Some studies on dehydro-L-ascorbic acid hydrazone : conversion into substituted triazoles and pyrazolinediones

Abstract EN

Boiling of the 2-p-nitrophenylhydrazone of dehydro-L-ascorbic acid with acetic anhydride caused the formation of an olefinic derivative that afforded the bishydrazone which rearranged to a pyrazole derivative.

The olefinic derivative gave the hydrazone oxime, that gave the triazole derivative.

Treatment of the latter with methanolic ammonia, gave the triazole carboxamide; which was characterized as its acetate.

Similar treatment of the olefinic derivative with semicarbazide, gave the hydrazone semicarbazone, which was rearranged to a pyrazole derivative upon boiling with concentrated ammonia, that in turn gave a triacetyl derivative upon acetylation.