112259-29-7

Upstream product

• 91-19-0 2,3-diethynylquinoxaline 

Downstream Products

• 149633-95-4 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5R,6S)-6-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-5,6,7,8-tetrahydro-quinoxalin-5-yl ester 
• 149633-95-4 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (5R,6S)-6-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-5,6,7,8-tetrahydro-quinoxalin-5-yl ester 

Relevant academic research and scientific papers

Metabolism of Bicyclic Aza-arenes by Pseudomonas putida to Yield Vicinal cis-Dihydrodiols and Phenols

Metabolism of the aza-arenes quinoline, isoquinoline, quinazoline, and quinoxaline by a mutant strain of the bacterium Pseudomonas putida resulted in attack at the carbocyclic ring (to yield stable cis-dihydrodiols and phenols) and at the heterocyclic ring (to yield phenols and ring cleavage products).

Structure and Stereochemistry of cis-Dihydro Diol and Phenol Metabolites of Bicyclic Azaarenes from Pseudomonas putida UV4

Biotransformation of quinoline, isoquinoline, quinoxaline and quinazoline using growing cultures of Pseudomonas putida UV4 yielded cis-dihydro diols from the oxidation of the carbocyclic aromatic ring.Aromatic hydroxylation was observed in both carbocyclic and heterocyclic rings.Ring cleavage of the quinoline skeleton to yield anthranilic acid, and cis-diol formation (with alkene bond reduction) to yield cis-5,6,7,8-tetrahydroquinazoline-5,6-diol from quinazoline were observed.The cis-dihydro diol metabolites of quinoline (5,6- and 7,8-) and quinoxaline (5,6-) were found to be optically pure, while metabolism of isoquinoline gave on e homochiral (5,6-) and one racemic 7,8-) cis-dihydro diol product.The absolute configuration of the cis-dihydro diol metabolites have been determined using 1H NMR analyses, stereochemical correlations and X-ray crystallography methods.