Synthesis of Quinolizine Derivatives. XI

Synthesis of 3-Substituted Quinolizidine Derivatives. (2). Synthesis of Qulnolizidinylisoquinoline-type Compounds

Abstract

The compounds (I) and (II) were prepared in order to examine uterus-contracting and antibacterial actions. Condensation of ethyl 4-oxo-3-quinolizidinecarboxylate (III) and homoveratrylamine or homopiperonylamine afforded the acid amide compounds (Va and Vb) which were submitted to Bischier-Napieralski cyclization to form 1-substituted 3, 4-dihydroisoquinoline compounds (VIa) and (VIb). Reduction of (VI) with lithium aluminium hydride finally gave (I) and (II). It was found that (III) used as the starting material contained over 80% of axial ethoxycarbonyl group and it was considered that (Va) and (Vb) obtained as only one kind of crystals has an axially bonded side chain.