Quinazolinone

{{Chembox

| Name=4-Quinazolinone

| ImageFile = 4-Quinazolinone.png

| 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 = {{cascite|correct|CAS}}

| UNII = 84JOT4EY5X

| UNII_Ref = {{fdacite|correct|FDA}}

| 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)

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|Section2={{Chembox Properties

| C=8 | H=6 | N=2 | O=1

| Appearance =

| Density =

| MeltingPt =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

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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.{{Citation |last=Jafari |first=E |display-authors=etal |year=2016 |title=Quinazolinone and quinazoline derivatives: recent structures with potent antimicrobial and cytotoxic activities |journal=Res Pharm Sci |volume=11 |issue=1 |pages=1–14 |pmid=27051427 |pmc=4794932 |postscript=.}}

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.{{cite journal |doi=10.1016/j.tet.2005.07.010|title=Synthesis of quinazolinones and quinazolines|year=2005|last1=Connolly|first1=David J.|last2=Cusack|first2=Declan|last3=O'Sullivan|first3=Timothy P.|last4=Guiry|first4=Patrick J.|journal=Tetrahedron|volume=61|issue=43|pages=10153–10202}}

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

References

{{Reflist}}

{{Chemical classes of psychoactive drugs}}