Iodine-mediated new strategy for the synthesis of 2,5-disubstituted oxazoles from methyl ketones and TosMIC

Abstract

A new strategy has been developed for the construction of oxazoles from methyl ketones and TosMIC via self-sorting oxidative domino reaction strategy. In contrast to its usual reactivity as C–N≡C synthon in the synthesis of oxazoles, TosMIC was utilized as ammonium surrogate in the present method. The protocol is attractive in terms of readily available starting materials, metal and base free conditions, operational simplicity, C–N and C–O bond formation. A variety of 2,5-disubstituted oxazoles were prepared in moderate-to-good yields.

Graphical Abstract

Keywords:

• 2,5-Disubstituted oxazoles
• metal and base free conditions
• methyl ketones
• self-sorting oxidative domino reaction
• TosMIC

Acknowledgments

Y.Lakshmi Prapurna thanks Department of Science and Technology (DST) for financial grant under Women Scientists Scheme-A (WOS-A), Grant No. SR/WOS-A/CS-1034/2014 (G). N.P. acknowledges UGC, New Delhi for fellowship support.

Additional information

Funding

This work was financially supported by the Department of Science and Technology (DST) for financial grant under Women Scientists Scheme-A (WOS-A), [Grant No. SR/WOS-A/CS-1034/2014 (G)] and UGC, New Delhi for fellowship support.