5779-27-1

Upstream product

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 95-85-2 2-hydroxy-5-chloro-aniline 
• 611-73-4 Benzoylformic acid 
• 17200-29-2 5-chloro-benzoxazole 

Downstream Products

• 1335225-52-9 (+)-(S)-6-chloro-3-phenyl-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-one 

Relevant academic research and scientific papers

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).

Preparation method of 3-aryl-2H-benzo [beta] [1, 4] benzoxazine-2-ketone compound

The invention discloses a preparation method of a 3-aryl-2H-benzo [beta] [1, 4] benzoxazine-2-ketone compound, which comprises the following steps: carrying out magnetic stirring on a reaction substrate 2-aminophenol compound and a ketonic acid compound i

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.

[Ir(P-OP)]-catalyzed asymmetric hydrogenation of diversely substituted C=N-containing heterocycles

Iridium(I) complexes of enantiomerically pure phosphine-phosphite ligands ([Ir(Cl)(cod)(P - OP)]) efficiently catalyze the enantioselective hydrogenation of diverse C=N-containing heterocyclic compounds (benzoxazines, benzoxazinones, benzothiazinones, and quinoxalinones; 25 examples, up to 99% ee). A substrate-to-catalyst ratio as high as 2000:1 was reached.