Reduction of Dehydroascorbic Acid Osazone and Related Compounds

Document Type

Article

Publication Date

11-1-1972

Abstract

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.

Publication Title

Journal of Organic Chemistry

Link to Full Text

Share

COinS