| Revision as of 16:08, 7 August 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'UNII', 'ChEBI').← Previous edit |
Latest revision as of 06:36, 24 July 2023 edit undoSekio (talk | contribs)75 edits Preparation is detailed in the section below, and uses modern IUPAC terminology. |
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{{short description|Chemical compound}} |
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{{chembox |
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{{chembox |
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| Watchedfields = changed |
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| verifiedrevid = 414071879 |
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| verifiedrevid = 443525481 |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile=Cinnoline numbering.png |
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| ImageFile=Cinnoline numbering.png |
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|ImageSize=180px |
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| ImageSize=160px |
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|IUPACName=Cinnoline |
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| ImageFileL1 = Cinnoline-3D-balls.png |
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| ImageAltL1 = Cinnoline molecule |
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|OtherNames=Benzopyridazine |
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| ImageNameL1 = C=black, H=white, N=blue |
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| ImageFileR1 = Cinnoline-3D-spacefill.png |
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| ImageNameR1 = C=black, H=white, N=blue |
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| ImageAltR1 = Cinnoline molecule |
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| PIN = Cinnoline<ref>{{cite book |author=] |date=2014 |title=Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 |publisher=] |pages=212 |doi=10.1039/9781849733069 |isbn=978-0-85404-182-4}}</ref> |
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| OtherNames = Benzopyridazine |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8853 |
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| ChemSpiderID = 8853 |
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| InChI = 1/C8H6N2/c1-2-4-8-7(3-1)5-6-9-10-8/h1-6H |
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| InChI = 1/C8H6N2/c1-2-4-8-7(3-1)5-6-9-10-8/h1-6H |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = WCZVZNOTHYJIEI-UHFFFAOYSA-N |
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| StdInChIKey = WCZVZNOTHYJIEI-UHFFFAOYSA-N |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo=253-66-7 |
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| CASNo=253-66-7 |
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| PubChem=9208 |
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| PubChem=9208 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = N5KD6I506O |
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| UNII = N5KD6I506O |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 36617 |
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| ChEBI = 36617 |
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| SMILES = n1nccc2ccccc12 |
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| SMILES = n1nccc2ccccc12 |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=8 | H=6 | N=2 |
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| Formula=C<sub>8</sub>H<sub>6</sub>N<sub>2</sub> |
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| Appearance= |
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| MolarMass=130.15 g/mol |
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| Appearance= |
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| Density= |
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| MeltingPtC=39 |
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| Density= |
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| BoilingPt= |
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| MeltingPtC=39 |
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| pKa=2.64<ref>Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., ''Determination of Organic Structures by Physical Methods'', Academic Press, New York, 1955.</ref> |
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| BoilingPt= |
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| Solubility= |
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| pKa=2.64<ref>Brown, H.C., et al., in Baude, E.A. and Nachod, F.C., ''Determination of Organic Structures by Physical Methods'', Academic Press, New York, 1955.</ref> |
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| Solubility= |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| MainHazards= |
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| FlashPt= |
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| AutoignitionPt = |
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'''Cinnoline''' is an ] ] with the formula C<sub>8</sub>H<sub>6</sub>N<sub>2</sub>. It is ]ic with ], ] and ]. |
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'''Cinnoline''' is an ] ] with the formula C<sub>8</sub>H<sub>6</sub>N<sub>2</sub>. It is ]ic with other ]s including ], ] and ]. |
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==Properties== |
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==Properties== |
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The free base can be obtained as an oil by treatment of the ] with base. It co-crystallizes with one molecule of ether as white silky needles, (m.p. 24-25 °C) upon cooling ethereal solutions. The free ] melts at 39 °C. It has a taste resembling that of ] and leaves a sharp irritation for some time. Cinnoline derivatives are obtained from oxycinnolin carboxylic acid, which is formed by digesting orthophenyl propiolic acid diazo chloride with water. Oxycinnolin carboxylic acid on heating gives oxycinnoline, melting at 225 °C, which with ] gives chlorcinnolin. This substance is reduced by ]s and ] to dihydrocinnolin. |
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The free base can be obtained as an oil by treatment of the ] with base. It co-crystallizes with one molecule of ether as white silky needles, (m.p. 24–25 °C) upon cooling ethereal solutions. The free ] melts at 39 °C. It has a taste resembling that of ] and leaves a sharp irritation for some time. |
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==Discovery and synthesis== |
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==Discovery and synthesis== |
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The compound was first obtained in impure form by cyclization of the ] ''o''-C<sub>6</sub>H<sub>4</sub>(NH<sub>2</sub>)C≡CCO<sub>2</sub>H in water to give 4-hydroxycinnoline-3-carboxylic acid. This material could be decarboxylated and the hydroxyl group reductively removed to give the parent heterocycle. This reaction is called the '''Richter cinnoline synthesis'''<ref>] "Über Cinnolinderivate" Chemische Berichte, 1883, volume 16, pp 677-683.</ref> Improved methods exist for its synthesis. It can be prepared by ] of ] with freshly precipitated ]. It can be isolated as the ].<ref>Parrick, J.; Shaw, C. J. G. and Mehta, L. K., "Pyridazines, cinnolines, benzocinnolines and phthalazines", Rodd's Chemistry of Carbon Compounds (2nd Edition), 2000, 4, 1-69.</ref> |
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The compound was first obtained in impure form by cyclization of the ] ''o''-C<sub>6</sub>H<sub>4</sub>(NH<sub>2</sub>)C≡CCO<sub>2</sub>H in water to give 4-hydroxycinnoline-3-carboxylic acid. This material could be ] and the hydroxyl group reductively removed to give the parent heterocycle. This reaction is called the '''Richter cinnoline synthesis'''.<ref>{{cite journal | author = Victor von Richter | title = Über Cinnolinderivate | journal = Chemische Berichte | year = 1883 | volume = 16 | pages = 677–683 | doi=10.1002/cber.188301601154| author-link = Victor von Richter | url = https://zenodo.org/record/1425289 }}</ref> Improved methods exist for its synthesis. It can be prepared by ] of ] with freshly precipitated ]. It can be isolated as the ].<ref>{{cite book |author1=Parrick, J. |author2=Shaw, C. J. G. |author3=Mehta, L. K. | chapter = Pyridazines, cinnolines, benzocinnolines and phthalazines | title = Rodd's Chemistry of Carbon Compounds | edition = 2nd | year = 2000 | volume = 4 | pages = 1–69}}</ref> |
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'''Cinnolines''' are cinnoline derivatives. A classic ] for synthesizing cinnolines is the '''Widman-Stoermer synthesis'''<ref>''Name Reactions and Reagents in Organic Synthesis'' Bradford P. Mundy, Michael G. Ellerd, Frank G. Jr. Favaloro '''2005''' ISBN 0471228540</ref>, a ] of an α-vinyl- ] with ] and ]: |
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'''Cinnolines''' are cinnoline derivatives. A classic ] for synthesizing cinnolines is the '''Widman–Stoermer synthesis''',<ref>{{cite book | title = Name Reactions and Reagents in Organic Synthesis |author1=Bradford P. Mundy |author2=Michael G. Ellerd |author3=Frank G. Jr. Favaloro | year = 2005 | isbn = 0-471-22854-0}}</ref> a ] of an α-vinyl- ] with ] and ]: |
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The sodium nitrite is first converted to ] which then forms the ] intermediate ]. The next intermediate is the stable ] with goes on to lose water forming the ] which then reacts with the vinyl group in the ring-closing step. A conceptually related reaction is the ] towards triazines. |
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The sodium nitrite is first converted to ] which then forms the ] intermediate ]. The next intermediate is the stable ] with goes on to lose water forming the ] which then reacts with the vinyl group in the ring-closing step. A conceptually related reaction is the ] towards triazines. |
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Another cinnoline method is the ]. |
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Another cinnoline method is the ]. |
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==See also== |
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==See also== |
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* cinnoline]] |
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* ] |
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==References== |
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==References== |
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