6640-47-7

Usage

Synthesis Reference(s)

Chemical and Pharmaceutical Bulletin, 5, p. 45, 1957The Journal of Organic Chemistry, 37, p. 4136, 1972 DOI: 10.1021/jo00798a038

InChI:InChI=1/C8H8N4/c9-7-8(10)12-6-4-2-1-3-5(6)11-7/h1-4H,(H2,9,11)(H2,10,12)

Upstream product

• 67-56-1 methanol 
• 2213-63-0 2,3-dichloroquinoxaline 
• 64-17-5 ethanol 
• 460-19-5 ethanedinitrile 
• 95-54-5 1,2-diamino-benzene 
• 91-19-0 2,3-diethynylquinoxaline 
• 471-46-5 Oxalamide 
• 1196-57-2 quinoxalin-2⁽¹⁾-one 
• 15804-19-0 quinoxaline-2,3-dione 

Downstream Products

• 69637-93-0 6,13-dihydro-5,6,7,12,13,14-hexaazapentacene 
• 531-46-4 5,12-dihydroquinoxalino[2,3-b]quinoxaline 
• 38956-57-9 2-trans-styryl-1H-imidazo[4,5-b]quinoxaline 
• 18217-53-3 2,3-diphenyl-pyrazino[2,3-b]quinoxaline 
• 35015-91-9 3-amino-2(1H)-quinoxalinone 
• 6640-51-3 2-(1H-imidazo[4,5-b]quinoxalin-2-yl)-phenol 
• 80102-43-8 2-phenylpyrazino<2,3-b>quinoxaline 

Relevant academic research and scientific papers

Exploration of quinoxaline derivatives as antimicrobial and anticancer agents

Novel 2 and 3-substituted quinoxaline derivatives were synthesized through various synthetic pathways, among which cyanoacetamide and cyanoacetohydrazide quinoxaline derivatives 4a-c and 11a-c, respectively, were synthesized. Furthermore, methoxy quinoxaline derivatives 3c and quinoxaline derivatives bearing substituted pyridines 6a,b, 12a,b, and 13a,b were designed to be synthesized. However, we have synthesized acrylohydrazide 5a,b and 7/acrylamide derivatives, Schiff base analogues 14a-f, pyrazole derivatives 15a-e, amide derivatives 16a-f, guanidine derivatives 16 g,h as well as, quinoxalin-2-methylallyl propionate derivative 14g. All the synthesized compounds were confirmed via spectral data and elemental analyses. Moreover, the newly synthesized compounds were evaluated for their antimicrobial activity (Gm +ve, Gm ?ve in comparison to Gentamycin a standard) and fungi (in comparison to Ketoconazole as a standard). Thus, compound 16b showed promising antimicrobial activity against B. subtilis, P. vulgaris, and S. mutants with values ranging from 20 to 27-mm zone of inhibition. While compounds 5a, 14e,f, and 16a,c,d,g,h showed potent antimicrobial activity. Moreover, the National Cancer Institute (NCI) selected 20 compounds that were submitted for anticancer screening against 60 types of cancer cell lines. The most active compounds are 5b and 12a where compound 5b containing 2,4-dichlorophenyl moiety at cyanoacetamide linkage of hydrazine quinoxaline backbone exerted significant growth inhibition activity against Leukemia MOLT-4, Renal cancer UO-31, and Breast cancer MCF-7. In addition, compound 12a having 4,6-diaminopyridinone side chain at position-3 of quinoxaline nucleus exhibited remarkable anticancer activity against renal cancer UO-31.

Synthesis of substituted dipyrido[3,2-a:2′,3′-c]phenazines and a new heterocyclic dipyrido[3,2-f:2′,3′-h]quinoxalino[2,3-b]quinoxaline

Three new α,α′-diimine ligands were synthesized based on condensation of 1,10-phenanthroline-5,6-dione with 1,2-phenylenediamine derivatives using different approaches. All compounds were fully characterized by IR, 1H and 13C NMR, UV-visible, and MS spectroscopies. We report the first example of a dipyrido[3,2-f:2′,3′-h]quinoxalino[2,3-b]quinoxaline, which exhibits a strong absorption at 430 nm and an interesting electrochemical behavior. These new molecules may have biological potential and are of synthetic and technological importance.

Permanganate Oxidation of Quinoxaline and Its Derivatives

The oxidation reaction of a series of quinoxaline derivatives, using KMnO4 in the presence or absence of NaOH, are described.Neutral oxidation of 2-chloro- and 2,3-dichlorodioxalines 2-4 afforded the corresponding chloro- and dichloropyrazinedicarboxilic acids 13 and 14 in good yield.On the other hand, oxidation of quinoxalin-2(1H)-one and 1,4-dihydroquinoxaline-2,3-dione derivatives in alkaline medium gave different products, with the quinoxalin-2(1H)-one (5) forming 1,4-dihydroquinoxaline-2,3-dione (9), while various substituted quinoxalin-2,3-dione derivatives (see 9-11) gave a new type of dimeric products.The structural assignments for the new compounds were based on spectroscopic data.

On the Amination of Azaheterocycles. A New Procedure for the Introduction of an Amino Group

A new method of amination of diazines and triazines, using potassium amide, liquid ammonia and potassium permanganate, has been described.

Imidazoquinoxaline fungicides

Compounds of the formula STR1 wherein R1 is hydrogen, alkali metal, alkyl, substituted alkyl, alkylsulfenyl or acyl; R2 is alkyl or cyclopropyl; R3 is hydrogen, chlorine, bromine or fluorine; n and p are 0 or 1 and A is a mineral acid are useful as fungicides. A representative compound is 6-chloro-2-ethyl-1H-imidazo[4,5-b]quinoxaline.