59564-59-9

Usage

Uses

Used in Pharmaceutical Industry:
3,4-Dihydro-1H-Quinoxalin-2-one is used as a pharmaceutical intermediate for its demonstrated biological activities, such as antifungal and anti-inflammatory properties. Its potential in the development of new drugs makes it a valuable compound in medicinal chemistry for treating various medical conditions.
Used in Agricultural Chemicals Industry:
In the agricultural sector, 3,4-Dihydro-1H-Quinoxalin-2-one is utilized as a component in the formulation of agrochemicals, leveraging its antifungal properties to protect crops from fungal infections and enhance agricultural productivity.
Used in Materials Science:
3,4-Dihydro-1H-Quinoxalin-2-one is employed in materials science for its ability to function as a ligand for metal ions in coordination chemistry. This application is crucial for the development of new materials with specific properties, such as catalysts or sensors, that can be tailored for various industrial uses.
Used in Coordination Chemistry:
3,4-Dihydro-1H-Quinoxalin-2-one is used as a ligand in coordination chemistry to form complexes with metal ions. These complexes have potential applications in catalysis, sensing, and other areas where metal-organic frameworks or coordination compounds are beneficial.

InChI:InChI=1/C8H8N2O/c11-8-5-9-6-3-1-2-4-7(6)10-8/h1-4,9H,5H2,(H,10,11)

Upstream product

• 65182-17-4 5,12-dihydro-5,12-diacetylquinoxalino<2,3-b>quinoxaline 
• 79-11-8 chloroacetic acid 
• 95-54-5 1,2-diamino-benzene 
• 623-73-4 diazoacetic acid ethyl ester 

Downstream Products

• 90917-94-5 4-ethyl-1,2,3,4-tetrahydroquinoxalinone-2 
• 99840-78-5 4-propyl-3,4-dihydro-1H-quinoxalin-2-one 
• 80310-02-7 1-carboxymethyl-1,2,3,4-tetrahydroquinoxaline-3-one 
• 15804-19-0 quinoxaline-2,3-dione 
• 53374-52-0 1-nitroso-3-keto-1,2,3,4-tetrahydroquinoxaline 
• 148858-04-2 4-<(tert-butoxy)carbonyl>-1,2,3,4-tetrahydroquinoxalin-2-one 
• 148858-09-7 ethyl 4,5-dihydroimidazo<1,5-a>quinoxaline-3-carboxylate 
• 120589-86-8 4-acetyl-3,4-dihydroquinoxalin-2(1H)-one 
• 18756-07-5 4-(2-chlorophenyl)-1,2,3,4-tetrahydroquinoxalin-2-one 
• 4937-75-1 4-benzoyl-1,2,3,4-tetrahydroquinoxalin-2-one 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 22298-77-7 3-phenacylidene-3,4-dihydro-1H-quinoxalin-2-one 
• 4937-77-3 4-(phenylsulfonyl)-3,4-dihydroquinoxalin-2(1H)-one 
• 67074-63-9 3,4-dihydro-4-methyl-2(1H)-quinoxalinone 

Relevant academic research and scientific papers

O-H insertion and tandem N-H insertion/cyclization reactions using an iron porphyrin as catalyst with diazo compounds as carbene sources

Iron(III) tetraphenylporphyrin chloride, Fe(TPP)Cl, efficiently catalyzed the insertion of carbenes derived from methyl 2-phenyldiazoacetates into O-H bonds of aliphatic and aromatic alcohols, with yields generally above 80%. Although the analogous N-H insertions are rapid at room temperature, the O-H insertion reactions are slower and required heating in refluxing methylene chloride for about 8 hours using 1.0 mol.% catalyst. Fe(TPP)Cl was also found to be effective for tandem N-H insertion/cyclization reactions when 1,2-diamines and 1,2-alcoholamines were treated with diazo reagents to give piperazinones and morpholinones and related analogs such as quinoxalinones and benzoxazin-2-ones. This approach provides a new one-pot route for synthesizing these classes of heterocyclic compounds.

Electrochemical reduction of quinoxalinoquinoxaline: a revised mechanism

The electrochemical reduction of fluoflavine 2 gives compound 9 to which we had previously assigned a hexahydro-quinoxalinoquinoxaline structure.A crystallographic study of a diacetylated derivative of 9 shows that 9 is in fact 2-(o-aminoanilinomethyl)benzimidazole.This result permits us to propose a detailed reduction mechanism for 2 and its diacetyl derivative 25.

Electrochemical reduction of quinoxalinoquinoxaline

The electrochemical reduction of quinoxalinoquinoxaline gives fluoflavine (2) the structure of which is discussed.The electrochemical reduction of fluoflavine in acidic medium leads to a hexahydroquinolinoquinoxaline.A reduction mechanism is proposed based on cyclic voltammetry results and preparative electrolysis.The results obtained in the case of quinoxalinoquinoxaline are used to rationalize the results obtained in the case of pyrazinopyrazines and pyrazinoquinoxalines.

Studies in 1,2,3,4-Tetrahydro-3-ketoquinoxaline-1-acetic Acid: A Facile Oxidation of Active Methylene Group

The methyl ester (III) of quinoxaline-1-acetic acid (I) has been converted into the corresponding diketo compound (VI) by aerial oxidation in acetone.Decarboxylation and alkaline KMnO4 oxidation of I have also been studied.