18096-22-5Relevant academic research and scientific papers
Synthesis and selected transformations of 3-oxido-1H-imidazole-4- carboxamides
Mloston, Grzegorz,Jasinski, Marcin
, p. 871 - 885 (2011/05/19)
An efficient synthesis of new N-alkyl- and N-aryl-3-oxido-1H-imidazole-4- carboxamides based on exploration of inexpensive, commercially available ethyl acetoacetate, paraformaldehyde and primary amines is described. Representative compounds were tested in selected transformations, such as 'sulfur-transfer reaction' leading to imidazole-2-thiones and isomerization to corresponding imidazol-2-ones. Strong intramolecular hydrogen bonding via the N-oxide function results in the reduced reactivity of 3-oxido-1H-imidazole-4-carboxamides in both reactions. Moreover, the palladium catalyzed C(2)-arylation of imidazole ring as well as azide-alkyne [3+2] cycloaddition using the N-propargyl substituted 4-carboxamide derived from an imidazole 3-oxide as a dipolarophile, were also studied.
