Reactions of in situ generated N-Boc nitrones with aromatic and heteroaromatic grignard reagents: application to the synthesis of zileuton.
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.
Guinchard
Xavier
X
Département de Chimie Moléculaire SERCO, UMR-5250, ICMG FR-2607, CNRS, Université Joseph Fourier, BP-53, 38041 Grenoble Cedex 9, France.
Denis
Jean-Noël
JN
D006918:Hydroxyurea / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D007202:Indicators and Reagents / Q000737:chemistry*; D009589:Nitrogen Oxides / Q000737:chemistry*
D007202:Indicators and Reagents; D009589:Nitrogen Oxides; C015388:nitrones; C063449:zileuton; D006918:Hydroxyurea