97934-55-9Relevant academic research and scientific papers
New intramolecular cyclization and rearrangement processes based on the radical aryl-aryl coupling of arylsubstituted 2-azetidinones
Alcaide, Benito,Rodriguez-Vicente, Alberto
, p. 6589 - 6592 (1998)
New polycyclic 2-azetidinones having fused or not biaryl units are easily prepared by the tin-mediated, intramolecular aryl-aryl radical cyclization of readily available arylsubstituted 2-azetidinones. The regioselectivity and efficiency of the process is
A study of the photochemical isomerization in β-lactam rings
Alcazar, Roberto,Ramirez, Pedro,Vicente, Ruben,Mancheno, Maria J.,Sierra, Miguel A.,Gomez-Gallego, Mar
, p. 511 - 521 (2007/10/03)
The cis to trans or trans to cis photoisomerization of 2-azetidinones (1) is reported. The outcome of the photochemical process is controlled by the substitution on the nitrogen atom and by the ability of the substituents at C3 and C4 positions to stabilise radicals. N-Aryl-2-azetidinones are unreactive even after several hours of UV-light irradiation. N-Alkyl-2-azetidinones cleanly isomerize under the same conditions, providing a smooth procedure for the ring isomerization of β-lactams.
Synthesis of β-lactams from acetic acids and imines induced by phenyl dichlorophosphate reagent
Arrieta,Cossio,Palomo
, p. 1703 - 1712 (2007/10/02)
The development of a practical method for the preparation of vinylamino-β-lactams from Dane salts and Schiff bases is described. Among the reagents known to produce β-lactams from imines and acetic acids, only phenyl dichlorophosphate and 1-methyl-2-chloropyridinium iodide are suitable for the synthesis of vinylamino-β-lactams. Reaction of acetic acids with ethanolimine derivatives promoted by phenyl dichlorophosphate affords oxazolidines instead of β-lactams. Protection of the hydroxyl group as the trimethylsilyl ether in the starting Schiff bases provides a convenient route to the corresponding β-lactams instead of oxazolidines. Some observations on the scope of the method are made.
