区域和立体选择性合成新型螺羟吲哚类化合物Regio-andStereo.PDF

2009 年第 29 卷 有 机 化 学 Vol. 29, 2009 第 7 期, 1129～1132 Chinese Journal of Organic Chemistry No. 7, 1129～1132 ·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 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) 摘要 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 Regio- and Stereo-selective Synthesis of Novel Spirooxindole Compounds Li, Xiaofanga,b Yu, Xianyonga Feng, Yaqing*,b 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) Abstract A new class of spirooxindole compounds were synthesized by the 1,3-dipolar cycloaddition re- action 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 diffraction indicated that this 1,3-dipolar cycloaddition proceeded with well both high ste