title: Smiles rearrangements in Ugi- and Passerini-type couplings: new multicomponent access to O- and N-arylamides.
abstract: 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.
authors: Laboratoire Chimie et procédés, UMR 7652, Ecole Nationale Supérieure de Techniques Avancées, 32 Bd Victor, Paris 75015, France. laurent.elkaim@ensta.fr
authors: Laurent El
authors: LE
authors: Kaïm
authors: Marie
authors: M
authors: Gizolme
authors: Laurence
authors: L
authors: Grimaud
authors: Julie
authors: J
authors: Oble
mesh_terms: 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
chemical_list: D000577:Amides; D006571:Heterocyclic Compounds; D009596:Nitrophenols; D011725:Pyridines; C014047:hydroxypyridines