Peculiarities of the Reaction of 2-Amino-1,4-naphthoquinones with 2,2-Dihydroxy-1H-indene-1,3(2H)-dione

L. M. Gornostaev, O. I. Fominykh, T. I. Lavrikova, Yu G. Khalyavina, Yu V. Gatilov, G. A. Stashina

Research output: Contribution to journalArticlepeer-review

Abstract

The reaction of 2-amino-1,4-naphthoquinones with ninhydrin at 50–60°C in acetic acid leads to 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones. The products were isolated as hydrates, and, when heated in DMSO with methanesulfonic acid or in acetic acid in the presence of sulfuric acid, they converted into 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones. The rate of the conversion of 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones to 13-R-benzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones in solutions of sulfuric acid in acetic acid is linearly related to the Hammett acidity function.

Original languageEnglish
Pages (from-to)1716-1725
Number of pages10
JournalRussian Journal of Organic Chemistry
Volume55
Issue number11
DOIs
Publication statusPublished - 1 Nov 2019

Keywords

  • 13-R-benzo[f]isohromeno[4,3-b]indole-5,7,12(13H)-triones
  • 2,2-dihydroxy-1H-indene-1,3-(2H)-dione
  • 2-alkylamino-1,4-naphthoquinones
  • 4b,11b-dihydroxy-4b,5-dihydrobenzo[f]indeno[1,2-b]indole-6,11,12(11bH)-triones
  • acid catalysis
  • domino reactions
  • 5-HYDROXY-1,4-NAPHTHOQUINONE
  • DERIVATIVES

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