Quinazolinone is a heterocyclic chemical compound, a quinazoline with a carbonyl group in the C₄N₂ ring. Two

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

s are possible: 2-quinazolinone and 4-quinazolinone, with the 4-isomer being the more common. These compounds are of interest in

medicinal chemistry Medicinal or pharmaceutical chemistry is a scientific discipline at the intersection of chemistry and pharmacy involved with drug design, designing and developing pharmaceutical medication, drugs. Medicinal chemistry involves the identification, ...

. File:2-Quinazolinone.png, 2-Quinazolinone File:4-Quinazolinone.png, 4-Quinazolinone

Synthesis

Common routes to quinazolines involve condensation of

amide In organic chemistry, an amide, also known as an organic amide or a carboxamide, is a chemical compound, compound with the general formula , where R, R', and R″ represent any group, typically organyl functional group, groups or hydrogen at ...

s to anilines with ortho nitrile, carboxylic acids and amides.

Derivatives

Quinazolinone drugs that function as

hypnotic A hypnotic (from Ancient Greek, Greek ''Hypnos'', sleep), also known as a somnifacient or soporific, and commonly known as sleeping pills, are a class of psychoactive drugs whose primary function is to sleep induction, induce sleep and to trea ...

sedative A sedative or tranquilliser is a substance that induces sedation by reducing irritability or Psychomotor agitation, excitement. They are central nervous system (CNS) Depressant, depressants and interact with brain activity, causing its decelera ...

s, methaqualone (Quaalude) for example, usually contain a 4-quinazolinone core with a 2-substituted phenyl group at nitrogen atom 3.

References

{{Chemical classes of psychoactive drugs

Synthesis

Derivatives

See also

References