HYDROGENATION PRODUCTS FROM DEHYDRO-DERYTHRO-AND DEHYDRO-L-THREO-ASCORBICACIDS MONO- AND BISHYDRAZONES

Reaction of dehydro-D-isoascorbic acid with benzoylhydrazine gave thebisbenzoylhydrazone which, upon hydrogenation in the presence of Pd/C catalyst,gave thc 2,3-diamino-2,3-dideoxy-D-isoascorbic acid. Reaction of the lattercompound with different aldehydes afforded, the bicyclic imidazoline derivatives,and with arylglyoxal, gave the bicyclic pyrazine derivaties. The 2,3-diamino-2,3-dideoxy-L-ascorbic acid reacted with anhyrous HCOOH giving the monoformylderivativeand with glyoxal to give a bicyclic pyrazine derivative. NaBH 4 reductionof dehydro-L-ascorbic acid-2-p-chlorophenylhy drazone, gave the bicydic 3,6-anhydro-derivative which was hydrogenated in the presence of Pd/C to give the 2-amino-2-deoxy derivative.