Synthesis of Dispirocyclopentyl-3,3′-bisoxindoles via Domino Cycloaddition Reactions of 4-Dimethylaminopyridinium Bromides with 3-Phenacylideneoxindoles
Lijuan Lu
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
Search for more papers by this authorCorresponding Author
Chaoguo Yan
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, ChinaSearch for more papers by this authorLijuan Lu
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
Search for more papers by this authorCorresponding Author
Chaoguo Yan
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, China
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou, Jiangsu 225002, ChinaSearch for more papers by this authorAbstract
The base mediated cycloaddition reactions of 4-dimethylamino-1-phenacylpyridinium bromides with two molecular 3-phenacylideneoxindoles in methylene dichloride afforded functionalized dispirocyclopentyl-3,3′-bisoxindoles in good yields and with high diastereoselectivity. The similar cycloaddition reactions of 1-(N,N-dialkylcarbamoylmethyl) and 1-cyanomethyl 4-dimethylamino-pyridinium bromide in refluxing ethanol in the presence of triethylamine also resulted in dispirocyclopentyl-3,3′-bisoxindoles with high diastereoselectivity. The stereochemistry of dispirocyclopentyl-3,3′-bisoxindoles was elucidated on the basis of 1H NMR data and single crystal structures.
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