Quinazolinone

4-Quinazolinone

Names
Preferred IUPAC name Quinazolin-4(3H)-one
Other names 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
Identifiers
CAS Number	491-36-1  Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL266540
ChemSpider	56797
PubChem CID	63112
UNII	84JOT4EY5X  Y
InChI InChI=1S/C8H6N2O/c11-8-6-3-1-2-4-7(6)9-5-10-8/h1-5H,(H,9,10,11)
SMILES O=C2\N=C/Nc1ccccc12
Properties
Chemical formula	C8H6N2O
Molar mass	146.149 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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. ^[1]

• 
  2-Quinazolinone
• 
  4-Quinazolinone

Synthesis

Common routes to quinazolines involve condensation of amides to anilines with ortho nitrile, carboxylic acids and amides. ^[2]

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.

See also

• Idelalisib (Zydelig)
• Cloroqualone
• SL-164 (Dicloqualone)
• Diproqualone
• Etaqualone
• Mebroqualone
• Mecloqualone
• Methylmethaqualone
• Nitromethaqualone

References

1. Jafari, E; et al. (2016), "Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities", Res Pharm Sci, 11 (1): 1–14, PMC   4794932 , PMID   27051427.
2. Connolly, David J.; Cusack, Declan; O'Sullivan, Timothy P.; Guiry, Patrick J. (2005). "Synthesis of quinazolinones and quinazolines". Tetrahedron. 61 (43): 10153–10202. doi:10.1016/j.tet.2005.07.010.