Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on Tertiary Amine Oxides. LVIII. Reactions of Substituted Dehydroquinolizidines with Pyridine N-Oxide. (2)
佐伯 清太郎山下 絢子盛中 泰洋浜名 政和
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1976 年 24 巻 10 号 p. 2509-2516

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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.
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© The Pharmaceutical Society of Japan
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