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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (11): 1853-1857. 上一篇    下一篇

研究简报

2-烷(芳)氧基苯并呋喃并[3,2-d]嘧啶-4(3H)-酮衍生物的合成及杀菌活性

胡扬根*   徐靖   陈小保 屈永年   

  1. (郧阳医学院医学化学研究所 十堰 442000)
  • 收稿日期:2009-05-11 修回日期:2009-07-02 发布日期:2009-10-09
  • 通讯作者: 胡扬根 E-mail:huyangg111@yahoo.com.cn

Synthesis and Fungicidal Activity of 2-Alkoxy(aryloxy)-benzofuro- [3,2-d]pyrimidin-4(3H)-one Derivatives

Hu, Yanggen*   Xu, Jing Chen,    Xiaobao    Qu, Yongnian   

  1. (Institute of Medicinal Chemistry, Yunyang Medical College, Shiyan 442000)
  • Received:2009-05-11 Revised:2009-07-02 Published:2009-10-09

PDF

1329

被引次数

6

应用膦亚胺3与芳基异氰酸酯的氮杂Wittig反应, 生成碳二亚胺4, 4再分别与酚、醇作用, 在碳酸钾或醇钠催化下关环, 以72%～88%的产率合成了2-烷(芳)氧基取代-苯并呋喃并[3,2-d]嘧啶-4(3H)-酮衍生物5和6, 其结构经IR, 1H NMR, MS和元素分析证实. 初步生物活性测试表明该类化合物表现出温和的杀菌活性. 如5f在50 mg/L浓度时, 对黄瓜灰霉菌的抑制率为55%.

关键词: 苯并呋喃并[3,2-d]嘧啶-4(3H)-酮, aza-Wittig反应, 碳二亚胺, 杀菌活性

The aza-Wittig reaction of iminophosphorane 3 with aromatic isocyanates gave carbodiimides 4, which were allowed to react further with various phenols and alcohols in the presence of a catalytic amount of solid potassium carbonate or sodium ethoxide to give 2-alkoxy(aryloxy)-benzofuro[3,2-d]pyrimidin- 4(3H)-ones in 72%～88% yields. Their structures were confirmed by 1H NMR, MS, IR and elemental analysis. The preliminary bioassays indicated that these compounds possessed moderate fungicidal activities against six kinds of fungi at a concentration of 50 mg/L.

Key words: benzofuro[3,2-d]pyrimidin-4(3H)-one, aza-Wittig reaction, carbodiimide, fungicidal activity