Expedient Approach for the Synthesis of Trispiropyrrolidine Bisoxindoles Through 1,3-Dipolar Cycloaddition Reactions

Abstract

A series of trispiropyrrolidine bisoxindoles has been achieved via a three-component 1,3-dipolar cycloaddition reaction of 3-aryl-5-arylmethylenespiro[indole-3′,2-[1,3]thiazolane]-2′(1H),4-dione, isatin, and sarcosine in refluxing toluene, which produced the corresponding cycloadducts in good yields (79–88%). Their structures were determined by infrared, ¹H and ¹³C NMR, elementary analysis, and single-crystal x-ray diffraction analysis, and the cycloaddtion reaction was found to be highly regio- and stereoselective.

GRAPHICAL ABSTRACT

Keywords:

• Azomethine ylide
• 1,3-dipolar cycloaddition reactions
• isatin
• trispiropyrrolidine bisoxindoles

SUPPORTING INFORMATION

Full characterization data, ¹H and ¹³C NMR spectra, and x-ray crystallographic materials for this article can be accessed on the publisher’s website.