S. Kano, Tsutomu Ebata, S. Shibuya*
Oct 25, 1979
Citations
0
Influential Citations
13
Citations
Journal
Chemical & Pharmaceutical Bulletin
Abstract
Treatment of 4-hydroxymethyl-1-phenylazetidin-2-ones (2a) and (2b) with methanesulfonic acid afforded 4-anilino-2-oxo-tetrahydrofurans (3a) and (3b), respectively. In a similar way, 3-(2-hydroxybenzyl)-1-phenylazetidin-2-one (8), 1-(4-methoxyphenyl)-4-(2-piperidino) azetidin-2-one (13), 3-(2-aminobenzyl)-1-phenylazetidin-2-one (16) and 1-(4-methoxyphenyl)-3-(2-piperidinomethyl) azetidin-2-one (19) were subjected to cleavage of the amide bond to give the corresponding lactone and lactams (9), (14), (17) and (20), respectively. The amide bond of β-lactams was also found to be cleaved by alkyl lithium in the presence of N, N, N', N'-tetramethylethylenediamine to give β-aminoketones.