Synthesis of 4-Substituted Monocyclic β-Lactams by a Lewis Acid-mediated Reaction

概要

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The synthesis of 4-substituted monocyclic β-lactam is described. The key step in this method was accomplished by nucleophilic replacement in the presence of Lewis acid, that is, (3S, 4S)-4-acetoxy-3-phenylacetamido-2-azetidinone derivatives or oxazolinoazetidinone derivatives were reacted with nucleophiles (5-mercapto-l-methyltetrazole, 5-methyltetrazole, l-ethyl-2, 3-dioxopiperazine, l-ethyl-4-trimethylsilyl-2, 3-dioxopiperazine) in the presence of Lewis acids (BF3•Et2O, SnCl4, TiCl4, ZnCl2) to afford the title compounds. The antibacterial activities of the compounds thus obtained were compared with those of the reference compound (pyridium (3S)-3-phenylacetamido-2-azetidinone-1-sulfonate).
社団法人日本農芸化学会の論文