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Preliminary kinetic investigations 1,2 on substituted N-azaheteroaryl-substituted 2,5- dimethylpyrroles, showed that the relative reactivities of the pyrroles investigated are dependent on the nature of the N-substituent. In order to quantitatively study this influence, we synthesized methyl 2,5-dimethylpyrrole-3-carboxylates, containing as N-substituents a phenyl 9, a 2-pyridyl 10 and a 3-pyridyl 11 group; the β-methoxycarbonyl group was introduced in order to render the pyrrolic substrates amenable to the kinetic measurements. The obtained results support one of the proposed hypotheses.

β-Aminomethylation of N-aryl- and N-azaheteroaryl-substituted methyl 2,5-dimethylpyrrole-3-carboxylates. Kinetic effect of the N-pyrrole substituent