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1,3-DIPOLAR CYCLOADDITION OF (E)-4-(4-CHLOROPHENYL)-2-OXOBUT-3-ENIC ACID TO 2-OXINDOLE AZOMETHINE YLIDES

Tetiana L. Pavlovska, Victoria V. Lipson, Svetlana V. Shishkina, Vladimir I. Musatov, Alexander V. Borisov, Alexander V. Mazepa
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Abstract


The a-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.


Keywords


arylidenepyruvic acid; azomethine; oxindole; pyrrolizidine; ylide; cycloaddition

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