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Synthesis 1999; 1999(1): 94-99
DOI: 10.1055/s-1999-3687
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A Short and Efficient Synthesis of 3,4-Dialkoxypyrroles

Andreas Merz* , Thomas Meyer
  • *Institut für Organische Chemie der Universität Regensburg, D-93040 Regensburg, Germany; Fax +49(9 41)9 43 41 21; E-mail: Merz@chemie.uni-regensburg.de
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Publikationsdatum:
31. Dezember 1999 (online)

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3,4-Dialkoxypyrroles are obtained in four steps from commercially available 2,5-dimethoxy-2,5-dihydrofuran (1). The dihydrofuran 1 is first oxidized by KMnO4 to the diol 2 which is bisalkylated to 3a-d. Reaction of the in situ generated dialdehydes with a primary amine affords the N-substituted dialkoxypyrroles 4a-m. N-Benzyl-3,4-dialkoxypyrroles and N-allyl-dialkoxypyrroles are cleaved by sodium in liquid ammonia affording N-unsubstituted dialkoxypyrroles 5a-c in good overall yield.

dihydroxydihydrofuran - tetraalkoxyfurans - O,N-exchange - N-benzyl cleavage - N-allyl cleavage