DE-ARYLMETHYLATION OF N-MONO- OR N-DIARYLMETHYL-BETA-LACTAMS; NOVEL AZETIZINONES HAVING ANTI-BACTERIAL ACTIVITY

摘要

beta -Lactams having a hydrogen atom on the nitrogen atom of the beta -lactam ring are prepared by reacting an N-mono-or N-diarylmethyl- beta -lactam with an acid or ceric ammonium nitrate to cleave the bond between the nitrogen atom and the mono- or diarylmethyl group; certain 4-substituted-3-phenylthio -2-azetizinones among the starting and product compounds have anti-bacterial activity. A valuable novel intermediate, 4-(2- phenylethenyl)-3-amino-N-di (p-anisyl) -methyl-2- azetizinone of the formula:

is prepared by reacting an acid anhydride derivative of a compound of the formula:

with a Schiff base of the formula:

and treating the resultant crystalline compound with an acid. The amino group of the product compound is then acylated to form an amido derivative which is subjected to the above dearylmethylation to form an anti-bacterial substance.