Studies on tertiary amine oxides. 58. Reactions of substituted dehydroquinolizidines with pyridine N-oxide. (2).
作者:SEITARO SAEKI、AYAKO YAMASHITA、YASUHIRO MORINAKA、MASATOMO HAMANA
DOI:10.1248/cpb.24.2509
日期:——
In order to introduce 2-pyridyl group into the 9 position of 1, 1-disubstituted quinolizidine, N-benzoyloxypyridinium chloride (1) was treated with 9-dehydro-1-oxoquinolizidine (3), dehydro-1-ethoxycarbonyl-1-hydroxyquinolizidine (13) and 9-dehydro-1, 1-ethylenedioxyquinolizidine (16) in dichloromethane, followed by reduction of the reactants with sodium borohydride in anhyd. ethanol. Although reactions with 3 and 13 gave no satisfactory result, that with 16 afforded the expected 1, 1-ethylenedioxy-9-(2-pyridyl)-quinolizidine (18) in 17% yield together with dehydro-1, 1-ethylenedioxy-x-(2-pyridyl)-quinolizidine (19). Other observations encountered in reactions of 1 with 3 or 13 as well as in transformation of 2 into 13 and 16 were also described in some detail.
为了将2-吡啶基团引入1,1-二取代喹啉啶的9位,氯苯甲氧基吡啶铵(1)与9-去氢-1-氧喹啉啶(3)、去氢-1-乙氧羰基-1-羟基喹啉啶(13)和9-去氢-1,1-乙烯二氧喹啉啶(16)在二氯甲烷中反应,随后在无水乙醇中用硼氢钠还原反应物。虽然与3和13的反应没有得到令人满意的结果,但与16的反应得到了预期的1,1-乙烯二氧-9-(2-吡啶基)-喹啉啶(18),产率为17%,同时得到了去氢-1,1-乙烯二氧-x-(2-吡啶基)-喹啉啶(19)。与3或13的反应以及将2转化为13和16的过程中遇到的其他观察也被详细描述。