97111-39-2

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 51347-93-4 2‐chloro‐3‐hydrazinylquinoxaline 
• 97111-31-4 C₂₂H₁₇ClN₆O 
• 2213-63-0 2,3-dichloroquinoxaline 
• 15804-19-0 quinoxaline-2,3-dione 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 97111-30-3 C₂₆H₂₅ClN₆O 
• 97111-46-1 C₂₅H₂₃ClN₆O 
• 97111-29-0 C₂₄H₂₂ClN₇O 
• 97111-32-5 C₂₂H₁₆ClN₇O₃ 
• 97111-31-4 C₂₂H₁₇ClN₆O 
• 97111-33-6 C₂₂H₁₆ClN₇O₃ 
• 226986-35-2 N-(3-Ethoxy-quinoxalin-2-yl)-N'-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazine 
• 97111-56-3 4-Chloro-1-(4-methoxy-phenyl)-[1,2,4]triazolo[4,3-a]quinoxaline 
• 226986-36-3 N-(3-Isopropoxy-quinoxalin-2-yl)-N'-[1-(4-methoxy-phenyl)-meth-(E)-ylidene]-hydrazine 
• 226986-37-4 N-[1-(4-Methoxy-phenyl)-meth-(E)-ylidene]-N'-(3-phenoxy-quinoxalin-2-yl)-hydrazine 

Relevant academic research and scientific papers

Synthesis of pyrrolo[2,3-b]quinoxalines by the Pd/C-catalyzed multicomponent reaction of 1,2-dichloroquinoxaline with hydrazine hydrate, phenylacetylene, and a variety of aldehydes in water

The one-pot, Pd/C-catalyzed, multicomponent reaction of 1,2-dichloroquinoxaline with hydrazine hydrate, phenylacetylene, and a variety of aldehydes provides an efficient and direct method for the preparation of N-substituted pyrrolo[2,3-b]quinoxalines in

Studies in the syntheses of s-triazolo[4,3-a] quinoxalines

o-Phenylendiamine 1 is condensed with oxalic acid using Phillip's procedure to obtain quinoxaline-2,3-doine 2, which on treatment with POCl3 gives the known 2,3-dichloroquinoxaline 3. 2-Chloro-3-hydrazinoquinoxaline 4 is prepared in a facile and simple way by treatment of 3 with hydrazine hydrate in methanol or in dioxane containing triethylamine. Condensation of 4 with a variety of aldehydes in DMF at room temperature furnishes the corresponding arylidene/alkylidine derivatives 5 which undergo smooth nucleophilic substitutions of chlorine by alkoxide or phenoxide ions yielding 2-alkoxy/phenoxy-3-(2-arylidene/alkylidene hydrazino) quinoxalines 6. The dehydrogenative cyclisation of 6 is achieved with chloranil in refluxing 1,2- dichloroethane resulting in s-triazole-[4,3-a] quinoxalines 7 whose structures are supported by spectral and analytical data and by alternate chemical synthesis in the case of the parent compound 7a.

INVESTIGATION OF THE DECOMPOSITION OF 1,3-DIARYL-5-(3-CHLORO-2-QUINOXALYL)-FORMAZANS BY PMR AND MASS SPECTROMETRY

In contrast to triarylformazans, 1,3-diaryl-5-(3-chloro-2-quinoxalyl)formazans are unstable in ordinary organic solvents.When they are heated in chloroform, they undergo acidic cleavage, which leads to the formation of 3-chloro-2-quinoxalylhydrazones of p-substituted benzaldehydes and arenediazonium cations.These compounds, as a result of a redox reaction with the participation of the solvent, are converted to 4-chloro-1-(4-Y-phenyl)-1,2,4-triazoloquinoxalines, substituted benzenes, nitrogen, and hydrogen chloride.The formation of the latter transforms the entire decomposition process into an autocatalytic process.Effects of chemical polarization of the nuclei (CPN), which unambiguously indicate the intermediate formation of diazoaryl radicals during the process, are observed in the PMR spectra of the final products.Such CPN effects, which were also observed in dimethyl sulfoxide (DMSO) and glacial acetic acid, indicate a process involving the oxidative formation of annelated triazoles from α-azahetarylhydrazones via a radical pathway within a solvent "cage."

STRUCTURE OF QUINOXALYFORMAZANS IN SOLUTION

1(5),3-Diaryl-5(1)-quinoxalylformazans in the solid phase exist in the chelate syn-s-cis-trans conformation, whereas in solutions in CCl4 and CH(D)Cl3 they exist in the form of equilibrium mixtures of chelate and open forms.The percentage and conformation