Studies on piperidine derivatives. 3. Studies on the synthesis of 3-oxo-1-thia-4,8-diazaspiro [4,5] decane derivatives. (1)

Abstract

3-Oxo-1-thia-4, 8-diazaspiro [4, 5] decane derivatives (IV, VI) were prepared from 1-substituted 4-piperidones (I), primary amines (II-1, R2=H ; II-2, R2=alkyl ; II-3, R2=arylalkyl ; II-4, R2=aryl), and mercapto acids (III-1, A=-CH2- ; III-3, A=-(CH3)CH- ; III-4, A=-(C6H5)CH- ; III-5, A=-(CH3)2C- ; III-6, A=-(C6H5)2C-). Similarly, 4-oxo-1-thia-5, 9-diazaspiro [5, 5] undecane derivatives (VII) were prepared, though in low yields, from I, II-1, and 3-mercaptopropionic acid (III-2), but corresponding products were not obtained from I, II-2-II-4, and III-2. Sulfoxides (XI) and sulfones (XII) of IV, VI, and VII were also prepared. Reaction condition, byproducts and reaction mechanism were briefly examined.