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

Authors

  • Tetiana L. Pavlovska State Scientific Institution "Institute for Single Crystals" of national Academy of Sciences of Ukraine
  • Victoria V. Lipson Antidiabetic Drug Laboratory, SI “V.Ya. Danilevsky Institute for Endocrine Pathology Problems”, Academy of Medical Sciences of Ukraine
  • Svetlana V. Shishkina State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine
  • Vladimir I. Musatov State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine
  • Alexander V. Borisov Enamine LTD
  • Alexander V. Mazepa A.V. Bogatsky physico-chemical institute of the National Academy of Sciences of Ukraine

DOI:

https://doi.org/10.1007/5001

Keywords:

arylidenepyruvic acid, azomethine, oxindole, pyrrolizidine, ylide, cycloaddition

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.

Author Biography

Tetiana L. Pavlovska, State Scientific Institution "Institute for Single Crystals" of national Academy of Sciences of Ukraine

аспирант

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Published

2019-07-23

Issue

Vol. 55 No. 7 (2019)

Section

Short Communications