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有机化学
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有机化学 ›› 2007, Vol. 27 ›› Issue (02): 279-284. 上一篇    下一篇

研究简报

O,O'-二烷基-α-(取代苯并噻唑-2-基)氨基-(取代苯基甲基)膦酸酯的合成与抗烟草花叶病毒活性

王伟，张国平，宋宝安*，汪华
金林红，胡德禹，杨松   

  1. (贵州大学精细化工研究开发中心 教育部绿色农药和农业生物工程重点实验室 贵阳 550025)
  • 收稿日期:2006-02-20 修回日期:2006-06-20 发布日期:2007-01-30
  • 通讯作者: 宋宝安

Synthesis and Anti-Tobacco Mosaic Virus Activity of O,O'-Dialkyl- α-(substituted benzothia-zol-2-yl)amino-(substituted phenylmethyl)phosphonate

WANG Wei, ZHANG Guo-Ping, SONG Bao-An*, WANG Hua
JIN Lin-Hong, HU De-Yu, YANG Song   

  1. (Key Laboratory of Green Pesticide and Agricultural Bioengineering of Ministry of Education, Research and Development
    Center of Fine Chemicals, Guizhou University, Guiyang 550025)
  • Received:2006-02-20 Revised:2006-06-20 Published:2007-01-30
  • Contact: SONG Bao-An

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采用无溶剂无催化剂合成方法, 分别进行了以O,O'-二烷基亚磷酸酯、3,4,5-三甲氧基苯甲醛、2-氨基取代苯并噻唑为原料的类Mannich一锅法合成反应研究, 经合成筛选, 优选出控制反应温度100 ℃, 无溶剂、无催化剂加热反应120 min的合成方法, 实验结果表明该方法经济、简便、对环境友好. 经元素分析, IR, 1H NMR, 13C NMR对所合成的化合物进行了结构确认和表征. 培养并测定了化合物4a的晶体结构. 初步生物活性测试表明, 化合物具有一定的抗烟草花叶病毒活性.

关键词: α-氨基膦酸酯, 抗烟草花叶病毒活性, 苯并噻唑, 合成, 无溶剂无催化剂

The Mannich-type addition of O,O'-dialkyphosphite to 3,4,5-trimethoxybenzaldehyde and 2-aminobenzothiazole was carried out in one pot by means of adopting solvent-catalyst free condition. The optimized condition is at 100 ℃ and 120 min without catalyst and solvent, which is economic, convenient, high yields and environment-friendly. Their structures were clearly established by elemental analysis, IR, 1H NMR and 13C NMR spectra. Single crystals of 4a have been obtained and determined. The bioassay of some compounds showed that they have moderate anti-tobacco mosaic virus (TMV) activity.

Key words: synthesis, solvent-catalyst free, anti-TMV activity, benzothiazole moiety, α-aminophosphonate