Microwave-assisted polystyrene sulfonate-catalyzed synthesis of novel pyrroles
© Cárdenas et al.; licensee Springer. 2012
Received: 3 January 2012
Accepted: 20 April 2012
Published: 22 June 2012
Pyrroles are widely distributed in nature and important biologically active molecules. The reaction of amines with 2,5-dimethoxytetrahydrofuran is a promising pathway for the synthesis of pharmacologically active pyrroles under microwave irradiation.
Microwave-induced polystyrenesulfonate-catalyzed synthesis of pyrroles from amines and 2,5-diemthoxytetrahydrofuran has been accomplished with excellent yield. This method produces pyrroles with polyaromatic amines.
The present procedure for the synthesis of N-aromatic substituted pyrroles will find useful application in the area of pharmacologically active molecules.
KeywordsPyrrole Polystyrene sulfonate Microwave 2,5-dimethoxytetrahydrofuran
Polystyrene sulfonate-catalyzed simple synthesis of N -substituted pyrroles under microwave irradiation (300 W, 60°C) following Figure 1
Yield (%) a
FT-IR spectra were registered on a Bruker IFS 55 Equinox FTIR spectrophotometer (Bruker Corporation, Billerica, MA, USA) as KBr discs.1 H-NMR (600 MHz) and13 C-NMR (150 MHz) spectra were obtained at room temperature with Bruker-600 equipment (Bruker Corporation) using TMS as internal standard and CDCl3 as solvent. Analytical grade chemicals (Sigma-Aldrich Corporation, St. Louis, MO, USA) were used throughout the project. Deionized water was used for the preparation of all aqueous solutions.
Results and discussion
Polystyrene sulfonate-catalyzed simple synthesis of N -substituted pyrroles at room temperature following Figure 1
Yield (%) a
General procedure for the synthesis of pyrroles (3)
Amine (1.0 mmol), 2, 5-dimethoxytetrahydrofuran (1.2 mmol) and polystyrene sulfonate (18 wt% solution in water) in ethanol/water (1:1) mixture was stirred at room temperature, and the progress of the reaction was monitored by TLC every 30 min. After completion of the reaction (Table 2), the reaction mixture was basified with saturated aqueous sodium bicarbonate solution and extracted with dichloromethane. The organic layer was then washed with brine, dried with sodium sulfate and evaporated to isolate the pure product.
Alternatively, amine (1.0 mmol), 2, 5-dimethoxytetrahydrofuran (1.2 mmol) and polystyrene sulfonate (18 wt% solution in water) in ethanol/water (1:1) were irradiated in an automated microwave oven (CEM Corporation, Matthews City, NC, USA). The reaction was monitored by TLC every 5 min. Depending upon the nature of the amines, the reaction was completed in different time. The result of the procedure was shown in Table 1. All the products have demonstrated satisfactory spectral and mp data with our reported compounds .
A new and simple method for the synthesis of N-substituted pyrroles in aqueous solution has been investigated with success. Based on our previous studies in this series, the compounds as reported herein may demonstrate anticancer activities.
We gratefully acknowledge the funding support from the Kleberg Foundation, Texas.
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