A convenient [hydroxy(tosyloxy)iodo]benzene-mediated one-pot synthesis of 2-arylimidazo[2,1-b]benzothiazoles

Abstract

Several 2-arylimidazo[2,1-b]benzothiazoles (4) have been conveniently synthesized in one-pot reactions via α-tosyloxylation of enolizable ketones (1) using [hydroxy(tosyloxy)iodo]benzene 2 in acetonitrile, followed by treatment with 2-amino-6-(substituted)benzothiazoles (3). The present protocol offers several advantages towards general access of 2-arylimidazo[2,1-b]benzothiazoles, including an intriguing alternative to the literature protocols, a readily available nontoxic reagent, operational simplicity and an environmentally benign procedure.

GRAPHICAL ABSTRACT

Keywords:

• α-tosyloxyketones
• [hydroxy(tosyloxy)iodo]benzene
• imidazo[2,1-b]benzothiazoles
• hypervalent iodine
• 2-amino-6-(substituted)benzothiazoles

Acknowledgements

Support to this research by authorities of D.A.V. College, Ambala City for providing laboratory facilities is gratefully acknowledged. Thanks are also due to Prof. Devinder Kumar, Department of Chemistry and Central Instrumentation Laboratory, Guru Jambheshwar University of Science & Technology, Hisar for providing NMR data.

Disclosure statement

No potential conflict of interest was reported by the authors.

Supplemental material

Supplemental data for this article can be accessed at doi:10.1080/17415993.2014.996221.