129227-28-7

Upstream product

• 31595-63-8 3-hydrazineylidene-3,4-dihydroquinoxalin-2(1H)-one 
• 98-88-4 benzoyl chloride 
• 129227-24-3 3-(2-benzylidenehydrazinyl)quinoxalin-2(1H)-one 
• 95-54-5 1,2-diamino-benzene 
• 65-85-0 benzoic acid 
• 51347-93-4 2‐chloro‐3‐hydrazinylquinoxaline 
• 100-52-7 benzaldehyde 
• 2213-63-0 2,3-dichloroquinoxaline 
• 15804-19-0 quinoxaline-2,3-dione 
• 160591-43-5 benzoic acid N'-(3-oxo-3,4-dihydro-quinoxalin-2-yl)-hydrazide 
• 97111-40-5 2-chloro-3-(2'-benzylidenehydrazino)quinoxaline 
• 91895-65-7 4-chloro-1-phenyl<1,2,4>triazolo<4,3-a>quinoxaline 

Relevant academic research and scientific papers

One-pot, two-step synthesis of substituted triazoloquinoxalinone starting from 3-hydrazineylquinoxalin-2(1H)-one

An efficient one-pot two-step synthesis of substituted-triazolo[4,3-a]quinoxalin-4(5H)-one has been developed. The 3-hydrazineylquinoxalin-2(1H)-one reacts with respective aldehyde to afford the individual hydrazineylidene intermediate which undergoes oxidative cyclization in the presence of ferric chloride hexahydrate (FeCl3.6H2O) to affords various substituted- triazolo[4,3-a]quinoxalin-4(5H)-one in good to excellent yields.

Design, synthesis and photoinduced DNA cleavage studies of [1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones

An expedient and eco-friendly synthesis of 1-aryl/heteroaryl-[1,2,4]-triazolo[4,3-a]quinoxalin-4(5H)-ones (4) has been accomplished via iodobenzene diacetate mediated oxidative intramolecular cyclization of 3-(2-(aryl/heteroarylidene)hydrazinyl)-quinoxalin-2(1H)-ones (3). Ten synthesized compounds 3 and 4 (10–40 μg) on irradiation with UV light at λmax 312 nm could lead to cleavage of supercoiled pMaxGFP DNA (Form I) into the relaxed DNA (Form II) without any additive. Further, DNA cleaving ability of triazoles was quantitatively evaluated and was found to be dependent on its structure, concentration, and strictly on photoirradiation time. Mechanistic investigations using several additives as potential inhibitors/activator revealed that the DNA photocleavage reaction involves Type-I pathway leading to formation of superoxide anion radicals (O2 ? [rad]) as the major reactive oxygen species responsible for photocleavage process.

HMPA mediated one pot synthesis of 1-alkyl/aryl-4-dimethylamino[1,2,4]triazalo[4,3-a]quinoxalines

o-Phenylenediamine 1 is condensed with oxalic acid using Phillips' procedure to obtain quinoxaline-2, 3-dione 2. The latter on treatment with hydrazine hydrate gives the known 2-hydrazinoquinoxalin -3-one 3. Reaction of 3 with various acid chlorides (which were obtained from the corresponding carboxylic acids by reaction with thionyl chloride in the presence of catalytic amount of dimethyl formamide) in HMPA medium at 220°C in one pot reaction yield the corresponding 1-substituted-4-dimethylamino[1, 2, 4]triazolo[4, 3-a]quinoxalines 4. This reaction has been shown to proceed through the intermediacy of 2-(N-acyl/aryl hydrazinoquinoxalin -3-one 5 and 1-substituted-4-oxo-[1, 2, 4] triazolo[4, 3-a]quinoxalines 6. An interesting observation here has been that 5 can be cyclised to 6 at a considerably lower temperature of 100°C than the requisite 220°C using catalytic amount of HCl.

Formation of 1-phenyl-4-oxo [1,2,4]triazolo[4,3-a]quinoxaline from 2- chloro-3-(2'-benzylidenehydrazino)quinoxaline during dehydrogenative cyclisation using cupric acetate

Attempted dehydrogenative cyclisation of 2-chloro-3-(2'- benzylidinchydrazino)quinoxaline 5 with a view to prepare 1-phenyl-4-chloro- [1,2,4]-triazolo [4, 3-a]quinoxaline 6 using cupric acetate gives 1-phenyl-4- oxo-[1,2,4]triazolo[4,3-a]quinoxaline 7. A rational explanation is offered for this reaction and the applicability of cupric acetate as dehydrogenative cyclisation agent (such as in the conversion of 10→11) has been demonstrated.