芳基三氮烯类化合物在有机合成中的应用
摘要
芳基三氮烯是一类多样化的有机化合物,它广泛应用于组合化学、配位化学、聚合物的合成、杂环化合物的合成以及医药化学等方面。它的生物活性来自于它可以形成对DNA进行烷基化的重氮盐。此外,三氮烯还可以转化为各种不同的官能团。例如：碘甲烷诱导下的芳基三氮烯可以转化为碘苯,而碘苯又可以广泛的应用于偶联反应中。芳基三氮烯可以看做芳基重氮盐的前驱体,它制备简单,易于保存,对各种官能团都有较好的兼容性。本论文报道了以芳基三氮烯为底物,合成了一系列杂环类化合物的研究。论文主要分为四部分：
1.三氟化硼乙醚促进下,我们以芳基三氮烯类化合物为底物,以中等到优秀的收率制备了一系列二苯并吡喃酮类衍生物。该反应条件温和,不需要金属催化,并对各种不同取代基的官能团都有较好的容忍性。此外,此方法还成功的应用到香豆素和菲啶酮类化合物的合成中。
2.三氟化硼乙醚促进条件下,我们建立了一种简单有效的方式来合成二苯并噻吩类的化合物。反应在无金属的温和条件下进行,并且对不同的官能团都有比较好的容忍性。我们推测反应机理是通过芳基正离子的形式进行,甲硫基作为亲核试剂发生分子内的关环反应。
3.我们建立了一种铜催化的2-卤代芳基三氮烯和叠氮化钠在水相里的串联反应。该反应具有高度的区域选择性,一系列2-芳基和2-胺基苯并三氮唑都可以以中等到优秀的产率获得。该反应步骤简单,起始物和催化剂易得,为从芳基三氮烯和芳基偶氮化合物区域选择性的合成2H-苯并三氮唑类化合物提供了一种简单实用的方法。
4.我们发展了一种银促进下2H-咪唑盐肉桂酸酯发生分子内的关环反应来合成咪唑并吲哚类的化合物。产物在水相中以中等到优秀的产率获得。到目前为止,吲哚并咪唑类的化合物研究的还比较少。该方法为合成此类稠环类的化合物提供了一种可靠的方法。
Triazenes are very useful and diverse class of compounds. They have been studied for their anticancer potential, used as protecting groups in natural product synthesis and combinatorial chemistry, incorporated into polymer and oligomer synthesis, and used to form novel heterocycles. Their biological activity derives from their ability to form diazonium salts that can alkylate DNA. Triazenes can also be transformed into several different reactive groups after treating with the appropriate reagents. Disubstituted triazenes can also form anions that are useful as ligands in organometallic chemistry. Triazenes are easily synthesized from readily available anilines or alkyl azides. Duing the past years, I have synthesized a series of organic compounds including dibenzothiophenes, dibenzopyranones, benzotriazoles. My major work is listed as follows:
1. We have developed an efficient method for the lactonization of thiazene esters promoted by BF3·OEt2. This approach works well to form various dibenzopyranones with moderate to excellent yield under mild and transition metal-free conditions. Moreover, the approach has been successfully applied to form coumarins and phenanthridinones.
2. The annulation of aryl triazenes promoted by BF3·OEt2has been demonstrated. A series of dibenzothiophenes can be formed in moderate to excellent yield and various functional groups can be tolerated under the mild and metal-free conditions. We propose that the reaction is through aryl cation intermediate and methylthio groups are reacted as the nucleophile.
3. A copper-catalyzed cascade reaction of2-haloaryltriazenes and sodium azide in water is described. The reaction is highly regioselective and a number of2-aryl or2-aminobenzotriazoles have been obtained in moderate to excellent yields. The procedure is simple and the starting materials and the catalyst are easily available. This offers a practical and convenient synthetic route to2-substituted benzotriazoles from aryltriazenes and azo compounds.
4. We have developed silver-assisted intramolecular cyclization of 2-imidazoliumylcinnamic esters selectively form1H-imidazo[1,2-α]indole derivatives in good to excellent yields. The reaction was performed in water and the starting materials are easily available. So far the synthesis and uses of imidazo[1,2-a]indoles has remained undeveloped. The present reaction offers a reliable synthetic approach of the fused heterocyclic compounds.
1.三氟化硼乙醚促进下,我们以芳基三氮烯类化合物为底物,以中等到优秀的收率制备了一系列二苯并吡喃酮类衍生物。该反应条件温和,不需要金属催化,并对各种不同取代基的官能团都有较好的容忍性。此外,此方法还成功的应用到香豆素和菲啶酮类化合物的合成中。
2.三氟化硼乙醚促进条件下,我们建立了一种简单有效的方式来合成二苯并噻吩类的化合物。反应在无金属的温和条件下进行,并且对不同的官能团都有比较好的容忍性。我们推测反应机理是通过芳基正离子的形式进行,甲硫基作为亲核试剂发生分子内的关环反应。
3.我们建立了一种铜催化的2-卤代芳基三氮烯和叠氮化钠在水相里的串联反应。该反应具有高度的区域选择性,一系列2-芳基和2-胺基苯并三氮唑都可以以中等到优秀的产率获得。该反应步骤简单,起始物和催化剂易得,为从芳基三氮烯和芳基偶氮化合物区域选择性的合成2H-苯并三氮唑类化合物提供了一种简单实用的方法。
4.我们发展了一种银促进下2H-咪唑盐肉桂酸酯发生分子内的关环反应来合成咪唑并吲哚类的化合物。产物在水相中以中等到优秀的产率获得。到目前为止,吲哚并咪唑类的化合物研究的还比较少。该方法为合成此类稠环类的化合物提供了一种可靠的方法。
Triazenes are very useful and diverse class of compounds. They have been studied for their anticancer potential, used as protecting groups in natural product synthesis and combinatorial chemistry, incorporated into polymer and oligomer synthesis, and used to form novel heterocycles. Their biological activity derives from their ability to form diazonium salts that can alkylate DNA. Triazenes can also be transformed into several different reactive groups after treating with the appropriate reagents. Disubstituted triazenes can also form anions that are useful as ligands in organometallic chemistry. Triazenes are easily synthesized from readily available anilines or alkyl azides. Duing the past years, I have synthesized a series of organic compounds including dibenzothiophenes, dibenzopyranones, benzotriazoles. My major work is listed as follows:
1. We have developed an efficient method for the lactonization of thiazene esters promoted by BF3·OEt2. This approach works well to form various dibenzopyranones with moderate to excellent yield under mild and transition metal-free conditions. Moreover, the approach has been successfully applied to form coumarins and phenanthridinones.
2. The annulation of aryl triazenes promoted by BF3·OEt2has been demonstrated. A series of dibenzothiophenes can be formed in moderate to excellent yield and various functional groups can be tolerated under the mild and metal-free conditions. We propose that the reaction is through aryl cation intermediate and methylthio groups are reacted as the nucleophile.
3. A copper-catalyzed cascade reaction of2-haloaryltriazenes and sodium azide in water is described. The reaction is highly regioselective and a number of2-aryl or2-aminobenzotriazoles have been obtained in moderate to excellent yields. The procedure is simple and the starting materials and the catalyst are easily available. This offers a practical and convenient synthetic route to2-substituted benzotriazoles from aryltriazenes and azo compounds.
4. We have developed silver-assisted intramolecular cyclization of 2-imidazoliumylcinnamic esters selectively form1H-imidazo[1,2-α]indole derivatives in good to excellent yields. The reaction was performed in water and the starting materials are easily available. So far the synthesis and uses of imidazo[1,2-a]indoles has remained undeveloped. The present reaction offers a reliable synthetic approach of the fused heterocyclic compounds.
引文
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