title: Reactions of in situ generated N-Boc nitrones with aromatic and heteroaromatic grignard reagents: application to the synthesis of zileuton.
abstract: A new class of alpha-aromatic-N-hydroxylamines has been prepared by reaction of tert-butyl (phenylsulfonyl)alkyl-N-hydroxycarbamates with aromatic and heteroaromatic Grignard reagents. Reactions proceed via a base-assisted elimination of the phenylsulfonyl group leading to N-Boc nitrones. This methodology has been applied to the synthesis of zileuton.
authors.affiliation: Département de Chimie Moléculaire SERCO, UMR-5250, ICMG FR-2607, CNRS, Université Joseph Fourier, BP-53, 38041 Grenoble Cedex 9, France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Guinchard
authors.forename: Jean-Noël
authors.initials: JN
authors.lastname: Denis
mesh_terms: D006918:Hydroxyurea / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*
chemical_list: D007202:Indicators and Reagents; D009589:Nitrogen Oxides; C015388:nitrones; C063449:zileuton; D006918:Hydroxyurea