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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (07): 1129-1132. 上一篇    下一篇

研究简报

区域和立体选择性合成新型螺羟吲哚类化合物

李筱芳a,b; 于贤勇a; 冯亚青*,b   

  1. (a湖南科技大学理论化学与分子模拟省部共建教育部重点实验室
    分子构效关系湖南省普通高等学校重点实验室 湘潭 411201)
    (b天津大学化工学院应用化学系 天津 300072)
  • 收稿日期:2008-09-09 修回日期:2008-12-09 发布日期:2009-07-22
  • 通讯作者: 冯亚青

Regio- and Stereo-selective Synthesis of Novel Spirooxindole Compounds

Li, Xiaofang a,b; Yu, Xianyong a ; Feng, Yaqing*,b   

  1. (a Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, Hunan University of Science and Technology, Xiangtan 411201)
    (b School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072)
  • Received:2008-09-09 Revised:2008-12-09 Published:2009-07-22
  • Contact: Feng, Yaqing

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被引次数

4 | 1

2-芳亚甲基苯并[4,5]咪唑并[2,1-b]噻唑-3-酮与甲亚胺叶立德(经靛红与肌氨酸反应在线生成)进行l,3-偶极环加成反应, 合成了8个新的螺羟吲哚类化合物. 采用元素分析, NMR, IR, 质谱以及X射线单晶衍射等多种谱学技术对产物进行详细表征, 而产物的晶体结构表明了此类反应具有高度的立体选择性和区域选择性.

关键词: 螺羟吲哚, 环加成, 甲亚胺叶立德, 晶体结构

A new class of spirooxindole compounds were synthesized by the 1,3-dipolar cycloaddition reaction of 2-arylmethylidene-benzimidazo[2,1-b]thiazol-3-one with azomethine ylide (generated in situ by the reaction of isatin with sarcosine). The structures of the products were characterized thoroughly by IR, MS, NMR techniques, and elemental analysis together with X-ray crystallographic analysis. The results of crystal dif-fraction indicated that this 1,3-dipolar cycloaddition proceeded with well both high stereoselectivity and regioselectivity.

Key words: crystal structure, cycloaddition, azomethine ylide, spirooxindole