Studies on 1-Azabicyclo Compounds. XII. Synthesis of 5, 6, 8, 9, 10, 11, 11a, 12-Octahydroindolo [3, 2-b] quinolizine and Related Compounds
1972 年 20 巻 8 号 p. 1745-1751
詳細
1972 年 20 巻 8 号 p. 1745-1751
Monoester of benzylmalonic acid (I) and 3-carboxy-4-octahydroquinolizinone (V) were coupled with benzenediazonium salt to yield labile phenylhydrazones, Iia and VII, respectively. IIa was kept standing in chloroform or heated to give another phenylhydrazone (IIb). VIa was similarly converted into VIb. The condensed four-cyclic compound (VIIIa) derived from VIa or VIb was heated with hydrochloric acid and the resulting product (IXa) was subjected to Pictet-Spengler reaction by formalin to afford octahydroindolo [3, 2-b] quinolizine (Xa). Xa was also obtained by reduction of VIIIa with LAH. Treatment of IXa with benzaldehyde in aqueous hydrochloric acid produced XII. Some methoxyl derivatives (VIIIb, Xb) were obtained according to the same route as mentioned above.
