A Versatile Water-Stable Fluorine Containing Organometallic Lewis Acid Used in Green Synthesis of 1,3-Oxazine Scaffolds at Room Temperature

Abstract

A simple, straightforward, and highly efficient one-pot multicomponent synthesis of pharmaceutically interesting [1,3]-oxazine derivatives has been developed using iron(III) trifluroacetate ([Fe(CF₃CO₂)₃]) as Lewis acid in an aqueous sodium dodecyl sulfate (SDS) micellar medium. The salient features of the present protocol are mild reaction conditions, use of aqueous SDS micellar medium, good yields, eco-friendly standards, easy isolation of products, no column chromatographic separation and reusability of catalytic system. The synthesized some chromeno[1,3]oxazine derivatives were tested for their antioxidant activity using free radicals DPPH method. The screened compounds showed moderate to good activity on comparison with ascorbic acid.

Graphical Abstract

Keywords:

• Antioxidant activity
• aq. SDS micellar medium
• chromeno[1,3]oxazines
• Iron(III)trifluroacetate
• naphtho[1,3]oxazines

Acknowledgments

One of the author, Mr. Trushant Lohar is very much thankful to the Department of Science and Technology (DST) for providing DST-INSPIRE fellowship (IF-140918).

Disclosure statement

No potential conflict of interest was reported by the authors.

Scheme 1. Synthesis of naphtho[1, 3]oxazine.