4-Quinolone

In this article, we will explore the impact of 4-Quinolone in various areas of daily life. From its influence on technology to its role in society, 4-Quinolone has become a topic of increasing relevance in the contemporary world. Through in-depth analysis, we will examine how 4-Quinolone has shaped the way we interact with the world around us, as well as the implications it has for the future. From its origins to its presence today, this article seeks to shed light on the crucial role 4-Quinolone plays in our daily lives, and how its influence will continue to shape our present and future.

4-Quinolone
Names
Preferred IUPAC name
Quinolin-4(1H)-one
Other names
1H-Quinolin-4-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.336 Edit this at Wikidata
EC Number
  • 210-268-2
UNII
  • InChI=1S/C9H7NO/c11-9-5-6-10-8-4-2-1-3-7(8)9/h1-6H,(H,10,11)
    Key: PMZDQRJGMBOQBF-UHFFFAOYSA-N
  • C1=CC=C2C(=C1)C(=O)C=CN2
Properties
C9H7NO
Molar mass 145.161 g·mol−1
Melting point 208–210 °C (406–410 °F; 481–483 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa).

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]

The tautomeric equilibrium relating 4-quinolone (right) and 4-hydroxyquinoline (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.

The Camps cyclization, a quinoline synthesis giving 2- and 4-hydroxyquinolines.
The Camps cyclization, a quinoline synthesis giving 2- and 4-hydroxyquinolines.

References

  1. ^ Andriole, VT The Quinolones. Academic Press, 1989.
  2. ^ Shi, Pengfei; Wang, Lili; Chen, Kehao; Wang, Jie; Zhu, Jin (2017). "Co(III)-Catalyzed Enaminone-Directed C-H Amidation for Quinolone Synthesis". Organic Letters. 19 (9): 2418–2421. doi:10.1021/acs.orglett.7b00968. PMID 28425721.
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