A facile method for regioselective synthesis of new N-acetyl/thioacetyl-(E)-stilbene benzenesulfonamide derivatives via N-acetyl/thioacetyl sulfonamide formation

GRAPHICAL ABSTRACT

ABSTRACT

A series of new N-acetyl/thioacetyl-(E)-stilbene benzenesulfonamide derivatives were synthesized regioselectively in moderate to high yields by following a convenient, three-step procedure. The procedure consists of the direct oxidative conversion of a thiol compound to the corresponding sulfonyl chloride using TMSCl/KNO₃, followed by a room temperature reaction in a one-pot transformation of the resultant sulfonyl chloride into N-acetyl/thioacetyl sulfonamide, which undergoes a further Pd-catalyzed coupling reaction, giving rise to the stilbene compounds reported for the first time.

KEYWORDS:

• Acetyl/thioacetyl sulfonamides
• COX-2 inhibitors
• N-acetyl/thioacetyl-(E)-stilbene benzenesulfonamide
• one-pot transformation

Acknowledgments

The authors wish to express their special thanks to Professor Per-Ola Norrby from University of Gothenburg. A part of this work was connected to the Pharm.D theses of M. Ahmadian and M. Tatar from Faculty of Pharmacy, Mazandaran University of Medical Sciences.

Funding

The authors gratefully acknowledge the financial support for this work received from the Mazandaran University of Medical Sciences “Professor's Projects and Sabbatical Funds.”