The study of the three-component interaction between isatin, α-amino acids and N,N’-di(3-carboxypropenoyl)-1,2-ethylenediamine and determination of the structure of the compounds obtained

Authors

  • Ye. I. Syumka National University of Pharmacy, Ukraine
  • L. A. Shemchuk National University of Pharmacy, Ukraine
  • V. P. Chernykh National University of Pharmacy, Ukraine
  • R. G. Redkin National University of Pharmacy, Ukraine

DOI:

https://doi.org/10.24959/ophcj.18.932

Keywords:

bis-spirocyclic systems, 2-oxindole, multi-component reactions, counter synthesis

Abstract

Aim. To develop the preparative methods for obtaining new series of biologically active substances by the three-component interaction between isatin, α-amino acids and N,N’-di(3-carboxypropenoyl)-1,2-ethylenediamine and determine the structure of the compounds obtained.
Results and discussion. Using the three-component cascade transformation of isatin with α-amino acids and N,N’-di(3-carboxypropenoyl)-1,2-ethylenediamine a series of new derivatives of ethylene-N,N’-bis(spiroindole- 3,3’-pyrrolo[3,4-c]pyrrole-2a’,5a’-dihydro-2,2’,6’(1H,1’H,5’H)-trione) was synthesized. It was found that as a result of N,N’-di(3-carboxypropenoyl)-1,2-ethylenediamine cyclization in the course of the reaction the derivatives of N,N’-ethan-1,2-diyl-bis-spiro-2-oxidol[3,2’]-3’H,4’H,5’H-pyrrolo-4’-carboxy-3’-carboxamide were not formed. Instead of the expected hypothetical structures the derivatives of ethylene-N,N’-bis(spiroindole-3,3’-pyrrolo[3,4- c]pyrrole-2a’,5a’-dihydro-2,2’,6’(1H,1’H,5’H)-trione) were selected. The structure of the compounds synthesized was reliably proven by the instrumental methods (1H NMR, IR-spectroscopy), as well as counter synthesis.
Experimental part. The synthesis of compounds was performed using the three-component condensation in the alcoholic-aqueous medium and instrumental methods for determining the structure of organic compounds.
Conclusions. The reaction of the three-component interaction between isatin, α-amino acids and N,N’- di(3-carboxypropenoyl)-1,2-ethylenediamine has been studied. It has been proven that the preparatory method for the three-component cascade transformation of isatin with α-amino acids and ethylenebismaleinimide is an effective method for the synthesis of ethylene-N,N’-bis(spiroindole-3,3’-pyrrolo[3,4-c]pyrrole-2a’,5a’-dihydro-2,2’,6’(1H,1’H,5’H)-triones). The structure of the compounds obtained has been proven.

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Published

2018-03-14

How to Cite

(1)
Syumka, Y. I.; Shemchuk, L. A.; Chernykh, V. P.; Redkin, R. G. The Study of the Three-Component Interaction Between Isatin, α-Amino Acids and N,N’-di(3-Carboxypropenoyl)-1,2-Ethylenediamine and Determination of the Structure of the Compounds Obtained. J. Org. Pharm. Chem. 2018, 16, 34-41.

Issue

Vol. 16 No. 1(61) (2018)

Section

Original Researches

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