A Facile Regioselective 1, 3-Dipolar Cycloaddition Reaction for the Synthesis of Dispiro[Indole-3, 2-Pyrrolidine-3′, 5″-[1, 3]Thiazolidine] Derivatives. (April 2015)

• Record Type: Journal Article
• Authors: Feng, Guo-Liang; Li, Yue; Geng, Li-Jun
• Is Part Of: Journal of chemical research. Volume 39:Number 3(2015)
• Page Start: 134
• Page End: 137
• Publication Date: 2015-04
• Subjects: 1, 3-dipolar cycloaddition reactions -- dispiro[indole-3, 2′-pyr rolidine-3′, 5″-[1, 3]thiazolidine] -- azomethine ylides -- isatin; Chemistry -- Research -- Periodicals; Chemistry -- Periodicals; 540.5
• DOI: 10.3184/174751915X14231323398218
• Languages: English
• ISSNs: 1747-5198

Abstract

The 1, 3-dipolar cycloaddition reaction of azomethine ylides generated in situ from isatin and sarcosine with 5-arylmethylene-3-phenyl-2-thioxothiazolidin-4-one in refluxing toluene produced the 2″-thioxodispiro[indole-3, 2′-pyrrolidine-3′, 5″-[1, 3]thiazolidine]-2, 4″-dione derivatives in good yields (80–88%). The structures were assigned by 1 H NMR, IR, elementary analysis and single crystal X-ray diffraction analysis through which the cycloaddition reaction was found to be highly regio- and stereo-selective.