One-pot three-component catalytic synthesis of fully substituted pyrroles from readily available propargylic alcohols, 1,3-dicarbonyl compounds and primary amines.
A simple and highly efficient method for the preparation of fully substituted pyrroles, from readily accessible secondary propargylic alcohols, 1,3-dicarbonyl compounds and primary amines, has been developed. The one-pot multicomponent reaction, which is catalysed by the system [Ru(eta(3)-2-C(3)H(4)Me)(CO)(dppf)][SbF(6)]/CF(3)CO(2)H (dppf: 1,1'-bis(diphenylphosphanyl)ferrocene), involves initial propargylation of the 1,3-dicarbonyl compound promoted by CF(3)CO(2)H and subsequent condensation between the resulting gamma-keto alkyne and the primary amine to afford a propargylated beta-enamino ester or ketone, which undergoes a ruthenium-catalysed 5-exo-dig annulation to form the final pyrrole.
Cadierno
Victorio
V
Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica, Enrique Moles (Unidad Asociada al CSIC), Universidad de Oviedo, Julián Clavería 8, Oviedo, Spain.
Gimeno
José
J
Nebra
Noel
N
D000438:Alcohols / Q000737:chemistry*; D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004583:Electrons; D021621:Imaging, Three-Dimensional; D008280:Magnetics; D008958:Models, Molecular; D015394:Molecular Structure; D009019:Morphinans / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature
D000438:Alcohols; D000588:Amines; D009019:Morphinans; D011758:Pyrroles