Synthesis of complex dispirocyclopentanebisoxindoles via cycloaddition reactions of 4-dimethylamino-1-alkoxycarbonylmethylpyridinium bromides with 2-oxoindolin-3-ylidene derivatives |
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| Affiliation: | 1. Institute of Chemistry, Chernyshevsky Saratov State University, Saratov, Russia;2. Institute of Biochemistry and Physiology of Plants and Microorganisms, Russian Academy of Sciences, Saratov, Russia |
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| Abstract: | The cycloaddition reactions of 4-dimethylamino-1-alkoxycarbonylmethylpyridinium bromides with various 2-oxoindolin-3-ylidene derivatives in ethanol in the presence of triethylamine afforded the unprecedented dispirocyclopentanebisoxindole derivatives in good yields and in high diastereoselectivity. Under similar reaction conditions, the reactions of 1-alkoxycarbonylmethylpyridinium bromides with 3-phenacylideneoxindoles only resulted in 4-oxo-3-(2-oxoindolin-3-ylidene)-4-arylbutanoates. The stereochemistry of the complex spirooxindoles was established by 1H NMR data and single crystal structures. |
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| Keywords: | 1,3-Dipolar cycloaddition Dimethylaminopyridine Spirooxindole |
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