A novel heterocyclization of 1-acetylenyl-9,10-anthraquinones

M. S. Shvartsberg, I. D. Ivanchikova, S. F. Vasilevsky

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Abstract

1-Acetylenyl-9,10-anthraquinones react with an excess of NH 2 NH 2 at 80-115°C to give a mixture of substituted 7H-dibenzo[de,h]quinolin-7-ones and anthra[9, 1-cd]-1,2-diazepin-8-ones. The latter compounds undergo reductive contraction of the seven-membered ring to give the corresponding 7H-dibenzo[de,h]quinolin-7-ones. Bulky substituents in position 2 of the initial acetylenylanthraquinones prevent the formation of the seven-membered heterocycle. A scheme of the cyclocondensation was proposed.

Original languageEnglish
Pages (from-to)1971-1974
Number of pages4
JournalRussian Chemical Bulletin
Volume47
Issue number10
DOIs
Publication statusPublished - 1 Jan 1998
Externally publishedYes

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Keywords

  • 1-acetylenyl-9,10-anthraquinones
  • 4H-anthra[9,1-cd]-1,2-diazepin-8-ones
  • 7H-dibenzo[de,h]quinolin-7-ones
  • Contraction of the seven-membered heterocycle
  • Cyclocondensation
  • Hydrazine

ASJC Scopus subject areas

  • Chemistry(all)

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