Studies on cyclization of o-(alka-1,3-diynyl)arenediazonium salts

O. V. Vinogradova, V. N. Sorokoumov, S. F. Vasilevskii, I. A. Balova

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7 Citations (Scopus)

Abstract

The Richter reaction of o-(alka-1,3-diynyl)arenediazonium salts, obtained by diazotization of diacetylenic derivatives of anilines, leads to 3-alkynyl-4-chloro- or 3-alkynyl-4-bromocinnolines and/or 3-alkynyl-4- hydroxycinnolines (the latter cyclize into furo[3,2-c]-cinnolines under the reaction conditions). 3-Alkynyl-4-chlorocinnolines undergo solvolysis in methanol giving rise to 3-alkynyl-4-methoxycinnolines, the subsequent hydrolysis of which also gives furo[3,2-c]cinnolines. Effects of the nature of substituents in the aromatic ring and of the reaction conditions on the product composition and yields have been established. The reaction course has been studied by spectrophotometry.

Original languageEnglish
Pages (from-to)1725-1733
Number of pages9
JournalRussian Chemical Bulletin
Volume57
Issue number8
DOIs
Publication statusPublished - 1 Aug 2008
Externally publishedYes

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Keywords

  • Anilines
  • Cinnolines
  • Diacetylenes
  • Diazonium salts
  • Diazotization
  • Furo[3,2-c]cinnolines
  • Spectrophotometry
  • The Richter cyclization

ASJC Scopus subject areas

  • Chemistry(all)

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