Reductive C-alkylation. II
- 1 January 1970
- journal article
- Published by Canadian Science Publishing in Canadian Journal of Chemistry
- Vol. 48 (1) , 139-143
- https://doi.org/10.1139/v70-019
Abstract
Methylpyrrole carboxylic esters generally are reductively methylated at 25–45°. Some are also reductively alkylated by aliphatic aldehydes generally to give, for example, 2,3(or 2,4)-dimethyl-4(or 3)-alkyl-5-carbethoxypyrroles, using hydriodic acid or HCl/AcOH–Zn/Hg respectively. An analogous alkylation by glyoxylic acid gave 5-carbethoxyhemopyrrole-dicarboxylic ester. Using HI, paraldehyde at 100° gave diethyl derivatives of dimethylpyrroles, and aminoacetal at 35° converted 2,4-dimethyl-3-acetylpyrrole into its 5-(2-amino-ethyl)-derivative. Reductive alkylations have been most useful with pyrroles but HI converted 2-biphenylcarbaldehyde into fluorene.Keywords
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