120331-52-4Relevant academic research and scientific papers
HETEROCYCLES FROM CARBOHYDRATE PRECURSORS. ISOMERISM AND REACTIONS OF SOME ARYLHYDRAZONES OF DEHYDRO-L-ASCORBIC ACID AND ITS D-erythro AND D-arabino ANALOGUES
Kilany, Yeldez El,Mousaad, Ahmed,Hamid, Hamida Abdel,Ashry, El Sayed H. El
, p. 617 - 622 (2007/10/02)
Regioselective hydrazonation of dehydro-L-ascorbic acid and its analogues with acetone arylhydrazones gave the corresponding 2-arylhydrazones, while their direct reaction with two equivalents of the arylhydrazine gave the corresponding 2,3-bis(arylhydrazones).The bishydrazones may exist as two geometric isomers which could be isolated in some cases.The intra- and inter-molecular hydrogen bonding of the hydrazone residues with the lactone carbonyl or the solvent played a major role in their isomerisation.Their reactions and spectral data have been studied.
SYNTHESIS AND REACTIONS OF SOME HYDRAZONES OF DEHYDRO-L-ASCORBIC ACID
Kilany, Yeldez El,Hamid, Hamida Abdel,Ashry El, Sayed H. El
, p. 77 - 84 (2007/10/02)
L-threo-2,3-Hexodiulosono-1,4-lactone 2-(3-chlorophenylhydrazone) and 4-(2-acetoxyethylidene)-4-hydroxy-2,3-dioxobutano-1,4-lactone 2-(3-chlorophenylhydrazone) were prepared.The two geometric isomers of the corresponding bis(hydrazone) underwent an intramolecular rearrangement to 1-(3-chlorophenyl)-3-(L-threo-glycerol-1-yl)-4,5-pyrazoledione 4-(3-chlorophenylhydrazone), which gave a tri-O-acetyl derivative upon acetylation and the anticipated formyl derivative upon periodate oxidation.Oxidation of the bis(hydrazone) with cupric chloride afforded the bicyclic compound 3,6-anhydro-3-C-(3-chlorophenylazo)-L-xylo-2-hexulosono-1,4-lactone 2-(3-chlorophenylhydrazone), whose acetylation afforded the mono-O-acetyl derivative.
