Merz, Andreas and Meyer, Thomas (1999) A short and efficient synthesis of 3,4-dialkoxypyrroles. SYNTHESIS-STUTTGART (1). pp. 94-99. ISSN 0039-7881,
Full text not available from this repository. (Request a copy)Abstract
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 bis-alkylated 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.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | CROWN; dihydroxydihydrofuran; tetraalkoxyfurans; O,N-exchange; N-benzyl cleavage; N-allyl cleavage |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 06 Dec 2022 07:22 |
| Last Modified: | 06 Dec 2022 07:22 |
| URI: | https://pred.uni-regensburg.de/id/eprint/48743 |
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