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

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

Research output: Contribution to journalArticle

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

Fingerprint

Cyclization
Aniline Compounds
Salts
Spectrophotometry
Methanol
Hydrolysis
Derivatives
Chemical analysis
cinnoline

Keywords

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Studies on cyclization of o-(alka-1,3-diynyl)arenediazonium salts. / Vinogradova, O. V.; Sorokoumov, V. N.; Vasilevskii, S. F.; Balova, I. A.

In: Russian Chemical Bulletin, Vol. 57, No. 8, 01.08.2008, p. 1725-1733.

Research output: Contribution to journalArticle

Vinogradova, O. V. ; Sorokoumov, V. N. ; Vasilevskii, S. F. ; Balova, I. A. / Studies on cyclization of o-(alka-1,3-diynyl)arenediazonium salts. In: Russian Chemical Bulletin. 2008 ; Vol. 57, No. 8. pp. 1725-1733.
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