The AlCl3-promoted reaction of methyl 2,5-dimethylpyrrole-1-carboxylate 1 with dimethyl acetylenedicarboxylate affords under certain conditions a low yield of 2,5-dimethyl-2-tricarbomethoxyvinyl-2H-pyrrole 3. The structure of the latter was established on the basis of detailed 1H and 13C nmr studies, and confirmed by conversion to dimethyl 5-methyl-5-(3-oxobutyl)-3-pyrrolin-2-one-3,4-dicarboxylate 4.

AlCl3-promoted reaction of 1-carbomethoxy-2,5-dimethylpyrrole with dimethyl acetylenedicarboxylate leads to the formation of 2,5-dimethyl-2-tricarbomethoxyvinyl-2H-pyrrole 3.

Canadian Journal of Chemistry

An unusual carbomethoxyl migration from nitrogen to carbon. Formation of a 2H-pyrrole from AlCl3-promoted reaction of 1-carbomethoxy-2,5-dimethylpyrrole with dimethyl acetylenedicarboxylate

Paper

An unusual carbomethoxyl migration from nitrogen to carbon. Formation of a 2H-pyrrole from AlCl3-promoted reaction of 1-carbomethoxy-2,5-dimethylpyrrole with dimethyl acetylenedicarboxylate

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