1769-25-1

Basic information

• Product Name: 2,3-Dimethyl-3H-quinazolin-4-one
• Synonyms: 2,3-Dimethyl-3H-quinazolin-4-one
• CAS NO: 1769-25-1
• Molecular Formula: C₁₀H₁₀N₂O
• Molecular Weight: 174.2
• Mol File: 1769-25-1.mol
• Article Data: 33

Chemical Properties

• Boiling Point: 303 °C at 760 mmHg
• Flash Point: 137 °C
• Appearance: /
• Density: 1.18 g/cm³
• Vapor Pressure: 0.000957mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: 2,3-Dimethyl-3H-quinazolin-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethyl-3H-quinazolin-4-one(1769-25-1)
• EPA Substance Registry System: 2,3-Dimethyl-3H-quinazolin-4-one(1769-25-1)

Safety Data

• Hazardous Substances Data: 1769-25-1(Hazardous Substances Data)

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 58, p. 310, 1993 DOI: 10.1021/jo00054a008Synthesis, p. 180, 1977Tetrahedron Letters, 30, p. 3313, 1989 DOI: 10.1016/S0040-4039(00)99230-X

InChI:InChI=1/C10H10N2O/c1-7-11-9-6-4-3-5-8(9)10(13)12(7)2/h3-6H,1-2H3

Upstream product

• 33809-77-7 2-acetamidobenzamide 
• 74-88-4 methyl iodide 
• 556-61-6 methyl thioisocyanate 
• 89-52-1 o-acetylamino-benzoic acid 
• 87-25-2 2-ethoxycarbonylaniline 
• 121-44-8 triethylamine 
• 4141-08-6 2-Amino-N-methylbenzamid 
• 123-54-6 acetylacetone 
• 75-52-5 nitromethane 
• 615-43-0 2-iodophenylamine 
• 108-24-7 acetic anhydride 
• 78-39-7 Triethyl orthoacetate 
• 525-76-8 2-methyl-4-oxo-3,1-benzoxazine 
• 74-89-5 methylamine 

Downstream Products

• 221198-93-2 2-(2,3-dimethyl-3H-quinazolin-4-ylidene)-1-phenyl-ethanone 
• 1590421-34-3 3-methyl-2-(phenethoxymethyl)quinazolin-4(3H)-one 
• 73283-37-1 2-(2-Oxo-2-phenylethyl)-3-methyl-4(3H)-quinazolinone 
• 56478-61-6 3-methyl-2-styryl-3H-quinazolin-4-one 
• 3137-63-1 4-chloro-2-(trichloromethyl)quinazoline 
• 56478-67-2 2-(4-methoxy-styryl)-3-methyl-3H-quinazolin-4-one 
• 16201-86-8 1,2,3-trimethyl-4-oxo-3,4-dihydroquinazolin-1-ium iodide 
• 35868-44-1 3-methyl-2-styrylquinazolin-4(3H)-one 

Relevant articles and documents

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds

Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is

Palladium-catalyzed four-component carbonylative synthesis of 2,3-disubstituted quinazolin-4(3H)-ones: Convenient methaqualone preparation

A palladium-catalyzed four-component carbonylative cyclization reaction for the synthesis of 2,3-disubstituted quinazolin-4(3H)-ones has been developed. A range of different 2,3-disubstituted quinazolin-4(3H)-one derivatives were prepared in moderate to good yields employing simple and readily accessible 2-iodoanilines, nitro compounds and acid anhydrides as the synthetic precursors. Mo(CO)6 acted both as a solid CO source and a reductant. Notably, methaqualone as a sedative and hypnotic medication can be prepared easily in 68% yield (4b) under our conditions as well.