Quinolinone

Quinolinone is a class of organic compounds that are formally derived from quinoline by replacement of a hydrogen atom with a keto group. Quinolinones are a subclass of quinolines and are often used as building blocks in the synthesis of more complex compounds, including many pharmaceuticals.

Structure and Properties

Quinolinones are characterized by a bicyclic structure, consisting of a benzene ring fused to a pyridine ring. The keto group is located on the pyridine ring, replacing a hydrogen atom. This gives quinolinones their characteristic reactivity and properties.

Quinolinones are typically yellow or light brown solids, although their exact physical properties can vary depending on the specific compound. They are generally soluble in organic solvents and exhibit strong fluorescence, which can be useful in certain applications.

Synthesis

There are several methods for the synthesis of quinolinones, including the Skraup synthesis, the Doebner-Miller reaction, and the Combes quinoline synthesis. These methods all involve the reaction of an aniline or a related compound with a suitable carbonyl compound.

Applications

Quinolinones are used as building blocks in the synthesis of a wide range of compounds. They are particularly important in the pharmaceutical industry, where they are used to produce a variety of drugs, including antibiotics, antidepressants, and antimalarial drugs.

For example, the quinolinone derivative levofloxacin is a widely used antibiotic, while the antimalarial drug mefloquine is also based on a quinolinone structure.

See Also

• Quinoline
• Isoquinoline
• Pyridine
• Benzene