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New synthetic approach to 8-allyltheophylline

Ein neuer synthetischer Zugang zu 8-Allyltheophyllin

  • Organische Chemie Und Biochemie
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Summary

The synthesis of 8-allyltheophylline (8) from 5,6-diamino-1,3-dimethyluracil (1) and 3-butenoic acid byTraube's methodvia 6-amino-5-(3-butenoylamino)-1,3-dimethyluracil (2) failed because an attempted alkaline cyclization of the intermediate2 afforded (E)-8-(1-propenyl)-theophylline (3) under rearrangement of the terminal C=C bond. Therefore, the cyclodehydratation of 6-(3-butenylamino)-5-nitroso-1,3-dimethyluracil (7), available from 6-chloro-1,3-dimethyluracil (5)via 6-(3-butenylamino) derivative6 has to be used for obtaining the required product8.

Zusammenfassung

8-Allyltheophyllin (8) kann nicht mittels derTraube-Synthese aus 5,6-Diamino-1,3-dimethyluracil und 3-Butensäurevia 6-Amino-5-(3-butenoylamino)-1,3-dimethyluracil (2) hergestellt werden, wei bei der alkalischen Cyclisierung des Zwischenproduktes2 Umlagerung der terminalen C=C-Doppelbindung unter Bildung von (E)-8-(1-Propenyl)theophyllin (3) erfolgt. Zur Darstellung der Verbindung8 muss man daher die Dehydratationscyclisierung von 6-(3-Butenylamino)-5-nitroso-1,3-dimethyluracil (7) anwenden. Letzteres ist aus 6-Chloro-1,3-dimethyluracil über das 6-(3-Butenylamino)-Derivat6 zugänglich.

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Authors and Affiliations

  1. Institute of Chemistry, Slovak Academy of Sciences, SK-84238, Bratislava, Slovakia

    A. Rybár, J. Alföldi & I. Šmondrková

Authors
  1. A. Rybár
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  2. J. Alföldi
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  3. I. Šmondrková
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Rybár, A., Alföldi, J. & Šmondrková, I. New synthetic approach to 8-allyltheophylline. Monatsh Chem 125, 565–570 (1994). https://doi.org/10.1007/BF00811849

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  • DOI: https://doi.org/10.1007/BF00811849

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