Studies on Azetidine Derivatives. IV. Synthesis and Some Reactions of Azetidin-3-one Derivatives

AKIRA MORIMOTO, TETSUYA OKUTANI, KATSUTADA MASUDA
1973 Chemical and pharmaceutical bulletin  
Although quite an extensive investigation has been done on azetidin-2-ones, only a few papers have been reported on azetidin-3-one derivatives. The compounds which fall in this category are 1-acetyl-2,2,4,4-tetramethylazetidin-3-one,3) 1-benzoylazetidin-3-one4) and 1-t-butyl-2,2-dimethylazetidin-3-one.5) However no direct oxidation of 1-alkyl-azetidin-3-ols6) to the corresponding azetidin-3-ones has been reported. This prompted us to attempt the oxidation of some
more » ... s to the corresponding azetidin-3-ones which might be useful as intermediates in our studies exploring new azetidine derivatives. Treatment of 1-diphenylmethylazetidin-3-ol (Ia)7) with pyridine-SO3 in DMSO and triethylamine for 30 min8) gave 1-diphenylmethylazetidin-3-one (IIa) in good yield. The struc-Chart 1 1) A part of this paper was presented at the 3rd International
doi:10.1248/cpb.21.228 fatcat:e63xgpjfxjd5rgii4vspqs5duu