Abstract
The thermal cyclization of 2‐alkynylbenzenediazonium salts 2 known as the Richter reaction and leading, as described in the literature, only to 4‐hydroxycinnolines 6 has been studied. A new probable route to these compounds involving intermediate formation of the 4‐chlorocinnolines 4 followed by hydrolysis of the latter to 6 is discussed. A new understanding of the reaction mechanism has induced us to change the reaction conditions in order to synthesize some 4‐bromo‐ (5), 4‐chloro‐ (4), and 4‐hydroxycinnolines 6 as well as 4‐bromo‐(8b) and 4‐chloropyrazolopyridazine 8a.
| Original language | English |
|---|---|
| Pages (from-to) | 775-779 |
| Number of pages | 5 |
| Journal | Liebigs Annalen |
| Volume | 1995 |
| Issue number | 5 |
| DOIs | |
| Publication status | Published - 24 Apr 1995 |
| Externally published | Yes |
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Keywords
- 2‐Diazotolanes
- Cinnolines
- Diazotization
- Pyrazolopyridazines
- Richter reaction
- Tolanes
ASJC Scopus subject areas
- Chemistry(all)
Cite this
Cinnolines and pyrazolopyridazines. — Novel synthetic and mechanistic aspects of the Richter reaction. / Vasilevsky, Sergei F.; Tretyakov, Eugene V.
In: Liebigs Annalen, Vol. 1995, No. 5, 24.04.1995, p. 775-779.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Cinnolines and pyrazolopyridazines. — Novel synthetic and mechanistic aspects of the Richter reaction
AU - Vasilevsky, Sergei F.
AU - Tretyakov, Eugene V.
PY - 1995/4/24
Y1 - 1995/4/24
N2 - The thermal cyclization of 2‐alkynylbenzenediazonium salts 2 known as the Richter reaction and leading, as described in the literature, only to 4‐hydroxycinnolines 6 has been studied. A new probable route to these compounds involving intermediate formation of the 4‐chlorocinnolines 4 followed by hydrolysis of the latter to 6 is discussed. A new understanding of the reaction mechanism has induced us to change the reaction conditions in order to synthesize some 4‐bromo‐ (5), 4‐chloro‐ (4), and 4‐hydroxycinnolines 6 as well as 4‐bromo‐(8b) and 4‐chloropyrazolopyridazine 8a.
AB - The thermal cyclization of 2‐alkynylbenzenediazonium salts 2 known as the Richter reaction and leading, as described in the literature, only to 4‐hydroxycinnolines 6 has been studied. A new probable route to these compounds involving intermediate formation of the 4‐chlorocinnolines 4 followed by hydrolysis of the latter to 6 is discussed. A new understanding of the reaction mechanism has induced us to change the reaction conditions in order to synthesize some 4‐bromo‐ (5), 4‐chloro‐ (4), and 4‐hydroxycinnolines 6 as well as 4‐bromo‐(8b) and 4‐chloropyrazolopyridazine 8a.
KW - 2‐Diazotolanes
KW - Cinnolines
KW - Diazotization
KW - Pyrazolopyridazines
KW - Richter reaction
KW - Tolanes
UR - http://www.scopus.com/inward/record.url?scp=84985863815&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84985863815&partnerID=8YFLogxK
U2 - 10.1002/jlac.1995199505113
DO - 10.1002/jlac.1995199505113
M3 - Article
VL - 1995
SP - 775
EP - 779
JO - Liebigs Annales
JF - Liebigs Annales
SN - 0947-3440
IS - 5
ER -