Synthesis of Quinolizine Derivatives. IX. Synthesis of 3, 3'-Polymethylenediquinolizidine

Abstract

In expectation of a curariform activity with little side effects, methiodide of 3, 3'-polymethylenediquinolizidines (I : n=4, 6, 8, and 10) were synthesized. Condensation of the potassium salt of 3-ethoxycarbony1-4-oxoquinolizidine and polymethylene bromide, followed by saponification and decarboxylation, and reduction with lithium aluminum hydride of the lactam compound so obtained afforded the objective compounds (I). (I : n=4) was also obtained through 3-(4-phenoxybutyl) quinolizidine (IX) as an intermediate and compounds obtained by the two procedures were found to be identical. The curariform activity of (I) (n=4 and 6) was one-quarter that of tubocurarine chloride while their toxicity was 6 and 10 times, respectively, of tubocurarine. The compound with n=10 had a strong antibacterial and antifungal activity.