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Synthesis 1995; 1995(10): 1295-1299
DOI: 10.1055/s-1995-4082
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A New Versatile Synthesis of Xanthines with Variable Substituents in the 1-, 3-, 7- and 8-Positions

Christa E. Müller* , Jesús Sandoval-Ramírez
  • *Institut für Pharmazie und Lebensmittelchemie, Pharmazeutische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany, E-mail mueller@pharmazie.uni-wuerzburg.de
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Publikationsdatum:
31. Dezember 2000 (online)

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A new convenient procedure for the synthesis of a wide range of xanthines has been developed starting from 3-substituted 6-aminouracils. Nitrosation and reduction yields the corresponding 5,6-diaminouracils, which are condensed with carboxylic acids. The resulting amides can be selectively alkylated at the uracil ring nitrogen N-1 (corresponding to xanthine N-3) under mild conditions. Ring closure and, if desired, alkylation at the 7-position, yields di-, tri-, or tetrasubstituted xanthines in high yields. Sensitive substituents, such as prop-2-ynyl, can be introduced in the 1-position. Variation of the 3-substituent is considerably facilitated in comparison with the standard procedure for the preparation of xanthines.

xanthine - xanthine synthesis - uracil - selective alkylation - propargylxanthines