4701-01-3

Upstream product

• 6641-64-1 4,5-dichloro-2-nitroaniline 
• 170806-27-6 4,5-dichloro-2-nitrophenylazide 
• 2150-93-8 N-(3,4-dichlorophenyl)acetamide 
• 5462-30-6 N-(4,5-dichloro-2-nitrophenyl)acetamide 
• 95-76-1 m,p-dichloroaniline 
• 89-69-0 2,4,5-Trichloronitrobenzene 

Downstream Products

• 170806-10-7 6,7-dichloro-2-methyl-3-methylthioquinoxaline 1,4-dioxide 
• 170806-11-8 6,7-dichloro-2-methyl-3-phenylthioquinoxaline 1,4-dioxide 
• 170806-12-9 6,7-dichloro-2-methyl-3-(4-chlorophenyl)thioquinoxaline 1,4-dioxide 
• 60680-42-4 (6,7-dichloro-1,4-dioxy-3-phenyl-quinoxalin-2-yl)-phenyl-methanone 
• 934682-02-7 6,7-dichloro-3-methyl-2-(4'-nitrobenzoyl)-quinoxaline 1,4-dioxide 
• 1158081-56-1 C₂₃H₁₆Cl₂N₂O₅ 
• 1158081-54-9 C₂₁H₁₀Cl₄N₂O₃ 
• 1228550-65-9 6,7-dichloro-1,4-di-N-oxide-3-methylquinoxaline-2-carboxylic acid 2-benzylamide 
• 1228550-74-0 6,7-dichloro-1,4-di-N-oxide-3-methylquinoxaline-2-carboxylic acid 2-(4-methoxybenzyl)-amide 
• 1297593-79-3 2-benzoyl-3-(difluoromethyl)-6,7-dichloroquinoxaline-1,4-dioxide 
• 15944-71-5 5,6-dichloro-benzo[1,2,5]oxadiazole 

Relevant academic research and scientific papers

Fast preparation of benzofuroxans by microwave-assisted pyrolysis of o-nitrophenyl azides

Microwave-assisted pyrolysis of o-nitrophenyl azides gives benzofuroxans in good yields in short reaction times.

Generation of benzofuroxans by photolysis of crystalline o-nitrophenylazides. A green chemistry reaction

Several benzofuroxans were obtained by photolysis of crystalline o-nitrophenylazides at ambient temperature. In this particular case, the solid matrix favored the elimination of nitrogen and exclusive formation of heterocyclic benzofuroxan. However, this reaction gives quantitative yields only with crystalline o-nitrophenylazides with a high melting point (above 50 °C).

Discovery of 1,2,3-triazole based quinoxaline-1,4-di-N-oxide derivatives as potential anti-tubercular agents

A series of thirty one novel 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-3-methylquinoxaline-1,4-dioxide (7a-l), 3-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6-chloro-2-methylquinoxaline-1,4-dioxide (8a-l) and 2-(((1-(substituted phenyl)-1H-1,2,3-triazol-4-yl)methoxy)carbonyl)-6,7-dichloro-3-methylquinoxaline-1,4-dioxide (9a-g) analogues were synthesized, characterized using various analytical techniques and single crystal was developed for the compounds 8 g and 9f. Synthesized compounds were evaluated for in vitro anti-tubercular activity against Mycobacterium tuberculosis H37Rv strain and two clinical isolates Spec. 210 and Spec. 192. The titled compounds exhibited minimum inhibitory concentration (MIC) ranging from 30.35 to 252.00 μM. Among the tested compounds, 8e, 8 l, 9c and 9d exhibited moderate activity (MIC = 47.6 – 52.0 μM) and 8a exhibited significant anti-tubercular activity (MIC = 30.35 μM). Furthermore, 8e, 8 l, and 9d were found to be less toxic against human embryonic kidney, HEK 293 cell lines. Finally, a docking study was also performed using MTB DNA Gyrase (PDB ID: 5BS8) for the significantly active compound 8a to know the exact binding pattern within the active site of the target enzyme.

Cu-Catalyzed π-Core Evolution of Benzoxadiazoles with Diaryliodonium Salts for Regioselective Synthesis of Phenazine Scaffolds

The Cu-catalyzed regioselective synthesis of phenazine N-oxides was realized from benzoxadiazoles and diaryliodonium salts. The process was initiated by the electrophilic arylation of benzoxadiazoles with diaryliodonium salts and followed by benzocyclization reactions. The further reduction of N-oxides in situ to phenazine scaffolds and deviation to organic fluorescent materials were readily accomplished.

Radical Chemistry and Cytotoxicity of Bioreductive 3-Substituted Quinoxaline Di-N-Oxides

The radical chemistry and cytotoxicity of a series of quinoxaline di-N-oxide (QDO) compounds has been investigated to explore the mechanism of action of this class of bioreductive drugs. A series of water-soluble 3-trifluoromethyl (4-10), 3-phenyl (11-19)

Effect of complexation of 3-aminoquinoxaline-2-carbonitrile 1,4-dioxides with palladium and copper on their anti-T. cruzi activity

Pd(II) and Cu(II) complexes of 3-aminoquinoxaline-2-carbonitrile 1,4-dioxides were prepared in order to improve the anti-Trypanosoma cruzi activity of these ligands. The in vitro evaluations demonstrated that the metal complexation modified the activity of the ligands in different manners. Except for one compound, complexation with palladium increased the trypanosomicidal activity 20-80-times. Besides, copper also modified favorably the activity, however, the copper compounds resulted less active than the palladium ones, at the studied doses. Springer Science+Business Media, LLC 2011.

Straightforward one-pot synthesis of benzofuroxans from o-halonitrobenzenes in ionic liquids

Treatment of o-halonitrobenzenes with sodium azide in a [empyrr][BF4]/Bu4NBr/H2O system gives benzofuroxans in high yields, with the recovery and reuse of the ionic liquid for at least ten times.

Studies on log Po/w of quinoxaline di-N-oxides: A comparison of RP-HPLC experimental and predictive approaches

As reported in our previous papers, a series of quinoxaline-2-carboxamide 1,4-di-N-oxide derivatives were synthesized and studied as anti-tuberculosis agents. Here, the capability of the shake-flask method was studied and the retention time (expressed as log K) of 20 compounds were determined by RP-HPLC analysis. We found that the prediction of log P by the RP-HPLC analysis can result in a high accuracy and can replace the shake-flask method avoiding the experimental problems presented by quinoxaline di-N-oxides. The studied compounds were subjected to the ALOGPS module with the aim of comparing experimental log Po/w values and predicted data. Moreover, a preliminary in silico screening of the QSAR relationship was made confirming the influence of reduction peak potential, lipophilicity, H-bond donor capacity and molecular dimension descriptors on anti-tuberculosis activity.

Packing similarities of three isosteric molecules: 4,5-Dichlorophthalic anhydride, 4,5-dibromophthalic anhydride and 5,6-dichlorobenzfurazan 1-oxide, including three polymorphs of 5,6-dichlorobenzfurazan 1-oxide

4,5-Dichlorophthalic anhydride (CPA) lies on a twofold axis in space group C2/c; the molecules pack as stacks of two-dimensional sheets. Polymorph A of 5,6-dichlorobenzfurazan 1-oxide (CBF; systematic name 5,6-dichloro-2,1,3-benzoxadiazole 1-oxide) is iso

New hypoxia-selective cytotoxines derived from quinoxaline 1,4-dioxides

A new series of quinoxaline 1,4-dioxides, structurally related to the benzotriazine tirapazamine 1 have been prepared starting from 5,6-dichlorobenzofuroxane 2. The Beirut reaction between 2 and alkyl or aryl thiopropanones afforded the 2-methyl-3-alkyl(a