第3級アミンオキシドに関する研究(第56報)置換デヒドロキノリチジンとピリジンN-オキシドとの反応その1

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Treatment of dehydro-1-methylquinolizidines (IVa and IVb) with the benzoyl chloride-adduct of pyridine N-oxide in dichloromethane followed by reduction of the reactants with sodium borohydride afforded 1-methyl-9-(2-pyridyl) quinolizidine (VI) and 1-methyl-1-(2-pyridy) quinolizidine (VII) in 4.1 and 8.3% yields, respectively. A similar treatment of IV with 4-chloropyridine 1-oxide and subsequent catalytic dechlorination of the products also gave VI and VII in 12.3 and 21.5%, respectively. From the reaction of IV with 2-chloropyridine N-oxide, 1-methyl-1-(4-pyridyl) quinolizidine (IX) was obtained as a sole product. The reaction of 9(10)-dehydro-1-hydroxy-1-methylquinolizidine (V) with pyridine N-oxide was carried out and two stereoisomers (XIa and XIb) of 1-hydroxy-1-methyl-9-(2-pyridyl) quinolizidine were isolated in respective yields of 5.9 and 4.3%. The configuration of these products and related compounds was deduced from infrared and nuclear magnetic resonance spectral examinations.
公益社団法人日本薬学会の論文
1976-04-25