Schiff塩基と無水ジクロル酢酸の反応について (第2報)

抄録

The reaction of the Schiff bases of β-amino alcohols with dichloroacetic anhydride was examined. While the Schiff base of alkanolamines underwent oxazolidine cyclization reaction, the Schiff base of aralkanolamines, having phenyl, benzyl, or phenethyl group in the 2-position of ethanolamine, underwent β-lactam cyclization. On the other hand, the Schiff base (VIII) of aralkanolamines, with a phenyl group in 1-position underwent oxazolidine cyclization, and the Schiff base (XXII) of that with a phenyl group in 1-position and methyl group in 2-position underwent β-lactam cyclization. D-threo-1-(p-Nitrophenyl)-2-benzylideneamino-1, 3-propanediol (XXVII) underwent neither oxazolidine nor β-lactam cyclization by reaction with dichloroacetic anhydride but formed chloramphenicol (XXX) and its bis (dichloroacetate) (XXIX).