Title

Reactions of the 3-oxime 2-phenylhydrazone and mixed bishydrazones of dehydro-L-ascorbic acid: Conversion into substituted triazoles and pyrazolinediones

Document Type

Article

Publication Date

1-1-1977

Abstract

L-threo-2,3-Hexodiulosono-1,4-lactone 2-phenylhydrazone (1) reacted with hydroxylamine to give the 3-oxime 2-phenylhydrazone (2). On boiling with acetic anhydride, 2 was dehydrated to 4-[L-threo-2,3-diacetoxy-(1-hydroxypropyl)]-2-phenyl-1,2,3-triazole-5-carboxylic acid lactone (3), which was converted into 2-phenyl-4-(L-threo-1,2,3-trihydroxypropyl)-1,2,3-triazole-5-carboxamide (4) with liquid ammonia. The structure of compound 4 was confirmed by acetylation to 2-phenyl-4-(L-threo-1,2,3-triacetoxypropyl)-1,2,3-triazole-5-carboxamide (5), and by periodate oxidation followed by reduction, to give 4-(hydroxymethyl)-2-phenyl-1,2,3-triazole-5-carboxamide (6). Treatment of compound 1 with aryl- or aroyl-hydrazines afforded mixed bishydrazones (7-14), which were acetylated to 15-21, and treated with hydrazine to give pyrazolinediones 22 and 23. © 1977.

Publication Title

Carbohydrate Research

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