Synthesis of some hydroxymethyl- and aminomethyl-indolizines

Journal of the Chemical Society C: Organic Pub Date: DOI: 10.1039/J39690000901

Abstract

Syntheses are reported of 2-hydroxymethylindolizine (4), 3-hydroxymethylindolizine (5), and 2-methyl-6-hydroxymethylindolizine (6). Attempts to prepare 1-hydroxymethyl-2-methylindolizine by reduction of the corresponding ethoxycarbonyl derivative or by a Chichibabin synthesis from a 2-pyridylethanol derivative were unsuccessful, although 1-(2-hydroxyethyl)-2-methylindolizine (13) was so obtained. The very unstable 2-aminomethyl-indolizine (15) and 7-aminomethyl-2-methylindolizine (34) have been obtained by reduction of the corresponding nitriles; attempts to obtain 6-aminomethyl-2-methylindolizine are described.

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