106660-45-1

Basic information

• Product Name: 1H-Pyrazolo[3,4-b]quinoxaline, 1-(4-chlorophenyl)-
• CAS NO: 106660-45-1
• Molecular Formula: C15H9ClN4
• Molecular Weight: 280.716
• Mol File: 106660-45-1.mol

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazolo[3,4-b]quinoxaline, 1-(4-chlorophenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazolo[3,4-b]quinoxaline, 1-(4-chlorophenyl)-(106660-45-1)
• EPA Substance Registry System: 1H-Pyrazolo[3,4-b]quinoxaline, 1-(4-chlorophenyl)-(106660-45-1)

Safety Data

• Hazardous Substances Data: 106660-45-1(Hazardous Substances Data)

Upstream product

• 112032-32-3 2-formylquinoxaline oxime 
• 1073-69-4 N-4-chlorophenylhydrazine 
• 20265-96-7 p-chloroaniline hydrochloride 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 
• 109002-25-7 quinoxaline-2-carboxaldehyde p-tolylhydrazone 
• 1593-08-4 Quinoxaline-2-carboxaldehyde 
• 109002-26-8 quinoxaline-2-carboxaldehyde p-chlorophenylhydrazone 
• 33920-28-4 1-phenyl-1H-pyrazolo<3,4-b>quinoxaline 
• 106660-42-8 N-(4-Chloro-phenyl)-N'-[1-(3-chloro-quinoxalin-2-yl)-meth-(E)-ylidene]-hydrazine 
• 106684-91-7 3-Formyl-2-oxo-1,2-dihydroquinoxaline p-Chlorophenylhydrazone 

Downstream Products

• 128499-80-9 1-p-chlorophenyl-3-chloro-1H-pyrazolo<3,4-b>quinoxaline 
• 128499-82-1 2-p-chloroanilinoquinoxaline-3-carboxylic acid 
• 128499-83-2 2-p-chloroanilinoquinoxaline 
• 128499-81-0 2-p-chloroanilinoquinoxaline-3-carboxamide 

Relevant articles and documents

Quinoxalines X [1]. A new and convenient synthesis of 1H-pyrazolo[3,4-b]quinoxalines (flavazoles)

Quinoxaline-2-aldoximes and -ketoximes (6) react with hydrazine, alkylhydrazines or arylhydrazines under acidic conditions to afford 1H-pyrazolo[3,4-b]quinoxalines (flavazoles) (1). Since the oximes (6) are easily available from phenylenediamine, the herein described methodology provides a convenient two step entry to various functionalized flavazoles. Furthermore, acylation and alkylation of the 1-unsubstituted 1H-pyrazolo[3,4-b]quinoxalines 7 proceeds smoothly and in good yield to afford 31 different flavazoles 11 and 12.

A Convenient Synthesis and Antifungal Activity of 1-Aryl-1H- and 1-Aryl-3-heteroaryl-1H-pyrazoloquinoxalines

Novel 1-aryl-1H- and 1-aryl-3-heteroaryl-1H-pyrazoloquinoxalines (flavazoles) 9a-c, 12, 13 were synthesized from 3-methyl-2-oxo-1,2-dihydroquinoxaline 5 and the 3-triazolylmethylene-2-oxo-1,2,3,4-tetrahydroquinoxaline 6, respectively, via a facile hydrazone synthesis using aryl diazonium salts.Some of the above flavazoles and their related compounds exhibited the antifungal activity in some extent.The above results are described.

A Facile Synthesis of Novel 1-Aryl-1H-pyrazoloquinoxalines

The reactions of 3-methyl-2-oxo-1,2-dihydroquinoxaline 3 with chlorophenyl diazonium salts afforded the hydrazones 4a-c, whose chlorinations with phosphoryl chloride gave the dichlorides 5a-c.Refluxing of the dichlorides 5a-c and base in N,N-dimethylformamide provided the 1-aryl-1H-pyrazoloquinoxalines 6a-c.

Phenylation and Dephenylation Reactions: Formation of 1H-Pyrazoloquinoxalines

1,3-Diphenyl-1H-pyrazoloquinoxaline (9) has been isolated as a byproduct in the conversion of quinoxaline-2-carboxaldehyde phenylhydrazone (1) into 1-phenyl-1H-pyrazoloquinoxaline (5) using stored phenylhydrazine as the dehydrogenating agent