2H-氮杂丙烯啶衍生物的合成及重排反应的新方法研究
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摘要
2H-氮杂丙烯啶是自然界中最小的不饱和氮杂三元环分子,它具有很强的环张力,是一类非常活泼的有机中间体。由于其在自然界中的广泛存在以及在氨基衍生物和含氮杂环构建过程中的巨大潜力,化学家对这类分子进行了深入地研究。这篇论文研究的重点是氮杂丙烯啶衍生物的合成及其在加热条件下的重排反应,主要包含以下几个方面:
1.为了研究此方法的适应范围,本文通过含不同取代基的酮类与甲酸铵的缩合反应合成了一系列烯胺类底物。
2.在高价有机碘氧化剂—二乙酰氧碘苯(PIDA)的作用下,2-芳基腈酮类底物可以按照此方法高产率的转化为相应的2-芳基-2-腈基-2H-氮杂丙烯啶类化合物。另外,底物中的腈基可以被其它吸电子基团取代,例如,乙酰基或者酯基。让我们高兴的是,当E基团是乙酰基时,烯胺类底物可以在同样的反应条件下高产率的转化为相应的2H-氮杂丙烯啶类化合物,同时,不管苯环上含有的是供电子基团还是吸电子基团,此反应都可以进行地非常顺利。然而,当E基团是乙酯基的时候,只有少数几个例子可以实现这种转化。当苯环上含有的是H或者供电子基团时,实验过程中未观察到2H-氮杂丙烯啶类化合物的生成。
3.所获得的2-芳基-2H-氮杂丙烯啶类化合物可以在加热条件下高产率的转化为3位官能团化的吲哚环化合物,其中E基团必须是腈基或者酯基。
4.当E基团是乙酰基的时候,所获得的2-芳基-2H-氮杂丙烯啶类化合物在加热的条件下通过分子内环合生成了异噁唑类衍生物,而在实验过程中未发现吲哚类化合物的生成。
2H-Azirines, a class of highly strained and reactive molecules with a C=N bond incorporated into a three-membered ring, have been extensively studied for their presence in natural products and high synthetic potential in the synthesis of functionalized aminoderivatives and N-containing heterocycles. This paper focuses on the synthetic methodology of 2H-azirines derivatives and their rearrangements under thermal conditions. It covers the following aspects:
1. In order to study the scope and generality of this method, different substituted enamine substrates were synthesized by condensation of the substituted ketones with ammonium formate.
2. Mediated by phenyliodine (III) diacetate (PIDA), a variety of enamines fromα-aryl ketonitriles with different substitution patterns could be applied to this methodology, and the corresponding 2-aryl-2H-azirine-2-carbonitriles were achieved in pleasant yields. In addition, the cyano group in such substrates could be replaced by other electron-withdrawing groups, e.g., a carbonyl moiety or an ethoxycarbonyl group. To ourdelight, the enamines of 3-arylacetylacetones also afforded the corresponding 2H-azirines in desirable yields under the same reaction conditions, and both electron-withdrawing and electron-donating aromatic substituents were well tolerated. However, when the electron-withdrawing group was an ethoxycarbonyl group, the desired azirine products could be achieved in few examples. When the nitro group was replaced by H or methoxy substituents on the benzene ring, no desired azirine products were obtained under the same reaction condition.
3. The obtained 2-aryl-2H-azirines derivatives could be transformed to their corresponding 3-functionalized indole compounds under thermal conditions, in which E represents a cyano or an ethoxycarbonyl group.
4. When E was an acetyl group, the azirine substrates underwent an intramolecuar O-N formation to afford isoxazole derivatives in pleasant yields under thermal conditions. In addition, no desired indole compounds were detected during this transformation process.
1.为了研究此方法的适应范围,本文通过含不同取代基的酮类与甲酸铵的缩合反应合成了一系列烯胺类底物。
2.在高价有机碘氧化剂—二乙酰氧碘苯(PIDA)的作用下,2-芳基腈酮类底物可以按照此方法高产率的转化为相应的2-芳基-2-腈基-2H-氮杂丙烯啶类化合物。另外,底物中的腈基可以被其它吸电子基团取代,例如,乙酰基或者酯基。让我们高兴的是,当E基团是乙酰基时,烯胺类底物可以在同样的反应条件下高产率的转化为相应的2H-氮杂丙烯啶类化合物,同时,不管苯环上含有的是供电子基团还是吸电子基团,此反应都可以进行地非常顺利。然而,当E基团是乙酯基的时候,只有少数几个例子可以实现这种转化。当苯环上含有的是H或者供电子基团时,实验过程中未观察到2H-氮杂丙烯啶类化合物的生成。
3.所获得的2-芳基-2H-氮杂丙烯啶类化合物可以在加热条件下高产率的转化为3位官能团化的吲哚环化合物,其中E基团必须是腈基或者酯基。
4.当E基团是乙酰基的时候,所获得的2-芳基-2H-氮杂丙烯啶类化合物在加热的条件下通过分子内环合生成了异噁唑类衍生物,而在实验过程中未发现吲哚类化合物的生成。
2H-Azirines, a class of highly strained and reactive molecules with a C=N bond incorporated into a three-membered ring, have been extensively studied for their presence in natural products and high synthetic potential in the synthesis of functionalized aminoderivatives and N-containing heterocycles. This paper focuses on the synthetic methodology of 2H-azirines derivatives and their rearrangements under thermal conditions. It covers the following aspects:
1. In order to study the scope and generality of this method, different substituted enamine substrates were synthesized by condensation of the substituted ketones with ammonium formate.
2. Mediated by phenyliodine (III) diacetate (PIDA), a variety of enamines fromα-aryl ketonitriles with different substitution patterns could be applied to this methodology, and the corresponding 2-aryl-2H-azirine-2-carbonitriles were achieved in pleasant yields. In addition, the cyano group in such substrates could be replaced by other electron-withdrawing groups, e.g., a carbonyl moiety or an ethoxycarbonyl group. To ourdelight, the enamines of 3-arylacetylacetones also afforded the corresponding 2H-azirines in desirable yields under the same reaction conditions, and both electron-withdrawing and electron-donating aromatic substituents were well tolerated. However, when the electron-withdrawing group was an ethoxycarbonyl group, the desired azirine products could be achieved in few examples. When the nitro group was replaced by H or methoxy substituents on the benzene ring, no desired azirine products were obtained under the same reaction condition.
3. The obtained 2-aryl-2H-azirines derivatives could be transformed to their corresponding 3-functionalized indole compounds under thermal conditions, in which E represents a cyano or an ethoxycarbonyl group.
4. When E was an acetyl group, the azirine substrates underwent an intramolecuar O-N formation to afford isoxazole derivatives in pleasant yields under thermal conditions. In addition, no desired indole compounds were detected during this transformation process.
引文
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