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    杨雅琴, 葛松兰, 马磊. 盐酸硫胺(VB1)催化合成四氢咔唑类化合物[J]. 华东理工大学学报(自然科学版), 2016, (4): 499-507. DOI: 10.14135/j.cnki.1006-3080.2016.04.010
    引用本文: 杨雅琴, 葛松兰, 马磊. 盐酸硫胺(VB1)催化合成四氢咔唑类化合物[J]. 华东理工大学学报(自然科学版), 2016, (4): 499-507. DOI: 10.14135/j.cnki.1006-3080.2016.04.010
    YANG Ya-qin, GE Song-lan, MA Lei. Synthesis of Tetrahydrocarbazole Derivatives Using Thiamine Hydrochloride (VB1) as Efficient Catalyst[J]. Journal of East China University of Science and Technology, 2016, (4): 499-507. DOI: 10.14135/j.cnki.1006-3080.2016.04.010
    Citation: YANG Ya-qin, GE Song-lan, MA Lei. Synthesis of Tetrahydrocarbazole Derivatives Using Thiamine Hydrochloride (VB1) as Efficient Catalyst[J]. Journal of East China University of Science and Technology, 2016, (4): 499-507. DOI: 10.14135/j.cnki.1006-3080.2016.04.010

    盐酸硫胺(VB1)催化合成四氢咔唑类化合物

    Synthesis of Tetrahydrocarbazole Derivatives Using Thiamine Hydrochloride (VB1) as Efficient Catalyst

    • 摘要: 1,2,3,4-四氢咔唑类衍生物广泛应用于医药领域。在盐酸硫胺(VB1)催化作用下,苯肼盐酸盐和环己酮在乙醇中反应,可以简便、高产率地得到四氢咔唑类化合物。将不同基团取代的环己酮和含有吸电子或供电子基团的苯肼用VB1进行底物扩展,大部分目标产物的产率在90%以上,证实在合成四氢咔唑的反应中,VB1是一种温和、高效、环保型的催化剂。对VB1进行回收再利用,催化效率没有明显降低。

       

      Abstract: The tetrahydrocarbazole derivatives are widely used in pharmaceutical chemistry.A simple and highly efficient method was developed for the construction of tetrahydrocarbazole derivatives from phenylhydrazine hydrochloride and cyclohexanone in the presence of thiamine hydrochloride (VB1) in ethanol.This protocol relies on the use of various cyclohexanone and phenylhydrazine hydrochloride with electron-donating and electron-withdrawing groups to access tetrahydrocarbazole scaffolds with a wide scope.Most of the target products catalyzed by VB1 were obtained in good to excellent yields (>90%).VB1 acted as an efficient,mild and non-toxic catalyst in the reaction,and it could be reused without reducing the catalytic efficiency.

       

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