4-氨基-5-氰基-6-烷胺基吡啶衍生物的合成与生物活性
收稿日期: 2015-03-18
修回日期: 2015-05-21
网络出版日期: 2015-06-12
基金资助
国家自然科学基金(Nos. 21172090, 31000867)、教育部创新团队项目部分(No. IRT0953)资助项目.
Synthesis and Biological Activity of 4-Amino-5-cyano-6-alkylamino Pyridine Derivatives
Received date: 2015-03-18
Revised date: 2015-05-21
Online published: 2015-06-12
Supported by
Project supported by the National Program on Key Basic Research Project (973 Program. No. 2010CB126100), the National Natural Science Fundation of China (No. 21172090; 31000867) and the Program for Changjiang Scholars and Innovatives Research Team in University (No. IRT0953).
采用六水合硝酸锌作催化剂、少量的乙醇钠为助催化剂, 使用无水乙醇作为溶剂, 将2-氰基-3-烷胺基-3-氨基-丙烯腈(N,N-缩醛)与β-二羰基化合物一步关环生成了一系列目标化合物4-氨基-5-氰基-6-烷胺基吡啶衍生物. 通过1H NMR, IR, EI-MS, 元素分析等方法对所合成的化合物进行了结构表征. 代表化合物2-甲基-4-氨基-5-氰基-6-乙醇胺基-3-乙氧羰基吡啶经单晶X衍射证实了结构. 对合成的多取代吡啶衍生物化合物作了初步的农药活性测试, 测试结果表明: 所合成的多取代吡啶衍生物部分化合物表现出较好的杀菌活性, 同时也对油菜和稗草具有一定的除草活性.
刘建超 , 任青云 , 贺红武 . 4-氨基-5-氰基-6-烷胺基吡啶衍生物的合成与生物活性[J]. 有机化学, 2015 , 35(10) : 2212 -2217 . DOI: 10.6023/cjoc201503028
A series of new 4-amino-5-cyano-6-alkylamino pyridine derivatives have been designed and synthesized from 2-cyano-3-alkylamino-3-amino acrylonitriles and β-dicarbonyl compounds using Zn(NO3)2 and C2H5ONa as catalysts in anhydrous ethanol. The structures of target compounds have been confirmed by 1H NMR, EI-MS, IR spectroscopy and elemental analysis. The structure of 2-methyl-4-amino-5-cyano-6-(2-hydroxyl ethylamino)-nicotinic ethyl ester has been determined by single crystal X-ray diffraction. The results of preliminary bioassay indicated that some compounds possess potential good fungicidal activities at a dosage of 5.0×10-5 g/mL, and some compounds also possess moderate herbicidal activities against the Rape and Barnyard grass.
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