New ortho-quinone methide formation: application to three-component coupling of isocyanides, aldehydes and phenols.
Herein, we wish to report a new three-component formation of heterocyclic scaffolds based on a one-pot process from simple phenols. The key step of this procedure involves an ortho-quinone methide formation from Mannich adducts under alkylative conditions. The transient o-quinone methide has been trapped in situ with indole and diketone using lithium perchlorate as catalyst. The interest of this procedure has been furthermore demonstrated by a new three-component aminobenzofuran formation from phenols, aldehydes and isocyanides.
El Kaïm
Laurent
L
Laboratoire de Chimie Organique, UMR CNRS 7652, Ecole Nationale Supérieure des Techniques Avancées, 32, Bd Victor, 75015, Paris, France. laurent.elkaim@ensta.fr
Grimaud
Laurence
L
Oble
Julie
J
D000447:Aldehydes / Q000737:chemistry*; D003486:Cyanides / Q000737:chemistry*; D003500:Cyclization; D045563:Indolequinones / Q000138:chemical synthesis* / Q000737:chemistry; D010636:Phenols / Q000737:chemistry*
D000447:Aldehydes; D003486:Cyanides; D045563:Indolequinones; D010636:Phenols; C068040:quinone methide