New benzotriazole and benzimidazole scaffolds from Ugi-Smiles couplings of isocyanides.
When allylamine is used as the amino input in Ugi-Smiles couplings of o-nitrophenols, the resulting adducts can be deallylated by a palladium-catalyzed process leading to a formal Ugi-Smiles coupling with ammonia. This new sequence, combined with hydrogenolysis of the nitro group, offers an interesting multicomponent entry to benzotriazole and benzimidazole scaffolds.
Coffinier
Didier
D
Laboratoire Chimie et procedes, Ecole Nationale Superieure de Techniques Avancees, 32 Bd Victor, 75739 Paris Cedex 15, France.
El Kaim
Laurent
L
Grimaud
Laurence
L
D000641:Ammonia / Q000737:chemistry; D001562:Benzimidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003486:Cyanides / Q000737:chemistry*; D015394:Molecular Structure; D009596:Nitrophenols / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry
D001562:Benzimidazoles; D003486:Cyanides; D009596:Nitrophenols; D014230:Triazoles; D010165:Palladium; D000641:Ammonia; C012771:benzotriazole