13230-22-3

Usage

InChI:InChI=1/C8H11N3O4/c1-3-15-8(12)5-10-4-7(11(13)14)9-6(10)2/h4H,3,5H2,1-2H3

Upstream product

• 105-39-5 chloroacetic acid ethyl ester 
• 696-23-1 2-methyl-4-nitro-1H-imidazole 
• 551-92-8 dimetridazole 
• 105-36-2 ethyl bromoacetate 

Downstream Products

• 93637-70-8 (2-Methyl-4-nitro-imidazol-1-yl)-acetic acid [1-{4-[bis-(2-chloro-ethyl)-amino]-phenyl}-meth-(E)-ylidene]-hydrazide 
• 302807-92-7 5-bromo-1-carboxymethyl-2-methyl-4-nitroimidazole 
• 16230-87-8 1-carboxymethyl-2-methyl-4-nitroimidazole 
• 93637-76-4 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide 
• 72896-08-3 (5-bromo-2-methyl-4-nitro-imidazol-1-yl)-acetic acid ethyl ester 

Relevant academic research and scientific papers

Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus

Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods. Crystal X-ray structures are reported for six compounds.

Convenient syntheses of 5-[(2-Methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3, 4-oxadiazole-2(3H)thione and N-substituted 2-amino-5-[(2-methyl-5-nitro-1H- imidazol-1-yl)methyl]-1,3,4-thiadiazoles

(Chemical Equation Presented) Oxidation of metronidazole (4) with sodium dichromate yielded the corresponding 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetic acid (5) which was esterified with 1-butanol to give butyl 2-(2-methyl-5-nitro- 1H-imidazol-1-yl)acetate (8). Reaction of the latter with hydrazine hydrate gave 2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide (9). Compound 5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione (10) could be obtained through the reaction of compound 9 with carbon disulfide in basic medium. Subsequent alkylation of compound 10 afforded alkyl 2-(5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-oxadiazol-2-ylthio) acetate (11) in good yield. Reaction of hydrazide 9 with substituted isothiocynate yielded 1-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetyl]-4-aryl(or ethyl)thiosemicarbazide (12) which was cyclized in acidic media to N-substituted 2-amino-5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-1,3,4-thiadiazole (13).

Synthesis of 7-methyl-6-(nitroimidazolyl)thiopurines

We have studied the reactions of 7-methyl-6-thiopurine with 5(4)-halo-4(5)-nitroimidazoles and 6-chloro-7-methylpurine with sodium and ammonium salts of 5-mercapto-4-nitroimidazoles. We have obtained a series of 7-methyl-6-(nitroimidazolyl)thiopurines not previously described in the literature.

Solid-liquid phase-transfer catalytic method for N-alkylation of nitroimidazole

A variety of 1-alkyl-2-methyl-4-nitroimidazoles have been synthesized with a solid-liquid phase-transfer catalytic method in excellent yields.