Mitteilungen aus dem pharmaceutisch‐chemischen Institute der Universität Marburg. 43. Über Cytisin und Ulexin

Abstract

A. P a r t h e i 1, Ueber Cytisin und Ulexin.Auch bei der Untersuchung des Zwiebelols stellte sich heraus, dafs Allylsulfid nicht zugegen war, da dasselbe i n den zuerst ubergehenden Anteilen hatte enthalten sein mussen, der Kohlenstoffgehalt deraelben jedoch vie1 zu gering is%.Z u s am m en f a s s 11 n g d e r g e w o nn e n en R e s u 1 t a t e.

Attempted Syntheses of Pelletierine

“…The above-mentioned formation of the hydrobromide of 3-ketooctahydropyrrocoline (XII) seemed rather unusual in that amides are not usually thought other examples of this phenomenon in addition to the hydrochloride formation of XII, reported by Loeffler and Kaim (4), we found that 4-ketoquinolizidine (XXI) forms a hydrochloride (39,40); no attempt at salt formation was reported on 3-ketopyrrolizidine (41), and 5-ketooctahydropyrrocoline is not described in the literature. More complex examples of nitrogen-bridgehead lactams that have salt-forming properties are cytisine (XXII) which forms a dihydrochloride (42) [as also does oxycytisine (43)] and lupanine, XXIII, which likewise forms a dihydrochloride (44). We hope to later present a satisfactory explanation of this phenomenon.…”

(−)-Cytisine and Derivatives: Synthesis, Reactivity, and Applications

“…The Hofmann exhaustive degradation of cytisine (−)-1 was investigated originally by Partheil. 87 Spath and Galinovsky 88 studied the degradation of (−)-1 sequentially, each Hofmann degradation being followed by a reduction step. Thus, pyridone 26 was obtained from the pyridone-amines 24 and 25 after two degradation−reduction sequences (Scheme 5).…”

“…The Hofmann exhaustive degradation of cytisine (−)- 1 was investigated originally by Partheil . Spath and Galinovsky studied the degradation of (−)- 1 sequentially, each Hofmann degradation being followed by a reduction step.…”