Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (07): 1129-1132. Previous Articles     Next Articles

Reports

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 出版日期:2009-07-22 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 Online:2009-07-22 Published:2009-07-22
  • Contact: Feng, Yaqing

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