Synthesis of Functionalized Pyrroles by Reaction of 3,4‐Diacetylhexane‐2,5‐dione with Primary Amines in Water

Abstract

3,4‐Diacetylhexane‐2,5‐dione (tetra‐acetylethane) undergoes a complex reaction with primary amines in boiling water to produce N‐alkyl‐3‐acetyl‐2,5‐dimethylpyrroles, together with small quantities of N‐alkyl‐3,4‐diacetyl‐2,5‐dimethylpyrroles and 2,5‐dimethyl‐1H‐pyrrol‐3‐yl‐vinyl‐acetamides. When the reaction was carried out in methanol at room temperature, the yields of the latter products increased.

Keywords:

• cyclization
• 3,4‐diacetylhexane‐2,5‐dione
• N‐heterocycles
• Paal–Knorr
• primary amine
• pyrrole synthesis
• water