Quinolines
Quinolines
Quinolines (pronounced: kwin-uh-lines) are a class of organic compounds with the formula C9H7N. They are aromatic heterocyclic compounds, with a benzene ring fused to a pyridine ring.
Etymology
The term "quinoline" comes from the Latin word "quinus," meaning "five each," referring to the two rings of five atoms each in its structure.
Structure and Properties
Quinolines are characterized by a double-ring structure, one of which is a benzene ring (a six-membered ring with three double bonds), and the other is a pyridine ring (a six-membered ring with two double bonds and a nitrogen atom). This structure gives quinolines their unique chemical properties, including their aromaticity and their ability to participate in electrophilic substitution reactions.
Synthesis
Quinolines can be synthesized through several methods, including the Skraup synthesis, the Doebner-Miller reaction, and the Combes quinoline synthesis. These methods all involve the reaction of aniline with an aldehyde or ketone in the presence of an acid catalyst.
Uses
Quinolines have a wide range of uses in medicine and other fields. They are used as the basis for many pharmaceutical drugs, including chloroquine and quinine, which are used to treat malaria. They are also used in the synthesis of dyes, in the rubber industry, and as a corrosion inhibitor in steel.
Related Terms
- Benzene: A simple aromatic ring compound. It is a colorless and highly flammable liquid with a sweet smell.
- Pyridine: A basic heterocyclic organic compound. It is structurally related to benzene, with one methine group (=CH−) replaced by a nitrogen atom.
- Chloroquine: A medication used to prevent and to treat malaria. It is also used to treat amebiasis.
- Quinine: A medication used to treat malaria and babesiosis. It can also be used for leg cramps.
External links
- Medical encyclopedia article on Quinolines
- Wikipedia's article - Quinolines
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