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Efficient solid-phase synthesis of quinazoline-2,4-diones with various substituents on aromatic rings

✍ Scribed by Tatsuya Okuzumi; Eiji Nakanishi; Takashi Tsuji; Shingo Makino

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
200 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

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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