Reduction of Dehydroascorbic Acid Osazone and Related Compounds
Reduction of dehydro-L-ascorbic acid phenylosazone (1) with LiAlH4 resulted in the hydrogenation of the hydrazone residues and cyclization to a bicyclic compound 2, which was dehydrated during acétylation with boiling Ac2O to give diacetate 3, and then partially hydrolyzed to monoacetate 4. Reduction of the L-threo and D-erythro derivatives of 1-phenyl-3-trihydroxypropyl-4,5-pyrazoledione-4-phenylhydrazone (5) with Zn in AcOH afforded the bis(L-threo- and -(D-erythro-trihydroxypropyl)rubiazonic acid analogs 6, which could be converted to the starting pyrazoles by treatment with phenylhydrazine, or oxidized with periodate to the formylrubiazonic acid. © 1972, American Chemical Society. All rights reserved.
Journal of Organic Chemistry
El Khadem, H.,
El Sekeili, M.
Reduction of Dehydroascorbic Acid Osazone and Related Compounds.
Journal of Organic Chemistry,
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