Polystyrenesulfonate-catalyzed synthesis of novel pyrroles through Paal-Knorr reaction
© Banik et al; licensee Springer. 2012
Received: 22 November 2011
Accepted: 27 March 2012
Published: 27 March 2012
The classical Paal-Knorr reaction is one of the simplest and most economical methods for the synthesis of biologically important and pharmacologically useful pyrrole derivatives.
Polystyrenesulfonate-catalyzed simple synthesis of substituted pyrroles following Paal-Knorr reaction has been accomplished with an excellent yield in aqueous solution. This method also produces pyrroles with multicyclic polyaromatic amines.
The present procedure for the synthesis of N-polyaromatic substituted pyrroles will find application in the synthesis of potent biologically active molecules.
Results and discussion
In conclusion, a new procedure for the synthesis of N-substituted pyrroles has been developed. Because of the simplicity of the procedure, products can be isolated very easily. The compounds reported herein will be tested against a number of cancer cells in vitro. This reaction will be applicable to the synthesis of various organic compounds of medicinal interests.
FT-IR spectra were registered on a Bruker IFS 55 Equinox FTIR spectrophotometer as KBr discs. 1H NMR (600 MHz) and 13C-NMR (150 MHz) spectra were obtained at room temperature with Bruker-600 equipment using TMS as internal standard and CDCl3 as solvent. Analytical grade chemicals (Sigma-Aldrich Corporation) were used throughout the project. Deionized water was used for the preparation of all aqueous solutions.
General procedure for the synthesis of pyrroles (3)
Amine (1.0 mmol), 2,5-hexanedione (1.2 mmol) and polystyrene sulfonate (18 wt. % solution in water) in water/ethanol (1:1) mixture was stirred at room temperature as specified in Table 1 and the progress of the reaction was monitored by TLC every 30 min. After completion of the reaction (Table 1) the reaction mixture was basified with aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic layer was then washed with brine, dried with sodium sulphate and evaporated to isolate the pure product.
MB is a high school research participant; BM is an undergraduate research participant and AR is a graduate student.
We gratefully acknowledged the funding support from the Kleberg Foundation, Texas.
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