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 language | English |
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Pages (from-to) | 1725-1733 |
Number of pages | 9 |
Journal | Russian Chemical Bulletin |
Volume | 57 |
Issue number | 8 |
DOIs | |
Publication status | Published - 1 Aug 2008 |
Externally published | Yes |
Keywords
- Anilines
- Cinnolines
- Diacetylenes
- Diazonium salts
- Diazotization
- Furo[3,2-c]cinnolines
- Spectrophotometry
- The Richter cyclization
ASJC Scopus subject areas
- Chemistry(all)