53463-67-5

Usage

Chemical structure

A benzoxazinone core with a bromophenyl group attached at the 2-position.

Type of compound

Heterocyclic compound.

Elements present

Oxygen and nitrogen atoms.

Potential applications

Pharmaceutical and agrochemical fields.

Value in synthesis

A valuable intermediate for the preparation of various biologically active molecules and materials.

Reactivity and properties

The bromine atom in the phenyl group imparts specific reactivity and properties that can be useful in chemical reactions and applications.

InChI:InChI=1/C14H8BrNO2/c15-10-5-3-4-9(8-10)13-16-12-7-2-1-6-11(12)14(17)18-13/h1-8H

Upstream product

• 106782-83-6 2-(3-bromo-phenyl)-benzo[d][1,3]thiazine-4-thione 
• 1711-09-7 3-bromobenzoyl chloride 
• 118-92-3 anthranilic acid 
• 529-23-7 o-aminobenzaldehyde 
• 2593-28-4 3-bromo-N-hydroxybenzamide 
• 20718-17-6 2-(dimethyl(oxo)-λ⁶-sulfaneylidene)-1-phenylethan-1-one 
• 67836-48-0 2-(3-bromobenzoylamino)benzoic acid methyl ester 

Downstream Products

• 31107-85-4 N-(4-bromo-2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)phenyl)-4-methylbenzenesulfonamide 

Relevant academic research and scientific papers

Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones

A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.

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

Discovery and validation of 2-styryl substituted benzoxazin-4-ones as a novel scaffold for rhomboid protease inhibitors

Rhomboids are intramembrane serine proteases with diverse physiological functions in organisms ranging from archaea to humans. Crystal structure analysis has provided a detailed understanding of the catalytic mechanism, and rhomboids have been implicated in various disease contexts. Unfortunately, the design of specific rhomboid inhibitors has lagged behind, and previously described small molecule inhibitors displayed insufficient potency and/or selectivity. Using a computer-aided approach, we focused on the discovery of novel scaffolds with reduced liabilities and the possibility for broad structural variations. Docking studies with the E. coli rhomboid GlpG indicated that 2-styryl substituted benzoxazinones might comprise novel rhomboid inhibitors. Protease in vitro assays confirmed activity of 2-styryl substituted benzoxazinones against GlpG but not against the soluble serine protease α-chymotrypsin. Furthermore, mass spectrometry analysis demonstrated covalent modification of the catalytic residue Ser201, corroborating the predicted mechanism of inhibition and the formation of an acyl enzyme intermediate. In conclusion, 2-styryl substituted benzoxazinones are a novel rhomboid inhibitor scaffold with ample opportunity for optimization.

TBHP/CoCl2-mediated intramolecular oxidative cyclization of N-(2-formylphenyl)amides: An approach to the construction of 4H-3,1-benzoxazin-4-ones

The intramolecular oxidative cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as an oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives and features readily available starting materials and mild reaction conditions. The intramolecular cyclization of N-(2-formylphenyl)amides has been realized through an oxidative C(sp2)-O(sp2) bond-forming reaction between an aldehyde carbon and amide oxygen. This new strategy, which uses tert-butyl hydroperoxide (TBHP) as the oxidant and CoCl2 as the catalyst, allows for the efficient Co-catalyzed synthesis of useful benzoxazin-4-one derivatives.

Synthesis and characterization of quinazoline derivatives: Search for hybrid molecule as diuretic and antihypertensive agents

To explore the pharmacological and structure-activity relationship of a series of N-substituted-(4-oxo-2-substituted-phenylquinazolin-3-(4H)-yl), substituted benzene sulfonamide derivatives (1-25) were synthesized from substituted anthranilic acids derive

Synthesis of 2-Aryl-4H-3,1-Benzoxazin-4-ones: A Class of α-Chymotrypsin Inhibitors

Twenty one derivatives of 2-aryl-4H-3,1-benzoxazin-4-one were synthesized and their potential therapeutically significance and structureactivity relationship were tested against α-chymotrypsin. Majority of synthesized compounds showed significant in vitro α-chymotrypsin inhibitory properties having IC50values in the range of 5.42 ± 1.66 - 41.27 ± 1.33 μM, whereas standard inhibitor chymostatin have IC50 value 7.13 ± 1.06 μM. In the present series compounds 2-(2-fluorophenyl)-4H-3,1-benzoxazin-4-one (3h), 2-(2-bromophenyl)-4H-3,1- benzoxazin-4-one (3n) and 2-(1-naphthyl)-4H-3, 1-benzoxazin-4-one (3t) with IC50values 7.22 ± 0.75, 6.99 ± 0.29 and 5.42 ± 1.66 μM, respectively were found to be most active members of series, even better than standard inhibitor a-chymostatin.

HETEROCYCLIC COMPOUNDS REGULATING CLOTTING

Compounds of formula (I) as factor VII-tissue factor inhibitors as well as novel benzoxazin derivatives are disclosed, wherein R1, R2, R3, X and Y are as defined in the specification. These compounds, and pharmaceutically acceptable salts thereof, have be

Selectively herbicidal 2-substituted-4H-3,1-benzoxazin-4-ones

Unwanted vegetation is combated in the presence of grain crops and soybeans by post-emergent application of one or more of the following compounds: 2-(m-chlorophenyl)-4H-3,1-benzoxazin-4-one, 2-(m-trifluoromethylphenyl)-4H-3,1-benzoxazin-4-one, 2-(2-thienyl)-4H-3,1-benzoxazin-4-one, 2-(o-trifluoromethylphenyl)-4H-3,1-benzoxazin-4-one, 2-(p-trifluoromethylphenyl)-4H-3,1-benzoxazin-4-one, 2-(4-methyl-1,2,3-thiadizole-5-yl)-benzoxazin-4-one 2-(m-bromophenyl)-4H-3,1-benzoxazin-4-one.