20492-07-3

Basic information

• Product Name: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE
• Synonyms: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE;2-(furan-2-yl)-4H-3,1-benzoxazin-4-one
• CAS NO: 20492-07-3
• Molecular Formula: C₁₂H₇NO₃
• Molecular Weight: 213.18888
• Mol File: 20492-07-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 326°C at 760 mmHg
• Flash Point: 151°C
• Appearance: /
• Density: 1.37g/cm³
• Vapor Pressure: 0.000221mmHg at 25°C
• Refractive Index: 1.653
• CAS DataBase Reference: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE(20492-07-3)
• EPA Substance Registry System: 2-(2-FURYL)-3,1-BENZOXAZIN-4(4H)-ONE(20492-07-3)

Safety Data

• Hazardous Substances Data: 20492-07-3(Hazardous Substances Data)

Usage

Naturally occurring compound

DIMBOA is a compound that occurs naturally in certain plants, particularly in the grass family.

Plant defense against pests and diseases

DIMBOA plays a role in plant defense against pests and diseases, due to its strong anti-microbial and anti-feedant properties.

Agricultural applications

DIMBOA has been studied for its potential use in agriculture, as it has shown promise in controlling pests and improving crop yields.

Pharmaceutical potential

DIMBOA has been investigated for its potential use in pharmaceuticals, due to its anti-inflammatory and antioxidant properties.

Versatile compound

DIMBOA is a versatile compound with potential applications in both agriculture and medicine.

InChI:InChI=1/C12H7NO3/c14-12-8-4-1-2-5-9(8)13-11(16-12)10-6-3-7-15-10/h1-7H

Upstream product

• 527-69-5 2-furancarbonyl chloride 
• 118-92-3 anthranilic acid 
• 1431098-07-5 C₁₂H₈INO₃ 
• 529-23-7 o-aminobenzaldehyde 
• 50-00-0 formaldehyd 
• 19771-81-4 furan-2-carboxylic acid 2-bromoanilide 
• 615-36-1 2-bromoaniline 
• 551-93-9 2-aminoacetophenone 
• 1875-58-7 N-(2-acetylphenyl)furan-2-carboxamide 
• 201230-82-2 carbon monoxide 
• 144223-33-6 2-furoyl-1H-1,2,3-benzotriazole 
• 615-43-0 2-iodophenylamine 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 1373758-56-5 3-(furan-2-yl)-5H-1,4,2-dioxazol-5-one 

Downstream Products

• 104830-71-9 2-(2-furyl)-3,4-dihydro-5H-1,3,4-benzotriazepin-5-one 
• 84141-26-4 N-[2-(hydrazinylcarbonyl)phenyl]furan-2-carboxamide 
• 329067-78-9 N-(2-(p-tolyl-carbamoyl)phenyl)furan-2-carboxamide 
• 1310340-98-7 2-(furan-2-yl)-3-(phenylamino)quinazolin-4(3H)-one 
• 1310340-99-8 N-{2-[(4-sulfamoylphenyl)carbamoyl]phenyl}furan-2-carboxamide 
• 942031-13-2 3-(4-chlorobenzylideneamino)-2-(furan-2-yl)quinazolin-4(3H)-one 
• 1310341-06-0 3-(2-chlorobenzylideneamino)-2-(furan-2-yl)quinazolin-4(3H)-one 
• 942031-16-5 3-(benzylideneamino)-2-(furan-2-yl)quinazolin-4(3H)-one 
• 663216-59-9 3-(4-hydroxy-3-methoxybenzylideneamino)-2-(furan-2-yl)quinazolin-4(3H)-one 
• 1310341-07-1 3-(4-hydroxybenzylideneamino)-2-(furan-2-yl)quinazolin-4(3H)-one 
• 1310341-08-2 3-(4-methylbenzylideneamino)-2-(furan-2-yl)quinazolin-4(3H)-one 
• 1310341-09-3 3-(3-bromobenzylideneamino)-2-(furan-2-yl)quinazolin-4(3H)-one 
• 1310341-10-6 3-(4-cyanobenzylideneamino)-2-(furan-2-yl)quinazolin-4(3H)-one 
• 1310341-11-7 3-(2,5-dimethoxybenzylideneamino)-2-(furan-2-yl)quinazolin-4(3H)-one 

Relevant articles and documents

Pd-Catalyzed Carbonylative Synthesis of 4H-Benzo[d][1,3]Oxazin-4-Ones Using Benzene-1,3,5-Triyl Triformate as the CO Source

A facile synthesis of 4H-benzo[d][1,3]oxazin-4-one derivatives by Pd-catalyzed carbonylative cross-coupling between N-(ortho-bromoaryl)amides and benzene-1,3,5-triyl triformate (TFBen) was developed. This procedure does not require the toxic and flammable gas CO as the carbonyl source and tolerates a wide scope of functional groups. Remarkably, 4H-benzo[d][1,3]oxazin-4-ones incorporated to natural products and drugs can be constructed by this method.

C2-substituted quinazolinone derivatives exhibit A1 and/or A2A adenosine receptor affinities in the low micromolar range

Antagonists of the adenosine receptors (A1 and A2A subtypes) are widely researched as potential drug candidates for their role in Parkinson's disease-related cognitive deficits (A1 subtype), motor dysfunction (A2A subtype) and to exhibit neuroprotective properties (A2A subtype). Previously the benzo-α-pyrone based derivative, 3-phenyl-1H-2-benzopyran-1-one, was found to display both A1 and A2A adenosine receptor affinity in the low micromolar range. Prompted by this, the α-pyrone core was structurally modified to explore related benzoxazinone and quinazolinone homologues previously unknown as adenosine receptor antagonists. Overall, the C2-substituted quinazolinone analogues displayed superior A1 and A2A adenosine receptor affinity over their C2-substituted benzoxazinone homologues. The benzoxazinones were devoid of A2A adenosine receptor binding, with only two compounds displaying A1 adenosine receptor affinity. In turn, the quinazolinones displayed varying degrees of affinity (low micromolar range) towards the A1 and A2A adenosine receptor subtypes. The highest A1 adenosine receptor affinity and selectivity were favoured by methyl para-substitution of phenyl ring B (A1Ki = 2.50 μM). On the other hand, 3,4-dimethoxy substitution of phenyl ring B afforded the best A2A adenosine receptor binding (A2AKi = 2.81 μM) among the quinazolinones investigated. In conclusion, the quinazolinones are ideal lead compounds for further structural optimization to gain improved adenosine receptor affinity, which may find therapeutic relevance in Parkinson's disease-associated cognitive deficits and motor dysfunctions as well as exerting neuroprotective properties.

Palladium-Catalyzed Olefination of 4H-Benzo[d][1,3]oxazin-4-one Derivatives with Activated Alkenes via Preferential Cyclic Imine-N-Directed Aryl C-H Activation

A palladium-catalyzed chelation-assisted selective ortho C-H bond olefination of biologically active 4H-benzo[d][1,3] oxazin-4-one derivatives with activated olefins has been achieved. The products are obtained in good yields with high regio- and stereose