Abstract
A one-pot synthesis of 2,3-disubstituted 4-(3H )-quinazolinones has been carried out efficiently by the three-component coupling of isatoic anhydride/anthranilic acid, orthoesters, and amines in the presence of Nafion-H (a perfluorinated resin-supported sulfonic acid) as a heterogeneous catalyst. The reaction occurred within a few minutes under solvent-free microwave irradiation conditions to afford the products in good yields. The catalyst was recovered and recycled.
Key words
quinazolin-4-(3H )-ones - Nafion-H - one-pot reaction - microwave irradiation
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General Procedure: A mixture of isatoic anhydride (1.8 mmol) or anthranilic acid (1.8 mmol), triethyl orthoester (1.8 mmol), aromatic aniline (1.8 mmol), and a catalytic amount of Nafion-H was irradiated in a domestic microwave oven at 800 W in an open tube for 2-6 min. After completion of the reaction the reaction mixture was allowed to cool to ambient temperature, dissolved in EtOAc, and the catalyst was separated by filtration. The organic layer was dried with Na2 SO4 and concentrated. The solid was passed through a silica gel column (n -hexane-CHCl3 , 1:1) to furnish the title compound in sufficiently pure form.
