4

Filipe Correia
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引用次数: 0

摘要

我们探索了一种新的异腈,即4-(N -邻苯二胺)苯基异腈,它具有非凡的特性。这种新型异氰化物含有一个药效团,邻苯二胺(Pht)基团,具有良好的药理活性。我们发现,这种新型异腈出乎意料地无臭,这使得它在有机合成中易于处理,可以作为通过多组分反应构建几种新的酰胺衍生物的支架,克服常见芳香异腈如苯基异腈、苄基异腈、对硝基苯异腈和4-异氰基苯甲酸乙酯的臭味。新型异腈9作为带Pht基团的N保护异腈的来源,其中Pht基团可以通过肼水解去除,得到相应的伯胺/醇支架,该支架可以作为前体直接通过酰化合成Passerini产品,得到Passerini加合物14和15,而无需进行传统的Passerini三组分反应;这种新异腈被认为是一种新型的可转换异氰化物类似物。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
4
: We explored a new isonitrile, namely 4-( N -phthalimido)phenyl isonitrile, with extraordinary features. The novel isocyanide has a pharmacophore, the phthalimido (Pht) group, that possesses promising pharmaceutical activities. We found that the novel isonitrile is unexpectedly odorless as an extra bonus which makes its handling easy in organic synthesis to serve as a scaffold for building several new amide derivatives through multicomponent reactions, overcoming the stink of common aromatic isonitriles such as phenyl isonitrile, benzyl isonitrile, p -nitrophenyl isonitrile, and ethyl 4-isocyano benzoate. The novel isonitrile 9 serves as a source of N -protected isonitrile with a Pht group, where the Pht group can be easily removed via hydrazinolysis, affording the corresponding primary amine/alcohol scaffold which could be used as a precursor to synthesize Passerini products via acylation directly to afford Passerini adducts 14 and 15 without carrying out the traditional Passerini three-component reaction; this new isonitrile is considered as a novel convertible isocyanide analogue.
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