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Synthesis of dispiro[1-benzothiophene-2,3'-pyrrolidine-2',3”-indoline]-2”,3-diones in cycloaddition reaction

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Chemistry of Heterocyclic Compounds Aims and scope

The 1,3-dipolar cycloaddition of azomethine ylides derived from isatin and sarcosine to (Z)-2-(arylmethylidene)-1-benzothiophen-3(2H)- ones afforded novel dispiro[1-benzothiophene-2,3'-pyrrolidine-2',3”-indoline]-2”,3-diones in moderate yields. The structures of all the products were characterized by NMR, IR, HRMS together with X-ray crystallographic analysis. The reaction gives two diastereomeric products. This result is different from the cycloaddition of isatin, sarcosine, and other exocyclic olefins which generally afford only one product.

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Figure 1.
Scheme 1.
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Scheme 2.

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Authors and Affiliations

  1. Department of Medicine and Nursing, Shijiazhuang Vocational College of Finance and Economics, Shijiazhuang Xuefu Road, Hebei, 050061, China

    Ying Zhou

  2. Key Laboratory of Theoretical Organic Chemistry and Functional Molecules, Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan Taoyuan Road, Hunan, 411201, China

    Yulin Huang, Guihua Tang & Xiaofang Li

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  1. Ying Zhou
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  2. Yulin Huang
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  3. Guihua Tang
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  4. Xiaofang Li
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Correspondence to Xiaofang Li.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(11), 1044–1049

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Zhou, Y., Huang, Y., Tang, G. et al. Synthesis of dispiro[1-benzothiophene-2,3'-pyrrolidine-2',3”-indoline]-2”,3-diones in cycloaddition reaction. Chem Heterocycl Comp 55, 1044–1049 (2019). https://doi.org/10.1007/s10593-019-02575-6

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