SYNTHESIS OF DISPIRO[1-BENZOTHIOPHENE-2,3'-PYRROLIDINE- 2',3''-INDOLINE]-2'',3-DIONES IN CYCLOADDITION REACTION

Authors

  • Ying Zhou Department of Medicine and Nursing, Shijiazhuang Vocational College of Finance and Economics, Shijiazhuang Xuefu Road, Hebei 050061,China;
  • Yulin Huang 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
  • Guihua Tang 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
  • Xiaofang Li 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

DOI:

https://doi.org/10.1007/5119

Keywords:

azomethine ylide, 1-benzothiophen-3(2H)-one, isatin, sarcosine, 1, 3-dipolar cycloaddition.

Abstract

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.

Author Biographies

Ying Zhou, Department of Medicine and Nursing, Shijiazhuang Vocational College of Finance and Economics, Shijiazhuang Xuefu Road, Hebei 050061,China;

Department of medicine and nursing

Yulin Huang, 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

School of Chemistry and Chemical Engineering

Guihua Tang, 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

School of Chemistry and Chemical Engineering

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Published

2019-11-12

Issue

Vol. 55 No. 11 (2019)

Section

Original Papers