Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (5): 1015-1020.DOI: 10.6023/cjoc201311046 Previous Articles     Next Articles



杨绪红a, 王翔b, 吴鸣虎a   

  1. a 湖北科技学院核技术与化学生物学院 咸宁 437100;
    b 凯里学院化学与材料工程学院 凯里 556011
  • 收稿日期:2013-11-29 修回日期:2013-12-19 发布日期:2014-01-03
  • 通讯作者: 吴鸣虎
  • 基金资助:

    贵州省自然科学联合基金(No. LKK[2013]03)资助项目.

Synthesis and Biological Properties of 3-(2-Hydroxyethyl)-2-(phenylamino)quinazolin-4(3H)-ones

Yang Xuhonga, Wang Xiangb, Wu Minghua   

  1. a Faculty of Nuclear Technology & Chemistry and Biology, Hubei University of Science and Technology, Xianning 437100;
    b College of Chemistry and Materials Engineering, Kaili University, Kaili 556011
  • Received:2013-11-29 Revised:2013-12-19 Published:2014-01-03
  • Supported by:

    Project supported by the Natural Science Mutual Funds of Guizhou Province (No. LKK[2013]03).

Key intermediate β-ethoxycarbonyl iminophosphorance (4), which was prepared from starting material substituted 2-aminobenzoic acid (1), was reacted with aryl isocyanates, ethanolamine by a three-component tandem aza-Wittig reaction to obtain a series of 2-arylamino-3-hydroxyethyl-4(3H)-quinazolinone derivatives 6. The structures of the target products were confirmed by IR, 1H NMR, MS and elemental analysis. The antibacterial activities of compounds 6 in vitro against tobacco bacterial wilt were further tested. The bioassay of the compounds 6 showed that the inhibitory activities of all the compounds were lower than the reference drug thiediazole copper. However, the antibacterial activity was significantly enhanced when the parent quinazolinone rings of the compounds 6 are substituted. Thus it can be seen that decoration of the parent quinazolinone ring of the compounds 6 can be regard as a kind of effective way of improving their biological property.

Key words: quinazolin-4(3H)-one, aza-Wittig reaction, synthesis, bactericidal activity