title: Metalation of 4-oxazolinyloxazole derivatives. A convenient route to 2,4-bifunctionalized oxazoles.
abstract: The synthesis of an array of 5-phenyloxazole derivatives bearing a variety of hydroxyalkyl groups at the C-2 position of the heterocyclic nucleus and possessing a formyl or a carboxyl function at C-4 is reported. These bifunctionalized compounds have been efficiently prepared by addition of carbonylated electrophiles to the 2-lithio derivative of 5-phenyloxazole preliminarily equipped with an oxazoline unit at the 4-position of the oxazole nucleus. It is demonstrated that this protocol offers a double advantage since it suppresses the troublesome electrocyclic ring-opening reaction and allows access to the target compounds by simple chemical transformation of the oxazoline ring system.
authors.affiliation: Laboratoire de Chimie Organique Physique, UPRES A-CNRS 8009, Université des Sciences et Technologies de Lille, F-59655 Villeneuve d'Ascq Cedex, France. axel.couture@univ-lille.fr
authors.forename: Axel
authors.initials: A
authors.lastname: Couture
authors.forename: Pierre
authors.initials: P
authors.lastname: Grandclaudon
authors.forename: Christophe
authors.initials: C
authors.lastname: Hoarau
authors.forename: Joséphine
authors.initials: J
authors.lastname: Cornet
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Hénichart
authors.forename: Raymond
authors.initials: R
authors.lastname: Houssin
mesh_terms: D004791:Enzyme Inhibitors / Q000138:chemical synthesis; D008094:Lithium / Q000737:chemistry*; D010080:Oxazoles / Q000138:chemical synthesis*
chemical_list: D004791:Enzyme Inhibitors; D010080:Oxazoles; D008094:Lithium