Efficient solid-phase synthesis of quinazoline-2,4-diones with various substituents on aromatic rings |
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Institution: | 1. Nonwovens Research Group, School of Design, University of Leeds, UK;2. Advanced Materials Engineering, Polymer IRC Labs, Faculty of Engineering & Informatics, University of Bradford, UK;3. Arvind-OG Nonwovens, Ahmedabad, India;4. Institut für Textilchemie und Textilphysik, Universität Innsbruck, Austria |
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Abstract: | We have developed a method for the solid-phase synthesis of quinazoline-2,4-diones with various substituents on the aromatic ring. Although there have been numerous reports of the solid-phase synthesis of quinazoline-2,4-diones, they were not applicable to the synthesis of the quinazoline-2,4-diones with electron-withdrawing substituents on the aromatic ring. Considering the poor nucleophilicity of the amino group of anthranilic acids, coupling of anthranilic acids to solid-supported amines was investigated without protecting the amino group. Various anthranilamides were prepared using anthranilic acids with electron-withdrawing substituents because a wide range of anthranilic acids are commercially available. These anthranilamides were successfully cyclized with carbonyldiimidazole to give quinazoline-2,4-diones with high purity. |
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