139325-86-3

Upstream product

• 104-94-9 4-methoxy-aniline 
• 5437-98-9 4'-methoxyacetoacetanilide 
• 108-74-7 1,3,5-trimethyl-1,3,5-triazacyclohexane 
• 726-11-4 2-(hydroxyimino)-3-oxo-N-(4-methoxyphenyl)butanamide 
• 50-00-0 formaldehyd 
• 74-89-5 methylamine 

Downstream Products

• 1307308-72-0 methyl [4-(4-bromophenylcarbamoyl)-1,5-dimethyl-1H-imidazol-2-yl]acetate 

Relevant academic research and scientific papers

Straightforward access to (imidazol-2-yl)acetates by reaction of 2-unsubstituted imidazole 3-oxides with dimethyl acetylenedicarboxylate

A new method for the preparation of 1,4,5-trisubstituted (imidazol-2-yl)acetates, based on the reaction of the corresponding imidazole 3-oxides with dimethyl acetylenedicarboxylate (DMAD) is described. Formation of the products is rationalized by a formal 1,3-dipolar cycloaddition and subsequent oxaloyl cleavage. 1,4,5-Trisubstituted imidazole 3-oxides bearing an electron-withdrawing substituent at C(4), easily react with dimethyl acetylenedicarboxylate (DMAD), yielding the corresponding oxobutanoates, which subsequently, in a one-pot procedure undergo hydrolysis through an "oxaloyl cleavage" mode. New (imidazol-2-yl)acetates were isolated in high yields. Copyright