7265-24-9

Usage

Uses

Used in Pharmaceutical Industry:
2-(2-AMINOPHENYL)-4H-3,1-BENZOXAZIN-4-ONE is used as an intermediate in the synthetic preparation of clavatustides A and B and their enantiomers. Clavatustides are a class of natural products with potential pharmaceutical applications, particularly in the development of new drugs for the treatment of various diseases. The synthesis of these compounds involves the esterification via ring opening of benzoxazinones, which highlights the importance of 2-(2-AMINOPHENYL)-4H-3,1-BENZOXAZIN-4-ONE as a key building block in the development of novel therapeutic agents.

Upstream product

• 612-34-0 N-anthraniloyl-anthranilic acid 
• 21083-34-1 benzoazetinone 
• 37960-65-9 potassium anthranilate 
• 81305-65-9 6-imino-2,4-cyclohexadien-1-ketene 
• 118-48-9 isatoic anhydride 
• 118-92-3 anthranilic acid 
• 134-20-3 2-carbomethoxyaniline 
• 326901-33-1 ethyl 2-(2-nitrobenzoylamino)-benzoate 
• 228581-79-1 ethyl 2-(2-aminobenzoylamino)-benzoate 
• 72367-10-3 2-(2-nitrobenzoylamino)benzoic acid methyl ester 
• 68506-37-6 2-(2-nitrobenzamido)benzoic acid 
• 49854-16-2 methyl 2-(2-aminobenzoylamino)benzoate 
• 610-14-0 2-nitrobenzyl chloride 
• 201230-82-2 carbon monoxide 

Downstream Products

• 96609-69-7 2-[2-(tert-butyloxycarbonyl)aminoethanoyl]aminophenyl-3,1-benzoxazin-4-one 
• 96609-72-2 (S)-2-Amino-N-[2-(4-oxo-4H-benzo[d][1,3]oxazin-2-yl)-phenyl]-propionamide; hydrochloride 
• 96609-71-1 2-[2-aminoethanoyl]aminophenyl-3,1-benzoxazin-4-one hydrochloride 
• 10128-55-9 N-[2-(4-oxo-4H-3,1-benzoxazin-2-yl)phenyl]naphthalene-2-sulfonamide 
• 1581723-72-9 (R)-clavatustide B 
• 1602982-13-7 (R)-clavatustide A 

Relevant academic research and scientific papers

Palladium-catalysed carbonylation of 4-substituted 2-iodoaniline derivatives: carbonylative cyclisation and aminocarbonylation

2-Iodoaniline derivatives were used as bifunctional substrates in palladium-catalysed carbonylation. Depending on the substituents, two types of compounds were synthesised: having methyl or hydrogen in 4-position 2-aryl-benzo[d][1,3]oxazin-4-one derivativ

Unsymmetrically substituted dibenzo[b,f][1,5]-diazocine-6,12(5H,11H)dione—A convenient scaffold for bioactive molecule design

A novel approach for the synthesis of unsymmetrically substituted dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones has been developed. This facile three-step method uses variously substituted 1H-benzo[d][1,3]oxazine-2,4-diones (isatoic anhydrides) and 2-aminobenzoic acids as a starting materials. The obtained products were further transformed into N-alkyl-, N-acetyl- and dithio analogues. Developed procedures allowed the synthesis of unsymmetrical dibenzo[b,f][1,5]diazocine-6,12(5H,11H)diones and three novel heterocyclic scaffolds: benzo[b]naphtho[2,3-f][1,5]diazocine-6,14(5H,13H)dione, pyrido[3,2-c][1,5]benzodiazocine-5,11(6H,12H)-dione and pyrazino[3,2-c][1,5]benzodiazocine-6,12(5H,11H)dione. For 11 of the compounds crystal structures were obtained. The preliminary cytotoxic effect against two cancer (HeLa, U87) and two normal lines (HEK293, EUFA30) as well as antibacterial activity were determined. The obtained dibenzo[b,f][1,5]diazocine(5H,11H)6,12-dione framework could serve as a privileged structure for the drug design and development.

Ring opening of benzoxazinones: An improved and efficient synthesis of clavatustides A & B

Ag2O mediated esterification of (R)-tert-butyl 2-hydroxy-3-phenylpropanoate has been realized via the effective ring opening of benzoxazinones that resulted in the efficient synthesis of cyclodepsipeptides clavatustides A and B and their enanti

NEW FLUORESCENT COMPOUNDS

Disclosed are fluorescent compounds with large Stokes-shift and a process for their preparation. More particularly, disclosed are fluorescent compounds that are colourless. The compounds can be used in compositions for inks, paints and plastics, especiall

1,2-Dihydro-2-thioxo-4H-3,1-benzothiazin-4-one: formation from carbon disulfide and isatoic anhydride

The reaction of isatoic anhydride (1) with carbon disulfide at room temperature unexpectedly afforded 1,2-dihydro-2-thioxo-4H-3,1-benzothiazin-4-one (2). The use of 13C-labeled carbon disulfide elucidated that CS2 was entirely incorp

Facile synthesis of reactive benzoazetinone by flash vacuum pyrolysis of isatoic anhydride

Pyrolysis of isatoic anhydride (3) at 550°C and ca. 1X10-2 torr gave benzoazetinone (1, 80%) as the only product. The existence of 1 was confirmed by low-temperature NMR spectroscopy at -90°C. Above -20°C, 1 was converted to dimer (4, 50%), trimer (5, 22%), and anthranilic acid (6, 12%). Pyrolysis of 3 at 800°C and ca. 1X10-2 torr gave 1-cyanocyclopentadiene (7) in 38% yield.

Role of Intermolecular Reactions in Thermolysis of Aromatic Nitro Compounds in Supercritical Aromatic Solvents

Several nitroarenes were decomposed isothermally in dilute supercritical solution in benzene or toluene and in the vapor phase in the temperature range of 290-380 deg C in sealed glass tubes with pressure up to 100 MPa.The mechanisms of thermolysis are inferred from kinetic studies and product analysis.The initial rate-controlling step for nitrobenzene and p-nitrotoluene decomposition is probably intermolecular hydrogen abstraction to form an ArNO2H radical intermediate.The nature of the transition state is deduced from the activation volume (ΔV*), H/D kinetic-isotope effect, and a linear free-energy relationship between the ionization potential of the hydrogen donor and the logarithm of the decomposition rate.A concurrent pathway for o-nitrotoluene is an intramolecular reaction in which anthranil is an intermediate.The behavior of 1,3-dinitrobenzene and 1,4-dinitrobenzene resembles that of nitrobenzene, whereas 2,4-dinitrotoluene and 2,6-dinitrotoluene decompose in the same manner as o-nitrotoluene.Activation parameters are given and detailed mechanisms proposed.

Fluorescent compounds and their use

Compounds, most of which are novel, and which have been found to have properties very suitable for use in fluorescent inks intended for marking security documents, are of formula I wherein R1, R2, R3 and R4 are independently H, Z or Z-substituted phenyl; and Ar is optionally Z-substituted phenyl or heterocyclyl; in which the Z's are independently selected from C1 4alkyl, OH, C1-C4 alkoxy, halogen, NO2, NH2, C1 4 alkylamino, di(C1 4 alkyl)amino and phenyl; provided that R1, R2, R3 and R4 are not all H when Ar is alkylphenyl or alkoxyphenyl.

Studies in Large Ring Compounds: Part IX - Observations on Cyclodehydration of Anthraniloylanthranilic Acids

Cyclodehydration of anthraniloylanthranilic acids using polyphosphate ester or dicyclohexylcarbodiimide is shown to lead to N-methyldianthranilide (2) and 2-(2-aminophenyl/2-methyl/ethylaminophenbyl)-4H-3,1-benzoxazin-4-ones (6-8).

SYNTHESIS OF QUINAZOLINO-1,4-BENZODIAZEPIN-6,9(5H,7H)-DIONES

2-(2-Nitrophenyl)-3,1-benzoxazin-4-one 3 was elaborated in two ways to afford the title compounds 1 and 2 via novel cyclodehydrations.