Nitroimidazoles. <b>IX</b>. Synthesis of 2‐acetyl‐1‐methyl‐5‐nitroimidazole

Abstract

Abstract Manganese dioxide oxidation of 2‐hydroxymethyl‐1‐methyl‐5‐nitroimidazole (6) gave 1‐methyl‐5‐nitroimidazole‐2‐carboxaldehyde (7) in high yield. Reaction of diazomethane with 7 afforded the title compound 1 in low yield. Treatment of ethyl acid malonate with two equivalents of isopropylmagnesium bromide in THF and subsequent addition to 1‐methyl‐5‐nitroimidazole‐2‐carbonylimidazolide (12) yielded ethyl (1‐methyl‐5‐nitroimidazole‐2‐carbonyl)acetate (10) in 70% yield. Hydrolysis and decarboxylation of compound 10 gave the desired compound 1 in 97% yield.