ACID-CATALYZED ADDITION OF N-HYDROXYUREA TO 1-ARYL ALCOHOL DERIVATIVES: A NEW SYNTHESIS OF ZILEUTON

Abstract

A highly efficient synthesis of Zileuton is described in which the key step involves a site-specific alkylation of hydroxyurea under acid catalysis. Various aryl alcohol electrophiles were tested and the reaction was found to be highly substrate-specific, favoring benzothiophene and benzofuran-based alcohols.

Keywords:

• Alkylation
• Hydroxamic Acids and Derivatives
• Regioselection

ACKNOWLEDGMENT

The authors wish to thank Professor H. Rapoport for helpful discussions.