An Efficient Synthesis of 2-Quinoxalinecarboxylic Acid

Abstract

Development of a cost efficient and scaleable process for 2-quinoxalinecarboxylic acid is described. The primarily goals of the development work were to improve the overall yield of the process, to minimize the use of environmentally unacceptable materials, and to obtain a material with a high level of purity. A variety of approaches were examined, and the most efficient method was a condensation of o-phenylenediamine with a monosaccharide followed by a mild peroxide oxidation.

Microscale Parallel Synthesis of Acylated Aminotriazoles Enabling the Development of Factor XIIa and Thrombin Inhibitors

“…To perform the formal removal of the methyl group of 33 h and access compounds exhibiting a quinoxaline scaffold, synthesis shown in Scheme 5 was performed. For this purpose, o ‐phenylenediamine was condensed with D ‐fructose giving substituted quinoxaline 35 , the tetraol side chain of which was then oxidized accessing quinoxaline‐2‐carboxylic acid ( 36 ) [20] . The acid was esterified yielding ester 37 , which was then converted into corresponding aminotriazole 38 using aminoguanidine hydrochloride.…”

Quinoxalin-2-carboxamides: synthesis and pharmacological evaluation as serotonin type-3 (5-HT3) receptor antagonists

“…The 2-(1,2,3,4-tetrahydroxybutyl)quinoxaline (2) and quinoxalin-2-carboxylic acid (3) were synthesized as per method reported 18 . The oxidative cyclization of o-phenylenediamine with d-fructose afforded the former compound with the yield of 46%, which on oxidation with alkaline hydrogen peroxide gave quinoxalin-2-carboxylic acid with the yield of 50%.…”

Synthesis and structure of styryl-substituted azines

“…It was shown recently that quinoline derivatives are promising substrates for the photoinduced electrocyclic reaction [3]. The synthetic potential of these phototransformations is suffi ciently wide and makes it possible to use them for the synthesis of new polyfused heteroaromatic compounds (Scheme 1).π-Conjugated organic compounds based on aromatic systems attract signifi cant attention with respect to the application as semiconductors in organic fi eld transistors (OFETs), organic light-emitting diodes (OLEDs), and photogalvanic batteries, and also as biological active compounds, e.g., potential antitumor agents [4].It is known [5][6][7][8][9][10][11][12] that the main procedure for the synthesis of styrylheterocycles is the aldol-type condensation of methyl derivatives of heterocyclic bases with benzaldehyde derivatives. The primary conditions of the condensation contained the use of relatively strong protic acids and bases, and the range of the possible reaction products was limited.…”

“…It is known [5][6][7][8][9][10][11][12] that the main procedure for the synthesis of styrylheterocycles is the aldol-type condensation of methyl derivatives of heterocyclic bases with benzaldehyde derivatives. The primary conditions of the condensation contained the use of relatively strong protic acids and bases, and the range of the possible reaction products was limited.…”