111232-63-4

Basic information

• Product Name: 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one
• Synonyms: 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one
• CAS NO: 111232-63-4
• Molecular Weight: 290.321
• Mol File: 111232-63-4.mol

Chemical Properties

• CAS DataBase Reference: 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one(111232-63-4)
• EPA Substance Registry System: 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one(111232-63-4)

Safety Data

• Hazardous Substances Data: 111232-63-4(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 88-74-4 2-nitro-aniline 
• 480-96-6 benzofurazan oxide 
• 61522-56-3 3-Acetyl-2-methylquinoxaline 1-Oxide 
• 13297-17-1 3-methyl-2-acetylquinoxaline-1,4-dioxide 
• 81810-66-4 1-(3-methyl-1,4-dioxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one 

Relevant articles and documents

Convenient synthesis of quinocetone metabolites: Characterization, theoretical investigation, and cytotoxicity study

Quinocetone (3-methyl-2-quinoxalinbenzenevinylketo-1,4-dioxide; QCT) is a new promising antimicrobial growth promoter for quinoxalines. The identification of the major metabolites of QCT has resulted in a number of studies regarding its metabolic pathway.

Synthesis of the possible metabolites of quinocetone in animals

The possible metabolites of quinocetone in animals had been prepared with different selective reagent by three synthetic routes. It was their principal reaction that Na2S2O4 reduced quinoxaline-1,4-dioxide derivatives to quinoxaline derivatives, H 2O2 s oxidized 2-carboxyl-quinoxaline derivatives to 2-carboxyl-quinoxaline-1 -oxide ones and P(OCH3) 3 reduced 2-carboxyl- quinoxaline-1,4-dioxide derivatives to 3-carboxyl-quinoxaline-1-oxide ones. The title compounds ware confirmed with NMR,UV, FAB-MS, et al.

Improved synthesis of quinocetone and its two deoxy metabolites

Oxidation of o-nitroaniline with sodium hypochlorite afforded benzofurazan oxide in 96 % yield, and treatment of benzofurazan oxide with acetylacetone in the presence of triethylamine gave 2-acetyl-3-methyl-quinoxaline--1,4-dioxide in 94 % yield. Finally, condensation of 2-acetyl-3-methyl-quinox-aline-1,4-dioxide with benzaldehyde using 4-(dimethylamino)pyridinium acetate as a catalyst led to quinocetone in 95 % yield. Subsequently, reduction of the synthesized quinocetone with sodium dithionite resulted in two deoxy derivatives, 1-(3-methyl-4-oxido-2-quinoxalinyl)-3-phenyl-2-propen-1-one and 1-(3-methyl-2-quinoxalinyl)-3-phenyl-2-propen-1-one in 88.5 and 92 % yield, respectively. Furthermore, the synthesized quinocetone, and its deoxy derivatives were characterized by1H-NMR,13C-NMR and elemental analysis.

REACTIONS OF 2-ACETYL-3-METHYLQUINOXALINE 1,4-DIOXIDE AND ITS DERIVATIVES

2-Cinnamoyl-3-methylquinoxaline 1,4-dioxide (2) was inert to hydrochloric acid in refluxing ethanol.When a xylene solution of 2-acetyl-3-methylquinoxaline 1,4-dioxide (1-dioxide) was refluxed overnight, the dioxide was reduced mainly to 1,4-oxide and the oxidative products from xylene were also obtained. 2-Cinnamoyl-3-methylquinoxaline 4-oxide (4a) and 3-methyl-4-oxido-2-quinoxalyl 4-phenyl-1,3-butadienyl ketone (4b) were quantitatively cyclized into 4-methyl-3-oxo-1-phenyl- and 4-methyl-3-oxo-1-styryl-3H-pyrroloquinoxalin-10-ium chloride (6a and 6 b), respectively , when the ethanolic solution were refluxed in the presence of hydrochloric acid.