917085-52-0

Upstream product

• 95-55-6 2-amino-phenol 
• 99-73-0 para-bromophenacyl bromide 
• 7099-87-8 4-bromophenylglyoxylic acid 
• 273-53-0 benzoxazole 
• 20201-26-7 ethyl 4-bromophenylglyoxylate 
• 61821-71-4 3-(4-bromophenyl)-2H-benzo[b][1,4]oxazine 
• 61821-70-3 2-(2-acetylamino-phenoxy)-1-(4-bromo-phenyl)-ethanone 
• 61821-84-9 3,3'-bis-(4-bromo-phenyl)-2H,2'H-[2,2']bi[benzo[1,4]oxazinyl] 

Downstream Products

• 1255772-40-7 3-(4-bromophenyl)-3,4-dihydro-2H-1,4-benzoxazin-2-one 

Relevant academic research and scientific papers

Metal-free sp3 C-H bond oxidation and functionalization of α-bromoketones to quinoxalinone, benzoxazinone, and benzothiazinone heterocyclic compounds

A series of heterocyclic compounds (benzothiazinones, benzoxazinones and quinoxalinones) were efficiently synthesized in excellent yields via α-bromoketones with o-substituted aniline (2-aminothiophenol, aryl-1,2-diamines and 2-aminophenol). This protocol accomplishes sp3 C-H bond oxidation and functionalization in one-pot without any metal catalyst.

α-Keto Acids as Triggers and Partners for the Synthesis of Quinazolinones, Quinoxalinones, Benzooxazinones, and Benzothiazoles in Water

A general and efficient method for the synthesis of quinazolinones, quinoxalinones, benzooxazinones, and benzothiazoles from the reactions of α-keto acids with 2-aminobenzamides, benzene-1,2-diamines, 2-aminophenols, and 2-aminobenzenethiols, respectively, is described. The reactions were conducted under catalyst-free conditions, using water as the sole solvent with no additive required, and successfully applied to the synthesis of sildenafil. More importantly, these reactions can be conducted on a mass scale, and the products can be easily purified through filtration and washing with ethanol (or crystallized).

Niobium-promoted reaction of α-phenylglyoxylic acid with ortho-functionalized anilines: Synthesis of 2-arylbenzothiazoles and 3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones

A new and general method to prepare 2-arylbenzothiazoles and 3-aryl-2H-benzo[b][1,4]benzoxazin-2-ones by the reaction of α-arylglyoxylic acid with o-aminothiophenol and o-aminophenol respectively is described. The use of ammonium niobium oxalate (ANO) as the catalyst and PEG-400 as the solvent were crucial to afford the title compounds in good yields and selectivity. The reaction time can be reduced from hours to few minutes when ultrasound is used as an alternative energy source.

Unexpected TFA-catalyzed tandem reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids: Synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones and cephalandole A

A convenient and efficient method for the TFA-catalyzed synthesis of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones via a tandem reaction of benzo[d]oxazoles with 2-oxo-2-arylacetic acids was reported for the first time. The efficiency of this transformation was demonstrated by compatibility with a wide range of functional groups. The synthetic utility of this method was confirmed by the synthesis of the natural product cephalandole A. Moreover, a plausible mechanism for the formation of 3-aryl-2H-benzo[b][1,4]oxazin-2-ones involving ring-opening and cyclization steps is proposed. The present synthetic route to 3-aryl-2H-benzo[b][1,4]oxazin-2-ones could be readily scaled up to gram quantity without difficulty.

Oxone-mediated oxidative carbon-heteroatom bond cleavage: Synthesis of benzoxazinones from benzoxazoles with α-oxocarboxylic acids

A metal-free oxidative cleavage of benzoxazoles using Oxone as an oxidant has been developed. The in situ formed o-aminophenol has been proved to react successfully with α-oxocarboxylic acids affording the benzoxazinones in moderate to good yields. The Royal Society of Chemistry.

An efficient synthetic protocol for quinoxalinones, Benzoxazinones, and benzothiazinones from 2-oxo-2-aryl-acetyl bromide precursors

α-Bromoketones undergo selenium dioxide oxidation to yield reactive 2-oxo-2-arylacetyl bromides that are trapped by aryl-1,2-diamines, 1,2-aminophenol or 1,2-aminothiophenol to give quinoxalinones, benzoxazinones, and benzothiazinones, respectively, in go

The first general, highly enantioselective lewis base organocatalyzed hydrosilylation of benzoxazinones and quinoxalinones

The first general, highly enantioselective hydrosilylation of benzoxazinones and quinoxalinones has been developed. The chiral Lewis base organocatalysis that are readily accessible from (1S,2R)-ephedrine and (1R,2S)-ephedrine promoted the title reaction to afford various chiral dihydrobenzoxazinones and dihydroquinoxalinones with good yields as well as good enantioselectivities.