols, phenols, primary amines, secondary amines, sodium azide, and mercaptoacetic acid gave the corresponding derivatives. The thiol derivative4 was reacted with alkyl/aralkyl halides, phenacyl bromide derivatives, bromoacetone, chloroanilides, bromomalonic ester, and ethyl bromoacetate to afford compounds of potential pharmacological interest.
    Type of Medium: Electronic Resource
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