1971 年 91 巻 6 号 p. 657-666
8-Unsubstituted-3-oxo-1-thia-4, 8-diazaspiro [4, 5] decane derivatives (V) were prepared from the corresponding 8-alkoxycarbonyl derivatives (IIb, c) by the Method A (HBr-AcOH), method B1 (KOH-iso-PrOH), or method B2 (Claisen's alkali). V were also prepared by the reaction of 4-piperidone hydrochloride (VIII) with corresponding mercapto acids and primary amines (method C). Sulfoxides (VI) of V were prepared by method A or method D1 (oxidation of V with H2O2), and sulfones (VII) were prepared by method A or method D2 (oxidation of V with KMnO4). VI and VII were not obtained by the method B1 or B2. 4-Oxo-1-thia-5, 9-diazaspiro [5, 5] undecane (V-35) was prepared by method A or method C, and the sulfone (VII-25) of V-35 was prepared by method A.