1,3-Dipolar cycloaddition of (E)-4-(4-chlorophenyl)-2-oxobut-3-enic acid to 2-oxindole azomethine ylides
| Autor: | Tetiana L. Pavlovska, Alexander V. Mazepa, A. V. Borisov, Victoria V. Lipson, Svetlana V. Shishkina, Vladimir I. Musatov |
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| Rok vydání: | 2019 |
| Předmět: |
chemistry.chemical_classification
010405 organic chemistry Carboxylic acid Isatin Organic Chemistry 010402 general chemistry 01 natural sciences Medicinal chemistry Cycloaddition 0104 chemical sciences NMR spectra database chemistry.chemical_compound chemistry Ylide 1 3-Dipolar cycloaddition Oxindole Conformational isomerism |
| Zdroj: | Chemistry of Heterocyclic Compounds. 55:679-683 |
| ISSN: | 1573-8353 0009-3122 |
| Popis: | The α-keto carboxylic acid motif has been embedded to the novel spirooxindolepyrrolizidines via a three-component 1,3-dipolar cycloaddition of 2-oxindole azomethine ylides generated in situ from isatin and proline with (E)-4-(4-chlorophenyl)-2-oxo-but-3-enoic acid as dipolarophile. The stereochemistry of cycloaddition was confirmed by NMR spectra data as well as with the calculations of the geometrical structures of all possible conformers and charge distribution in the reacting systems by means of M06-2X /cc-pVTZ basis set in the Gaussian 09 program. |
| Databáze: | OpenAIRE |
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