1.
Chemistry
; 23(71): 18002-18009, 2017 Dec 19.
Artículo
en Inglés
| MEDLINE
| ID: mdl-29024090
RESUMEN
The reactivity of 3-oxo-ß-lactams with respect to primary amines was investigated in depth. Depending on the specific azetidin-2-one C4 substituent, this reaction was shown to selectively produce 3-imino-ß-lactams (through dehydration), α-aminoamides (through CO elimination), or ethanediamides (through an unprecedented C3-C4 ring opening). In addition to the experimental results, the mechanisms and factors governing these peculiar transformations were also examined and elucidated by means of DFT calculations.