One-Pot Synthesis of Dihydropyrimidinones Using Polyaniline-Bismoclite Complex. A Facile and Reusable Catalyst for the Biginelli Reaction

Abstract

Polyaniline-bismoclite complex was used as an efficient catalyst for the three-component condensation reaction of an aldehyde, β-ketoester, and urea in ethanol to afford the dihydropyrimidinones in excellent yields. Furthermore, after completion of reaction the catalyst could be easily recovered and reused without affecting its activity.

polyaniline-bismoclite - reusable catalyst - dihydropyrimidinones - one-pot condensation - Biginelli reaction

References

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(a) Typical Procedure for the Preparation of Polyaniline-Bismoclite Complex (i)Preparation of polyaniline-sulfate salt: In a typical experiment, 10 mL of aniline was added to an aqueous solution (700 mL) containing H₂SO₄ (30 mL) in a 2 L-round-bottomed flask. The solution was kept under constant stirring at 5-10 °C. To this solution, sodium persulfate (23.8 g) in water (250 mL) was added during 15-20 min. The reaction was allowed to continue for 4 h. The precipitated polyaniline-sulfate salt was filtered, washed with water (5 L) followed by acetone (500 mL). (ii) Preparation of polyaniline base: The obtained polyaniline-sulfate salt was dispersed in an aqueous solution of NaOH (1 L, 1 N) and stirred for 12 h at ambient temperature. The solution was filtered and washed several times with water to remove the excess NaOH. The product (polyaniline base) was dried at 100 °C until a constant mass was reached. (iii) Preparation of polyaniline-bismoclite complex: Polyaniline base (5 g) prepared by the above method was added to acetone (500 mL) containing 0.1 M of BiCl₃. The solution was stirred for 4 h under an N₂ atmosphere at ambient temperature. The solution was filtered and washed with acetone (1 L). The powder was dried at 100 °C until a constant mass was reached.
(b) Properties of PANI-BC complex The PANI-BC complex possesses useful properties,
(i) number of dopant groups(bismoclite) per aniline unit in the polymer chain, i.e., x = 0.38; (ii) amount of bismoclite present in polyaniline salt (51.5%); (iii) conductivity (0.004 S/cm); (iv) pellet density (1.85 g/cm³) and particle size from SEM analysis (0.8-3 µm with core shell morphology).