Smiles rearrangements in Ugi- and Passerini-type couplings: new multicomponent access to O- and N-arylamides.
The use of Smiles rearrangement in Ugi- and Passerini-type couplings with electron-deficient phenols allows very straightforward multicomponent formation of O-aryl- and N-arylamides. Best yields were observed with the highly activated o- and p-nitrophenols, salicylic derivatives giving adducts in lower yields. The scope of these new reactions is further increased by the successful couplings of heterocyclic phenols such as hydroxypyridines and hydroxypyrimidines.
Kaïm
Laurent El
LE
Laboratoire Chimie et procédés, UMR 7652, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, Paris 75015, France. laurent.elkaim@ensta.fr
Gizolme
Marie
M
Grimaud
Laurence
L
Oble
Julie
J
D000577:Amides / Q000138:chemical synthesis*; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D015394:Molecular Structure; D009596:Nitrophenols / Q000737:chemistry*; D011725:Pyridines / Q000737:chemistry*; D013237:Stereoisomerism
D000577:Amides; D006571:Heterocyclic Compounds; D009596:Nitrophenols; D011725:Pyridines; C014047:hydroxypyridines