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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 44, 2014 - Issue 9
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Original Articles

Paal–Knorr Pyrrole Synthesis in Water

, &
Pages 1323-1332 | Received 12 Sep 2013, Published online: 28 Mar 2014
 

Abstract

Water was a suitable medium for Paal–Knorr pyrrole cyclocondensation. Hexa-2,5-dione was reacted with several aliphatic and aromatic primary amines, affording N-substituted 2,5-dimethyl pyrrole derivatives in good to excellent yields. An efficient, green method using water either as environmentally friendly solvent or catalyst was presented.

GRAPHICAL ABSTRACT

Notes

Note: Reaction conditions: amine (10 mmol), 2,5-hexadione (10 mmol), 5 mL water, 15 min, 100 °C.

a Amine (5 mmol), 2,5-hexadione (10 mmol), 5 mL water, 15 min, 100 °C.

b Amine (3.3 mmol), 2,5-hexadione (10 mmol), 5 mL water, 15 min, 100 °C.

n.o., not observed.

Note: Reaction conditions: Aniline (10 mmol), 2,5-hexzadione (10mmol), solvent (5mL), 15min.

Note: Reaction conditions: Benzylamine (10mmol), 2,5-hexzadione (10mmol), solvent (5mL), 15min.

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