220280-01-3Relevant academic research and scientific papers
A short and efficient synthesis of 3,4-dialkoxypyrroles
Merz, Andreas,Meyer, Thomas
, p. 94 - 99 (2007/10/03)
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.
