Metabolic and photochemical hydroxylation of 5-nitro-2-furancarboxaldehyde derivatives

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Abstract
The potassium of salt of 1-[[(5-aci-nitro-4,5-dihydro-4-oxo-2-furanyl)methylene]amino]-2,4-imidazolidinedione was isolated from the urine of rats fed nitrofurantoin. An aldehyde absorbing at 400 nm was synthesized photochemically in less than 1% yield from 5-nitro-2-furancarboxaldehyde diacetate (1) and the hydroxylamine, 3-amino-2-oxazolidinone and 1-amino-2,4-imidazolidinedione derivatives were prepared. On the basis or IR and NMR data,4 compounds are considered derivatives of 4-hydroxy-5-nitro-2-furancarboxaldehyde which are mainly in the aci-nitro form. Methyl and ethyl nitronic esters were synthesized. The photochemical hydroxylation of 1 also yields 3,4-dihydroxy-5-nitro-2-furancarboxaldehyde, isolated as 3-[[(3,4-dimethoxy-5-nitro-2-furanyl)-methylene]amino]-2-oxazolidinone.

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