132467-01-7

Basic information

• Product Name: 3-[2-(2-chloro-phenyl)-vinyl]-1H-quinoxalin-2-one
• Synonyms: 3-[2-(2-chloro-phenyl)-vinyl]-1H-quinoxalin-2-one
• CAS NO: 132467-01-7
• Molecular Weight: 282.729
• Mol File: 132467-01-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 3-[2-(2-chloro-phenyl)-vinyl]-1H-quinoxalin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3-[2-(2-chloro-phenyl)-vinyl]-1H-quinoxalin-2-one(132467-01-7)
• EPA Substance Registry System: 3-[2-(2-chloro-phenyl)-vinyl]-1H-quinoxalin-2-one(132467-01-7)

Safety Data

• Hazardous Substances Data: 132467-01-7(Hazardous Substances Data)

Upstream product

• 95-54-5 1,2-diamino-benzene 
• 14003-34-0 3-methyl-2-oxo-1,2-dihydroquinoxaline 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 1022161-40-5 2-chloro-3-(2-(2-chlorophenyl)ethenyl)quinoxaline 
• 366018-68-0 2-Benzenesulfonyl-3-[(E)-2-(2-chloro-phenyl)-vinyl]-quinoxaline 
• 366018-64-6 2-[(E)-2-(2-Chloro-phenyl)-vinyl]-3-phenylsulfanyl-quinoxaline 
• 53047-14-6 2-Chloro-3-[(E)-2-(2-chloro-phenyl)-vinyl]-quinoxaline 

Relevant articles and documents

Malononitrile-activated synthesis and anti-cholinesterase activity of styrylquinoxalin-2(1: H)-ones

Herein, we report a base-free malononitrile activated condensation of 3-methylquinoxaline-2(1H)-one (3MQ) 1 with aryl aldehydes 3a-3ad for synthesis of styrylquinoxalin-2(1H)-ones (SQs) 4a-4ad with excellent yields. In this reaction, malononitrile activates the aldehyde via Knoevenagel condensation towards reaction with 3MQ 1 and gets liberated during the course of reaction to yield the desired SQs 4a-4ad. The SQs were evaluated for in vitro cholinesterase inhibition and 4n was found to display a mixed type of inhibition of AChE, which was supported by molecular modelling studies. This study has led to the discovery of a new chemotype for cholinesterase inhibition which might be useful in finding a remedy for Alzheimer's disease.

Studies on the synthesis of 2-phenylsulphonyl-3-styrylquinoxalines

o-Phenylenediamine 1 is condensed with pyruvic acid or sodium pyruvate to yield 3-methylbenzo-1H-dihydropyrazine-2-one 2. The latter on condensation with aromatic aldehydes give 3-styrylquinoxaline-1H-2-one 3. Reaction of 3 with POCl3 in the presence of catalytic amount of DMF yields 2-chloro-3-styrylquinoxaline 4, which on reaction with thiophenol in the presence of triethylamine in methanol gives 2-phenylthio-3-styrylquinoxaline 5. Oxidation of 5 with H2O2 in the presence of acetic anhydride affords 2-phenylsulphonyl-3-styrylquinoxaline 6. 6 has also been prepared directly from 4 by reaction with sodium benzenesulphinate under phase transfer conditions. In an alternate approach to the synthesis of title compound. 2 is treated with POCl3 in DMF to obtain the known 2-chloro-3-methylquinoxaline 7. Reaction of 7 with thiophenol in the presence of triethylamine in methanol gives 2-methyl-3-phenylthioquinoxaline 8. Oxidation of 8 with H2O2 in Ac2O affords 2-methyl-3-phenylsulphonylquinoxaline 9. 9 was also prepared in an alternate method from 7 by reaction with sodium benzenesulphinate, 9 on reaction with aromatic aldehydes yields the title compounds 6.