Quinazolinone

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title: "Quinazolinone" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["quinazolinones"] topic_path: "general/quinazolinones" source: "https://en.wikipedia.org/wiki/Quinazolinone" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Name=4-Quinazolinone | ImageFile = 4-Quinazolinone.png | ImageClass = skin-invert-image | ImageSize = 120px | PIN = Quinazolin-4(3H)-one | OtherNames = 4(3H)-Quinazolinone; 4(1H)-Quinazolinone; 3,4-Dihydroquinazolin-4-one; 4(3H)-Quinazolone; 4-Hydroxyquinazoline; 4-Oxo-3,4-dihydroquinazoline; 4-Oxoquinazoline; 4-Quinazolinol; 4-Quinazolinone; 4-Quinazolone |Section1={{Chembox Identifiers | CASNo = 491-36-1 | CASNo_Ref = | UNII = 84JOT4EY5X | UNII_Ref = | PubChem = 63112 | ChemSpiderID = 56797 | ChEMBL = 266540 | SMILES = O=C2\N=C/Nc1ccccc12 | InChI = InChI=1S/C8H6N2O/c11-8-6-3-1-2-4-7(6)9-5-10-8/h1-5H,(H,9,10,11) |Section2={{Chembox Properties | C=8 | H=6 | N=2 | O=1 | Appearance = | Density = | MeltingPt = | BoilingPt = | Solubility = |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt =

Quinazolinone is a heterocyclic chemical compound, a quinazoline with a carbonyl group in the C4N2 ring. Two isomers are possible: 2-quinazolinone and 4-quinazolinone, with the 4-isomer being the more common. These compounds are of interest in medicinal chemistry. File:2-Quinazolinone.png|2-Quinazolinone File:4-Quinazolinone.png|4-Quinazolinone

Synthesis

Common routes to quinazolines involve condensation of amides to anilines with ortho nitrile, carboxylic acids and amides.

Derivatives

Quinazolinone drugs that function as hypnotic/sedatives, methaqualone (Quaalude) for example, usually contain a 4-quinazolinone core with a 2-substituted phenyl group at nitrogen atom 3.

References

References

  1. Jafari, E. (2016). "Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities". Res Pharm Sci.
  2. (2005). "Synthesis of quinazolinones and quinazolines". Tetrahedron.

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quinazolinones