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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (05): 735-739. 上一篇    下一篇

研究简报

1,3-偶极环加成反应合成螺噻唑并[3,2-a]嘧啶类化合物

李筱芳*,1,2，于贤勇1，冯亚青2   

  1. (1湖南科技大学化学化工学院 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)
    (2天津大学化工学院应用化学系 天津 300072)
  • 收稿日期:2009-08-19 修回日期:2009-10-30 发布日期:2009-12-14
  • 通讯作者: 冯亚青 E-mail:yqfeng@tju.edu.cn
  • 基金资助:

    国家级.国家自然科学基金

Synthesis of Spiro Thiazolo[3,2-a]pyrimidine Compounds by 1,3-Dipolar Cycloaddition Reaction

Li Xiaofang*,1, 2 Yu Xianyong1 Feng Yaqing2   

  1. (1 Key Laboratory of Theoretical Chemistry and Molecular Simulation of Ministry of Education, Hunan Province College Key Laboratory of QSAR/QSPR, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201)
    (2 School of Chemical Engineering and Technology, Tianjin University, Tianjin 300072)
  • Received:2009-08-19 Revised:2009-10-30 Published:2009-12-14
  • Contact: Feng Yaqing E-mail:yqfeng@tju.edu.cn

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通过2-芳亚甲基-6,7-二氢-5H-噻唑并[3,2-a]嘧啶-3-酮(1a～1j)与甲亚胺叶立德(经靛红与肌氨酸反应原位生成)进行的l,3-偶极环加成反应, 合成了10个新的螺噻唑并[3,2-a]嘧啶类化合物2a～2j. 采用NMR、质谱、IR、元素分析以及X射线单晶衍射等多种谱学技术对产物2a～2j进行了结构表征, 研究结果表明此类反应具有高度的立体选择性和区域选择性.

关键词: 噻唑并[3,2-a]嘧啶, 甲亚胺叶立德, l,3-偶极环加成, 立体和区域选择性

A new class of spiro thiazolo[3,2-a]pyrimidine compounds 2a～2j were synthesized by the 1,3-dipolar cycloaddition reaction of 2-arylmethylidene-6,7-dihydro-5H-thiazolo[3,2-a]pyrimidin-3-one (1a～1j) with azomethine ylide (generated in situ by the reaction of isatin with sarcosine). The structures of the products 2a～2j were determined and characterized thoroughly by NMR, MS, IR techniques, elemental analysis, and X-ray crystallographic analysis. The results of experiment indicated that this 1,3-dipolar cycloaddition proceeded with high stereoselectivity and regioselectivity.

Key words: thiazolo[3,2-a]pyrimidine, azomethine ylide, 1,3-dipolar cycloaddition, stereoselectivity and regioselectivity