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

被引：17

作者：

Okuzumi, T ^{[1
]}

Nakanishi, E ^{[1
]}

Tsuji, T ^{[1
]}

Makino, S ^{[1
]}

机构：

[1] Ajinomoto Co Inc, Pharmaceut Res Labs, Kawasaki Ku, Kawasaki, Kanagawa 2108681, Japan

来源：

TETRAHEDRON | 2003年 / 59卷 / 29期

关键词：

solid-phase synthesis; quinazoline-2,4-dione; anthranilic acid; heterocycle;

D O I：

10.1016/S0040-4020(03)00729-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：5603 / 5608

页数：6

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