Abstract
This paper presents the successful implementation of Beckmann rearrangement on a series of (spiro)pyranocoumarin oximes in polyphosphoric acid (PPA) medium. The method demonstrated excellent proficiency in the synthesis of unexpected imines as major products and amides as minor products. The labeled 15NH2OH·HCl control experiment yielded oxime and rearrangement products that incorporated the 15N label. Furthermore, we have proposed a possible rearrangement mechanism. NMR spectroscopy data (correlation HMBC and 15N NMR) confirmed the structure of the synthesized products. These findings provide a new and efficient approach for constructing complex imines with diverse applications in synthetic organic chemistry.
Published Version
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