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Report | Regular issue | Vol 16, No. 12, 1981, pp.2159-2167
Published online, 1st January, 1970
DOI: 10.3987/R-1981-12-2159
Synthesis and NMR Study of Mannich Bases of 8-Acetoxy-indolizines

Henri Sliwa* and Dominique Blondeau

*Laboratoire de Chimie Organique et Environnement, Université des Sciences et Technologies de Lille, Bat. C4 -2eme Etage, 59655 Villeneuve d’ Ascq Cedex, France

Abstract

Crystallized hydrochlorides of some unstable Mannich bases derived from 8-acetoxyindolizine (1) and 3-acetyl-8-acetoxyindolizine (3) have been prepared by condensation of iminium salts on these substrates. The nmr study of the free bases and their hydrochlorides shows the selectivity of the reaction which introduces the aminomethyl side chain at positions 3 in 1 and 1 in 3. The disappearance of the strong deshielding observed for H-5, in the 3-acetyl series, when one passes from the free base to the corresponding hydrochloride is discussed in terms of restricted rotation and dipolar interactions.