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Chemistry of Heterocyclic Compounds

, Volume 41, Issue 2, pp 208–215 | Cite as

Pyrrolocoumarins. 1. Synthesis and Spectroscopic Investigation of 7-Oxo- and 1,2,7-Trioxo-1,2-dihydropyrano-[3,2-e]indole and Their Derivatives

  • T. E. Khoshtariya
  • L. N. Kurkovskaya
  • L. T. Bochoidze
  • K. T. Batsikadze
  • N. T. Mirziashvili
  • I. G. Abesadze
  • M. I. Sikharulidze
  • V. G. Turabelidze
  • V. O. Ananiashvili
  • T. O. Dzhashi
  • M. G. Maisuradze
Article

Abstract

A preparative route is proposed for the synthesis of the novel heterocyclic systems 7-oxo- and 1,2,7-trioxo-1,2-dihydropyrano[3,2-e]indole using classical Fischer and Sandmeyer methods respectively. We have studied various conditions for cyclization of the starting coumarin 6-isonitrosoacetamide and the methyl or ethyl pyruvate 6-coumarinylhydrazones. The syn- and anti-form ratio of the latter and the structure of all of the synthesized compounds were determined using spectroscopic data analysis.

Keywords

6-(isonitrosoacetamido)coumarin 7-oxo-1,2-dihydropyrano[3,2-e]indole Sandmeyer reaction Fischer reaction syn-Z- and anti-E-forms of pyruvate ester 6-coumarinylhydrazones 1,2,7-trioxo-1,2-dihydropyrano[3,2-e]indole cyclization 

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Copyright information

© Springer Science+Business Media, Inc. 2005

Authors and Affiliations

  • T. E. Khoshtariya
    • 1
  • L. N. Kurkovskaya
    • 1
  • L. T. Bochoidze
    • 1
  • K. T. Batsikadze
    • 1
  • N. T. Mirziashvili
    • 1
  • I. G. Abesadze
    • 1
  • M. I. Sikharulidze
    • 1
  • V. G. Turabelidze
    • 1
  • V. O. Ananiashvili
    • 1
  • T. O. Dzhashi
    • 1
  • M. G. Maisuradze
    • 1
  1. 1.Department for the Technology of Organic SubstancesGeorgian Technical UniversityTbilisiGeorgia

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