Regioselective Beckmann rearrangements of furanoside and pyranoside-derived oximes |
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Authors: | Rajdeep K BenningHelen MI Osborn Andrea Turkson |
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Institution: | a Department of Chemistry, University of Reading, Whiteknights, Reading RG6 6AD, United Kingdom b Reading School of Pharmacy, University of Reading, Whiteknights, Reading RG6 6AD, United Kingdom |
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Abstract: | The Beckmann rearrangement is a useful reaction employed to provide access to amides from oxime substrates. Applied to cyclic structures, the Beckmann rearrangement leads to ring expansion and allows access to cyclic lactams. Our investigations focused upon the synthesis of glycoside-derived lactams from oxime precursors. In probing a range of conditions, we observed that 2,4,6-trichloro1,3,5]triazine (TCT) was an effective and mild promoter of the rearrangement affording pyrano- and heptanoside lactam products with excellent regioselectivities. |
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