基于2-磺酰亚胺基氧杂环丁烷为中间体的若干多组分反应研究
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摘要
多组分反应由于具有连续、高效,操作简便,反应收率高等优点,近年受到了有机合成界的普遍重视和广泛关注;其中,铜催化的多组分反应研究尤为引人注目。本文首先概括了CuI催化的多组分反应研究进展以及2-亚胺基氧杂环丁烷研究进展；在此基础上,我们报道了三个基于2-磺酰亚胺基氧杂环丁烷中间体的串联反应,合成了一系列结构多样性的化合物。主要内容包括：
1.我们发展了一种CuI催化的端炔、磺酰叠氮和共轭炔醛的三组分反应,在温和条件下制备了一系列多取代共轭烯炔和烯二炔。研究发现：炔醛的羰基能和原位生成的N-磺酰基烯酮亚胺发生形式[2+2]环加成反应,生成2-亚胺基氧杂环丁烷衍生物；该中间体不稳定,开环、质子化后得到官能化共轭烯炔类化合物。这个反应适用范围较广,为共轭烯炔的立体选择性合成提供了一个很有前景的方法。在此基础上,对所得烯二炔衍生物在有机合成中的应用进行了探索,研究了该类烯二炔产物的环合反应,合成了一类稠杂环化合物。
2.我们研究了CuI催化的端炔、磺酰叠氮、N-取代靛红的三组分反应,方便高效的得到了一系列的3-烯基2-氧代吲哚化合物。研究发现N-取代靛红的羰基能和原位生成的N-磺酰基烯酮亚胺发生[2+2]环加成反应,生成2-亚胺基氧杂环丁烷衍生物,该2-亚胺基氧杂环丁烷衍生物不稳定,在碱条件下开环,再通过质子化过程得到3-烯基2-氧代吲哚化合物化合物。我们还研究了非碱性条件下,产物在Au-催化下的环合反应,利用酰胺官能团的O-亲核进攻碳碳三键,得到二氢呋喃衍生物的反应。
3.我们研究了CuI催化的端炔、磺酰叠氮、N-取代靛红、水的四组分反应。该反应利用2-亚胺基氧杂环丁烷的不稳定性,用水使其开环,合成了一系列的3-墩代-3-羟基吲哚-2-酮化合物。产物结构中具有两个手性中心,其非对映异构体比例通过1HNMR确定。最后,通过H2180同位素标记,对反应机理进行探索。
Over the past decade, multicomponent reactions (MCRs) have attracted increasing attention due to the virtue of their convergence, productivity, ease of execution and generally high yields of products. In this context, copper(I)-catalyzed multicomponent reaction has been rapidly developed and achieves significant progresses. In this thesis, recent development of copper(I)-catalyzed MCRs and2-iminooxetane chemistry is initially reviewd. On this basis, we present three unprecedented MCRs via2-sulfonyl-iminooxetane intermediates. The major content involves:
1. Beneficiated by the accessible ynamido-metal intermediates from a CuI-catalyzed azide-alkyne cycloaddition in the presence of stoichiometric amounts of LiOH, a mild and flexible three-component route to conjugated enyne and endiyne scaffolds from terminal alkynes, sulfonyl azides, and ynals was successfully achieved via a formal E-selective olefination strategy. A plausible mechanism for this approach has aso been proposed. In addition, we had explored the cyclization of the resulted enediynes upon treatment with Pd" in order to demonstrate their synthestic application.
2.3-Alkenyl-oxindoles were synthesized via a copper(I)-catalyzed three-compent reaction of terminal alkynes, sulfonyl azides, and N-substituted isatins. A plausible mechanism for this approach has been proposed either. Moreover, we have explored the ring-closure reaction of the product via O-nucleophilic attacking onto the tethered C-C triple bond in the absence of base, giving rise to dihydrofuran derivatives.
3. We have developed a distinct copper(I)-catalyzed four-component reaction of terminal alkynes, sulfonyl azides, N-substituted isatins, and H2O for the synthesis of3-substituted-3-hydroxyindolin-2-ones. Upon a control experiment with H2O18as the substrate, a plausible mechanism was proposed. Two comtigous chiral carbons was generated in this process, and the diasteromeric ratio was determined by1H NMR.
1.我们发展了一种CuI催化的端炔、磺酰叠氮和共轭炔醛的三组分反应,在温和条件下制备了一系列多取代共轭烯炔和烯二炔。研究发现：炔醛的羰基能和原位生成的N-磺酰基烯酮亚胺发生形式[2+2]环加成反应,生成2-亚胺基氧杂环丁烷衍生物；该中间体不稳定,开环、质子化后得到官能化共轭烯炔类化合物。这个反应适用范围较广,为共轭烯炔的立体选择性合成提供了一个很有前景的方法。在此基础上,对所得烯二炔衍生物在有机合成中的应用进行了探索,研究了该类烯二炔产物的环合反应,合成了一类稠杂环化合物。
2.我们研究了CuI催化的端炔、磺酰叠氮、N-取代靛红的三组分反应,方便高效的得到了一系列的3-烯基2-氧代吲哚化合物。研究发现N-取代靛红的羰基能和原位生成的N-磺酰基烯酮亚胺发生[2+2]环加成反应,生成2-亚胺基氧杂环丁烷衍生物,该2-亚胺基氧杂环丁烷衍生物不稳定,在碱条件下开环,再通过质子化过程得到3-烯基2-氧代吲哚化合物化合物。我们还研究了非碱性条件下,产物在Au-催化下的环合反应,利用酰胺官能团的O-亲核进攻碳碳三键,得到二氢呋喃衍生物的反应。
3.我们研究了CuI催化的端炔、磺酰叠氮、N-取代靛红、水的四组分反应。该反应利用2-亚胺基氧杂环丁烷的不稳定性,用水使其开环,合成了一系列的3-墩代-3-羟基吲哚-2-酮化合物。产物结构中具有两个手性中心,其非对映异构体比例通过1HNMR确定。最后,通过H2180同位素标记,对反应机理进行探索。
Over the past decade, multicomponent reactions (MCRs) have attracted increasing attention due to the virtue of their convergence, productivity, ease of execution and generally high yields of products. In this context, copper(I)-catalyzed multicomponent reaction has been rapidly developed and achieves significant progresses. In this thesis, recent development of copper(I)-catalyzed MCRs and2-iminooxetane chemistry is initially reviewd. On this basis, we present three unprecedented MCRs via2-sulfonyl-iminooxetane intermediates. The major content involves:
1. Beneficiated by the accessible ynamido-metal intermediates from a CuI-catalyzed azide-alkyne cycloaddition in the presence of stoichiometric amounts of LiOH, a mild and flexible three-component route to conjugated enyne and endiyne scaffolds from terminal alkynes, sulfonyl azides, and ynals was successfully achieved via a formal E-selective olefination strategy. A plausible mechanism for this approach has aso been proposed. In addition, we had explored the cyclization of the resulted enediynes upon treatment with Pd" in order to demonstrate their synthestic application.
2.3-Alkenyl-oxindoles were synthesized via a copper(I)-catalyzed three-compent reaction of terminal alkynes, sulfonyl azides, and N-substituted isatins. A plausible mechanism for this approach has been proposed either. Moreover, we have explored the ring-closure reaction of the product via O-nucleophilic attacking onto the tethered C-C triple bond in the absence of base, giving rise to dihydrofuran derivatives.
3. We have developed a distinct copper(I)-catalyzed four-component reaction of terminal alkynes, sulfonyl azides, N-substituted isatins, and H2O for the synthesis of3-substituted-3-hydroxyindolin-2-ones. Upon a control experiment with H2O18as the substrate, a plausible mechanism was proposed. Two comtigous chiral carbons was generated in this process, and the diasteromeric ratio was determined by1H NMR.
引文
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