Synthesis of novel N-sulfonyl monocyclic beta-lactams as potential antibacterial agents.
New cis monocyclic beta-lactams were synthesized by [2+2] Staudinger cycloaddition reactions of the imine (3,4-dimethoxybenzylidene)-(4-methoxyphenyl)-amine and ketenes derived from different acyl chlorides and Et3N. These monocyclic beta-lactams were then cleaved by ceric ammonium nitrate (CAN) to give NH-monocyclic beta-lactams, which in turn were converted to N-sulfonyl monocyclic beta-lactams by treatment with four different sulfonyl chlorides in the presence of Et3N and 4,4-dimethyl-aminopyridine (DMAP).
Jarrahpour
Aliasghar
A
Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran. jarrah@susc.ac.ir
Zarei
Maaroof
M
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D008954:Models, Biological; D008968:Molecular Conformation; D008997:Monobactams / Q000138:chemical synthesis* / Q000737:chemistry
D000900:Anti-Bacterial Agents; D008997:Monobactams