Highly efficient solvent-free synthesis of quinazolin-4(3H)-ones and 2,3-dihydroquinazolin-4(1H)-ones using tetrabutylammonium bromide as novel ionic liquid catalyst |
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Authors: | A. Davoodnia S. Allameh A.R. Fakhari N. Tavakoli-Hoseini |
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Affiliation: | Department of Chemistry, Faculty of Sciences, Islamic Azad University, Mashhad Branch, Mashhad 91735-413, Iran |
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Abstract: | A simple and efficient procedure for the synthesis of 2-arylquinazolin-4(3H)-ones has been developed through cyclocondensation of 2-aminobenzamide with aromatic aldehydes using tetrabutylammonium bromide (TBAB) as novel neutral ionic liquid catalyst in the presence of copper (Ⅱ) chloride (CuCl2) as oxidizing agent under solvent-free conditions at 100 ℃. In the absence of CuCl2 and under a nitrogen atmosphere, the unoxidized intermediates, 2-aryl-2,3-dihydroquinazolin-4(1H)-ones, were isolated.Treatment of these intermediates with CuCl2 in TBAB media gave the oxidized products 2-arylquinazolin-4(3H)-ones. On the other hand, cyclocondensation of 2-aminobenzamide with aromatic aldehydes in TBAB under microwave irradiation directly gave 2-arylquinazolin-4(3H)-ones. |
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Keywords: | Quinazolinones Aromatic aldehydes Tetrabutylammonium bromide (TBAB) Microwave irradiation |
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