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

Ying Zhou, Yulin Huang, Guihua Tang, Xiaofang Li
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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.

Keywords


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

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