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词条 4-Quinolone
释义

  1. Synthesis

  2. References

{{Use dmy dates|date=August 2012}}{{Chembox
| ImageFile = 4-Quinolone.svg
| ImageSize = 180px
| ImageAlt =
| IUPACName =
| OtherNames = 1H-Quinolin-4-one
|Section1={{Chembox Identifiers
| CASNo = 529-37-3
| PubChem = 69141
| EC_number = 210-268-2
| UNII = M1O131WXFO
| InChI=1S/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11)
| InChIKey = PMZDQRJGMBOQBF-UHFFFAOYSA-N
| SMILES = C1=CC=C2C(=C1)C(=O)C=CN2 }}
|Section2={{Chembox Properties
| C=9|H=7|N=1|O=1
| MolarMass =
| Appearance =
| Density =
| MeltingPtC = 208-210
| BoilingPt =
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}4-Quinolone is an organic compound derived from quinoline. It and 2-quinolone are the two most important parent (meaning simplified) quinolones. 4-Quinolone exists in equilibrium with a minor tautomer, 4-hydroxyquinoline (CAS#611-36-9). Aside from pedagogical interest, 4-Quinolone is of little intrinsic value but its derivatives, the 4-quinolone antibiotics represent a large class of important drugs.[1]{{clear-left}}

Synthesis

The chemical synthesis of quinolones often involves ring-closing reactions.[2] Such reactions often install a hydroxyl group (an –OH functional group) on the carbon across from the ring nitrogen (i.e., the C-4 positions). An example of such a synthesis is the Camps cyclization, which, depending on starting materials and reaction conditions, can give both 2-hydroxyquinolines (B) and 4-hydroxyquinolines (A) as shown. The hydroxyquinolines tautomerize to the quinolones.

References

1. ^Andriole, VT The Quinolones. Academic Press, 1989.
2. ^{{cite journal|title=Co(III)-Catalyzed Enaminone-Directed C-H Amidation for Quinolone Synthesis|author=Shi, Pengfei|author2=Wang, Lili|author3=Chen, Kehao|author4=Wang, Jie|author5=Zhu, Jin|journal= Organic Letters|year=2017|volume=19|pages=2418–2421|pmid=28425721| doi=10.1021/acs.orglett.7b00968}}

1 : 4-Quinolones

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