Unexpected but prominent imines formation in Beckmann rearrangement of (spiro)pyranocoumarin oximes
Tetrahedron Letters, ISSN: 0040-4039, Vol: 129, Page: 154747
2023
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Article Description
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 15 NH 2 OH·HCl control experiment yielded oxime and rearrangement products that incorporated the 15 N label. Furthermore, we have proposed a possible rearrangement mechanism. NMR spectroscopy data (correlation HMBC and 15 N 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.
Bibliographic Details
http://www.sciencedirect.com/science/article/pii/S0040403923004574; http://dx.doi.org/10.1016/j.tetlet.2023.154747; http://www.scopus.com/inward/record.url?partnerID=HzOxMe3b&scp=85171153913&origin=inward; https://linkinghub.elsevier.com/retrieve/pii/S0040403923004574; https://dx.doi.org/10.1016/j.tetlet.2023.154747
Elsevier BV
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