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A variety of 2-substituted-2,3-dihydro-1,4 dioxino[2,3-b]pyridines B have b
een synthesized from the readily available 2-nitro-3-oxiranylmethoxypyridin
e 1 via a Smiles rearrangement. We demonstrate how variations of reaction c
onditions affect the product distribution of A and B.