3-脱氢莽草酸甲酯与肼类化合物反应的选择性

Selective Derivation of(-)-Methyl-3-dehydroshikimate with Hydrazine Compounds

以可再生生物质资源莽草酸为原料,在经酯化和2-碘酰基苯甲酸(IBX)氧化制得3-脱氢莽草酸甲酯的基础上,研究了在不同反应溶剂中和不同反应温度下,3-脱氢莽草酸甲酯分别与水合肼、乙酰肼、苯肼和乙酰胺选择性地得到非芳构化、部分芳构化和芳构化产物的反应.该方法具有选择性高、操作简单和条件温和等优点,为可再生非粮生物质资源莽草酸的利用提供了一种新的思路.

The purpose of this paper is to achieve the high value-added and diversified transformation of the renewable biomass （-）-shikimic acid, starting from which, the key intermediate （-）-methyl-3-dehydro- shikimiate was readily obtained through esterification and 2-iodoxybenzoic acid-oxidation. The reaction of （-）-methyl-3-dehydroshikimiate with hydrazine, acethydrazide, hydrazinobenzene and acetamide could give rise to non-aromatization products （2a and 2d）, partial-aromatization products （2b） and aromatization products （2c and 2e） selectively under different conditions. The present methodology with good diversity, high selec- tivity and operational simplicity provides a new paradigm for the transformation of bio-based and non-food feed- stock.