79456-94-3

Upstream product

• 79456-89-6 1-(4-Bromo-phenyl)-2-(2-methyl-4-nitro-imidazol-1-yl)-ethanone 
• 99-73-0 para-bromophenacyl bromide 
• 18874-52-7 5-bromo-2-methyl-4-nitro-1H-imidazole 
• 204444-55-3 4-bromo-1-(4-bromophenacyl)-2-methyl-5-nitroimidazole 
• 18874-52-7 4-bromo-2-methyl-5-nitroimidazole 

Downstream Products

• 79457-07-1 3-(4-Bromo-phenyl)-6-methyl-8-nitro-1-(4-nitro-phenyl)-1,4-dihydro-imidazo[5,1-c][1,2,4]triazine 
• 79456-99-8 3-(4-Bromo-phenyl)-6-methyl-8-nitro-1,4-dihydro-imidazo[5,1-c][1,2,4]triazine 

Relevant academic research and scientific papers

Tetrabutyl ammonium bromide as a catalyst for reaction of 5(4)-bromo-2-methyl-4(5)-nitroimidazole with phenacyl bromides

Reactions of 5(4)-bromo-2-methyl-4(5)-nitroimidazole with phenacyl bromide, tetrabutylammonium bromide (TBAB) and sodium bicarbonate in the sonication condition resulted in a mixture of 4-bromo-5-nitroimidazoles [IIIa-e] and 5-bromo-4-nitroimidazoles [IVa-e] at an excellent yield of over 85% and, surprisingly, at the isomers ratio of 2:1.

Isomerization of 4-Bromo-2-methyl-5-nitro-1-phenacylimidazoles into 5-Bromo-2-methyl-4-nitro-1-phenacylimidazoles

4-Bromo-2-methyl-5-nitro-1-phenacylimidazoles (1a-e) dissolved in EtOH in presence of sodium bicarbonate (or without it) heated under reflux were isomerized into 5-bromo-2-methyl-4-nitro-1-phenacylimidazoles (5a-e). The structures of 5a-e were assigned using SFORD (Single Frequency Off Resonance Decoupling) and COLOC (Correlation Spectroscopy for Long Range Coupling) NMR techniques. A conceivable mechanism of isomerization is discussed. Wiley-VCH Verlag GmbH, 1999.

Synthesis of some 5-amino-2-methyl-4-nitro-1-phenacylimidazoles

Reaction of 4(5)-bromo-2-methyl-5(4)-nitroimidazole with phenacyl bromide derivatives gave two isomers: 4-bromo-5-nitroimidazoles (4a-e) and 5-bromo-4-nitroimidazoles (5a-e). Compounds 5a-e were treated with cyclic secondary amines to afford expected 5-amino-4-nitroimidazole derivatives 6a-c - 10a-b.

CONDENSED IMIDAZO-1,2,4-AZINES. 4. SYNTHESIS OF 1,4-DIHYDROIMIDAZO-1,2,4-TRIAZINE DERIVATIVES

The reaction of 2-methyl-4(5)-nitro- and 2-methyl-4(5)-nitro-5(4)-bromoimidazoles with α-haloketones was investigated, during which a number of 1-acylmethyl-substituted 2-methyl-4-nitro- and 2-methyl-4-nitro-5-bromoimidazoles were obtained. 1,4-Dihydro de