This is an old revision of this page, as edited by 117.205.56.240 (talk) at 07:46, 23 September 2011. The present address (URL) is a permanent link to this revision, which may differ significantly from the current revision.
Revision as of 07:46, 23 September 2011 by 117.205.56.240 (talk)(diff) ← Previous revision | Latest revision (diff) | Newer revision → (diff)
| |
| Names | |
|---|---|
| IUPAC name Cinnoline | |
| Other names BenzEMBL = 479792 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).
 Y verify (what is ?)
Infobox references
|
|Section2={{Chembox Properties | Formula=C8H6N2 | MolarMass=130.15 g/mol | Appearance= | Density=
Cinnolines are cinnoline derivatives. A classic organic reaction for synthesizing cinnolines is the Widman-Stoermer synthesis, a ring-closing reaction of an α-vinyl- aniline with hydrochloric acid and sodium nitrite:
The sodium nitrite is first converted to nitrous acid which then forms the electrophilic intermediate dinitrogen trioxide. The next intermediate is the stable Nitrosamine with goes on to lose water forming the diazonium salt which then reacts with the vinyl group in the ring-closing step. A conceptually related reaction is the Bamberger triazine synthesis towards triazines.
Another cinnoline method is the Borsche cinnoline synthesis.
Safety
Cinnoline is toxic.
See also
References
- Name Reactions and Reagents in Organic Synthesis Bradford P. Mundy, Michael G. Ellerd, Frank G. Jr. Favaloro 2005 ISBN 0471228540