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首页> 外文期刊>Journal of the Indian Chemical Society >Reactions of arylhydrazones of dehydro-L-ascorbic acid and of D-arabino-2,3-diulosono-i,4-lactone
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Reactions of arylhydrazones of dehydro-L-ascorbic acid and of D-arabino-2,3-diulosono-i,4-lactone

机译：脱氢-L-抗坏血酸的芳基hydr与D-阿拉伯糖-2,3-二磺基-i，4-内酯的反应

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摘要

Reaction of D-arabino-2,3-heptodiulosono-1,4-lactonc with p-chlorophenylhydrazine gave the bishydrazone 2 characterized as its acetate 3 and rearranged by treatment with hydrazine hydrate, followed by acidification to pyrazolinedione 5 characterized also by its acetate 6. Cupric chloride oxidation of the bis(p-bromophenylhydrazone) 4, gave the 3,6-anhydro derivative 7 which afforded the di-O-acetyl derivative 8. p-Tolucnesulfonation of 3,6-anhydro-2-oxo-3-phenylazo-D-glucoheptono-1,4-lactone-2-phenylhydrazone (9), afforded the monotosyl derivative 10. Compound 1 reacted with acetylphenylhydrazine giving the mono (phenylhydrazone) 11 which was converted into an olefinic derivative 13 upon acetylation. L-Threo-2,3-hexodiulosono-1,4-lactone-2-(p-chlorophenylhydrazone) 14, when reacted with HBr/ AcOH, did not give the expected 6-bromo-6-deoxy derivative 15, but instead, the 5,6-dibroino-5,6-dideoxy derivative 16 is obtained, that gave a number of condensation products 17-20. Similarly, D-erythro-2,3-hexodiulosono-1,4-lactone-2-(phenylhydrazone) 21 reacted with thiosemicarbazide furnishing the 2-(phenylhydrazone)-3-thiosemicarbazone 22 characterized by its acetate 23 and rearranged to a pyrazole derivatives 24 and 25.
机译：D-阿拉伯糖-2,3-庚二酮-1,4-内酯与对氯苯肼的反应生成双hydr 2，其为醋酸盐3，并通过水合肼处理进行重排，然后酸化为吡line啉二酮5，其也为醋酸盐6 ·双（对-溴苯基hydr）4的氯化铜氧化，得到3，6-脱水衍生物7，得到二-O-乙酰基衍生物8。3，6-脱水-2-氧-3-的对甲苯磺酰化。苯基偶氮-D-葡萄糖庚基-1，4-内酯-2-苯基hydr（9），得到单甲苯磺酰基衍生物10。化合物1与乙酰基苯基肼反应，得到单（苯基hydr）11，其在乙酰化后转化为烯烃衍生物13。 L-Threo-2,3-hexodiulosono-1,4-lactone-2-（p-chlorophenylhydrazone）14与HBr / AcOH反应时，未得到预期的6-溴-6-脱氧衍生物15，而是得到5，6-二溴-5，6-二脱氧衍生物16，得到许多缩合产物17-20。类似地，D-赤型-2,3-己二磺酰基-1,4-内酯-2-（苯基hydr）21与硫代氨基脲反应，得到2-（苯基hydr）-3-硫代氨基脲22，其特征在于其乙酸盐23并且重排为吡唑衍生物。 24和25。

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