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 |
|---|---|
| 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 |
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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)
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 journal › Article
}
TY - JOUR
T1 - Studies on cyclization of o-(alka-1,3-diynyl)arenediazonium salts
AU - Vinogradova, O. V.
AU - Sorokoumov, V. N.
AU - Vasilevskii, S. F.
AU - Balova, I. A.
PY - 2008/8/1
Y1 - 2008/8/1
N2 - 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.
AB - 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.
KW - Anilines
KW - Cinnolines
KW - Diacetylenes
KW - Diazonium salts
KW - Diazotization
KW - Furo[3,2-c]cinnolines
KW - Spectrophotometry
KW - The Richter cyclization
UR - http://www.scopus.com/inward/record.url?scp=68949160952&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=68949160952&partnerID=8YFLogxK
U2 - 10.1007/s11172-008-0228-z
DO - 10.1007/s11172-008-0228-z
M3 - Article
VL - 57
SP - 1725
EP - 1733
JO - Russian Chemical Bulletin
JF - Russian Chemical Bulletin
SN - 1066-5285
IS - 8
ER -