42785-83-1Relevant articles and documents
Synthesis of Imidazolidin-2-ones and Imidazol-2-ones via Base-Catalyzed Intramolecular Hydroamidation of Propargylic Ureas under Ambient Conditions
Casnati, Alessandra,Perrone, Antonio,Mazzeo, Paolo P.,Bacchi, Alessia,Mancuso, Raffaella,Gabriele, Bartolo,Maggi, Raimondo,Maestri, Giovanni,Motti, Elena,Stirling, András,Ca, Nicola Della
, p. 3477 - 3490 (2019/03/11)
The first organo-catalyzed synthesis of imidazolidin-2-ones and imidazol-2-ones via intramolecular hydroamidation of propargylic ureas is reported. The phosphazene base BEMP turned out to be the most active organo-catalyst compared with guanidine and amidine bases. Excellent chemo- and regioselectivities to five-membered cyclic ureas have been achieved under ambient conditions, with a wide substrate scope and exceptionally short reaction times (down to 1 min). A base-mediated isomerization step to an allenamide intermediate is the most feasible reaction pathway to give imidazol-2-ones, as suggested by DFT studies.