1137089-70-3Relevant academic research and scientific papers
Regioselective N-alkylation of imidazo[4,5-b]pyridine-4-oxide derivatives: an experimental and DFT study
Zeinyeh, Wael,Pilmé, Julien,Radix, Sylvie,Walchshofer, Nadia
, p. 1828 - 1833 (2009)
Regioselectivities were determined for N-alkylations of imidazo[4,5-b]pyridine-4-oxide and 2-methyl-imidazo[4,5-b]pyridine-4-oxide with benzyl bromide or benzyl iodide at RT using K2CO3 in DMF as a base. Experimental attempts have shown that N-1/N-3 ratios slightly varied according to the substitution on C-2 position. This was confirmed by DFT calculations in solvent phase. This computational study has shown first that this N-benzylation reaction passed through a SN2 mechanism. Moreover, regioselectivity of N-benzylation has appeared essentially governed by 'steric approach control'. It explained that opposite N-1/N-3 ratios were obtained with imidazo[4,5-b]pyridine-4-oxide and its 2-methyl-substituted analog. Finally, regioselectivities slightly varied with the nature of benzyl halide.
