反-2,3,6(8)-三取代-1,3-苯并噁嗪类化合物的立体选择性合成、晶体结构与杀菌活性  

Stereoselective Synthesis, Crystal Structure and Fungicidal Activity of trans-2,3,6(8)-Trisubstituted-1,3-benzoxazines

作　　者：唐子龙[1,2] 夏赞稳[1] 李新兴[1] 

机构地区：[1]湖南科技大学理论有机化学与功能分子教育部重点实验室,湘潭411201 [2]湖南科技大学化学化工学院,湘潭411201

出　　处：《有机化学》2016年第3期590-595,共6页Chinese Journal of Organic Chemistry

基　　金：国家自然科学基金(Nos.21042011;21372070);国家科技计划支撑子项目(No.2011BAE06B01);湖南省高校创新平台开放基金(No.13k089)资助项目~~

摘　　要：在TMSCl的催化作用下,2-芳氨基甲基苯酚和取代苯甲醛经N,O-缩醛反应合成了一系列新型反-2,3,6(8)-三取代-1,3-苯并噁嗪类化合物,收率为38%~80%.该反应呈现出高度反式选择性.产物结构用1H NMR,13C NMR,IR和元素分析等进行了表征.对目标化合物进行了杀菌活性测试,在测试浓度下,大部分显示中等至良好的活性.其中化合物5d和5f在浓度为50?g/m L时抗稻瘟病菌的活性达78.6%.A series of novel trans-2,3,6（8）-trisubstituted-1,3-benzoxazines were prepared in yields of 38%~80% by reactions of 2-arylaminomethyl phenols with various substituted benzaldehydes in the presence of TMSCl. The reaction showed high trans selectivity. The structures of all the target products were characterized by ~1H NMR, ^（13）C NMR, IR and elemental analysis. The fungicidal activities of the prepared compounds were investigated, most of which showed moderate to good activity, compounds 5d and 5f showed growth inhibition of 78.6% against M. oryzae at 50 mg/m L.

关 键 词：2 3 6(8)-三取代-1 3-苯并噁嗪 合成 立体选择性 杀菌活性 

分 类 号：O626[理学—有机化学]