97111-40-5

Upstream product

• 2213-63-0 2,3-dichloroquinoxaline 
• 100-52-7 benzaldehyde 
• 51347-93-4 2‐chloro‐3‐hydrazinylquinoxaline 
• 95-54-5 1,2-diamino-benzene 
• 15804-19-0 quinoxaline-2,3-dione 

Downstream Products

• 97111-34-7 C₂₅H₂₃ClN₆ 
• 226986-42-1 N-(3-Ethoxy-quinoxalin-2-yl)-N'-[1-phenyl-meth-(E)-ylidene]-hydrazine 
• 91895-65-7 4-chloro-1-phenyl<1,2,4>triazolo<4,3-a>quinoxaline 
• 129227-28-7 1-phenyl-[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one 
• 226986-44-3 N-(3-Phenoxy-quinoxalin-2-yl)-N'-[1-phenyl-meth-(E)-ylidene]-hydrazine 
• 226986-43-2 N-(3-Isopropoxy-quinoxalin-2-yl)-N'-[1-phenyl-meth-(E)-ylidene]-hydrazine 
• 226986-41-0 N-(3-Methoxy-quinoxalin-2-yl)-N'-[1-phenyl-meth-(E)-ylidene]-hydrazine 
• 97111-35-8 C₂₁H₁₅ClN₆ 

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

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.

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.

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