SYNTHESIS OF 5-ARYLMETHYLIDENE-3-(ARYLMETHYLIDENEAMINO)THIAZOLIDINE-2,4-DIONES <i>VIA</i> TRIAZINE RING CLEAVAGE OF TETRAHYDROIMIDAZOTHIAZOLOTRIAZINEDIONES AND THEIR REACTIONS WITH AZOMETHINE YLIDES

Authors

  • Alexei N. Izmest'ev N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia National University of Science and Technology (MISiS), 4 Leninsky Ave., Moscow 119049, Russia
  • Galina A. Gazieva N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Natalya G. Kolotyrkina N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Elena D. Daeva N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia
  • Angelina N. Kravchenko N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia Plekhanov Russian University of Economics, 36 Stremyanny Lane, Moscow 117997, Russia

DOI:

https://doi.org/10.1007/5896

Keywords:

aldehydes, spiro compounds, spirooxindoles, thiazolidine-2, 4-diones, cleavage, cycloaddition.

Abstract

Cleavage of 1,3-dimethyl-3,3a,9,9a-tetrahydroimidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-2,7(1H,6H)-diones upon treatment with aromatic aldehydes has been shown to afford (Z)-5-arylmethylidene-3-((E)-arylmethylideneamino)thiazolidine-2,4-diones bearing two identical or
different arylmethylidene fragments at the exocyclic nitrogen atom and at position 5 of thiazolidine cycle. 1,3-Dipolar cycloaddition reaction of thiazolidine-2,4-dione derivatives with azomethine ylide generated from isatin and sarcosine gave diastereomerically pure dispiro[indole-3,2'-pyrrolidine-3',5''-thiazolidine]-2,2'',4''-triones in good yields. Dispiro compound with two 4-methoxyphenyl fragments exhibited slight antiproliferative activity toward CCRF-CEM (leukemia) and CAKI-1 (renal cancer) cell lines.

Author Biography

Alexei N. Izmest'ev, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Ave., Moscow 119991, Russia National University of Science and Technology (MISiS), 4 Leninsky Ave., Moscow 119049, Russia

Russian Academy of sciences

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Published

2020-12-18

Issue

Vol. 56 No. 12 (2020)

Section

Original Papers