有机膦催化的联烯酯的环加成和加成反应及反应产物的生物活性研究
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摘要
有机膦化合物已经被广泛地用于合成有机化学,比较知名的如在Wittig反应、Appel反应、Staudinger反应、Mitsunobu反应、Morita-Baylis-Hillman反应、Rauhut-Currier反应等反应中的应用。在上世纪的90年代之前,有关有机膦作为亲核催化剂的研究很少,然而在过去20年有机膦催化的有机反应已经成为一个研究热点,得到了显著的发展。目前,亲核有机膦催化的环化反应已经成为高效的合成碳环和杂环化合物的方法之一,用于从简单的初始原料合成各种各样的环状化合物。
一般地说,亲核有机膦催化的联烯的环化反应起始于有机膦对活化联烯的亲核加成反应,由此产生的zwitterionic中间体和亲电试剂反应完成环状化合物的构建。在有机膦催化条件下,活化联烯展现出了对亲电试剂的超级多样的反应性,可以作为一碳、二碳、三碳和四碳合成子与多种多样的亲电试剂如醛、烯、亚胺、氮杂环丙烷反应,完成[2+1]、[4+1]、[3+2]、[2+2+2]、[3+3]、[4+2]、[4+3]或者[8+2]环化反应。联烯这种特殊的反应性一般是通过亲电偶联试剂诱导出来的,因此寻找和探索新的具有适当反应性的亲电底物用于合成具有新的骨架或者结构特征的杂环分子成为用有机膦催化合成多样性杂环分子研究中的主要挑战。在这种背景下,本论文使用偶氮次甲基亚胺作为亲电偶联试剂用于有机膦催化的联烯酯的环加成反应,成功发展了有机膦催化的联烯酯与C,N-环状偶氮次甲基亚胺的[3+2]和[4+3]环加成反应,可以高收率得到目标产物。在这个反应中,使用α-烷基取代的联烯,无论使用三丁基膦还是三甲基膦作为催化剂,都以良好到优秀的产率得到[3+2]环加成产物；使用β’-芳基联烯,使用三丁基膦,主要得到[4+3]环加成产物;使用三甲基膦,主要得到[3+2]环加成产物。论文对有机膦催化的联烯酯与N,N,-四元环状偶氮次甲基亚胺反应进行研究,通过对催化剂、溶剂等条件的筛选,发现不能发生预想的反应(见下式)。
膦催化联烯酯和5-苯基-3-吡唑啉酮(化合物6)进行反应生成取代的3-吡唑啉酮类化合物(见下式),文献调研该类化合物具有较好的生物活性。
鉴于这些四氢吡唑并环类杂环化合物一般都具有较好的生物活性,论文还开展了对所得杂环化合物的生物活性研究。经测定发现,虽然这些化合物在除草剂和杀虫剂方而没有生物活性,但是在杀菌剂方面表现出一定的生物活性,其中有2个化合物的活性高于对照药物苯醚甲环唑,可作为先导化合物开展进一步的新农药创制研究。
Phosphines are widely used as stoichiometric reagents or catalysts in organic synthesis. Their importance has been witnessed by several well-known name reactions such as the Wittig reaction for olefin formation, Staudinger reaction for formation of amines and derivatives, and Mitsunobu reaction, especially for the formation of esters. The significant potentialities of phosphines have further been exploited by applying them in the Michael, Morita-Baylis-Hillman, annulation and isomerization reactions et al. The reactions involving phosphines as reagents or catalysts can often be carried out under mild conditions, and are compatible with many different functional groups, providing a variety of useful molecules with a high degree of functionalization. Consequently, those reactions (and their enantioselective variants) have been widely applied in the synthesis of polyfunctionalized derivatives such as biologically active heterocycles and total synthesis of natural products.
Recently, developing new reactions with phosphines as reagents or catalysts has attracted great attention. Activated allenes subjected to nucleophilic phosphine catalysis conditions exhibit superbly diverse reactivity toward electrophilic reagents. These allenes can function as one-, two-, three-, or four-carbon synthons when reacting with a variety of electrophilic coupling partners (including aldehydes, alkenes, imines, and aziridines) undergoing [2+1],[4+1],[3+2],[2+2+2],[3+3],[4+2],[4+3], or [8+2] annulations. The particular reactivity of the allene substrate is often induced by its electrophilic coupling partner. Consequently, the search for new electrophilic substrates exhibiting suitable reactivity for effective use in the synthesis of heterocycles with new skeletons or structural features is a major challenge for the formation of diverse cycloaddition products from the nucleophilic phosphine catalysis of allenes. In this context, we employed azomethine imines as a new type of electrophilic coupling reagent and accomplished the phosphine-catalyzed [3+N] annulations of azomethine imines with allenoates.
In this dissertation we describe the phosphine-catalyzed [3+2], and [4+3] annulations of azomethine imines (1) and allenoates. Phosphine-catalyzed [3+2] and [4+3] annulation reactions of C,N-cyclic azomethine imines with allenoates have been developed to give a variety of pharmaceutically attractive tetrahydroisoquinoline derivatives in moderate to excellent yields. The two distinct reaction pathways,[3+2] and [4+3] cyclization, depend on the nature of nucleophilic phosphine and allenoate. Generally, for α-alkyl allenoates, the reactions always proceed with [3+2] cyclization as major pathway no matter what phosphine was used; for a-ArCH2-substittuted allenoates, the reaction pathway was controled by the phosphine catalyst used.
In order to expand the scope of azomethine imines, the reaction of azomethine imine (5) with allenoate (2f) has also been designed and tried. Various reaction conditions have been examined, but the desired reaction did not work.
In addition we describe the phosphine-catalyzed additions of5-phenylpyrazolidin-3-one (compound6) and allenoates. Some3-pyrazolone derivatives (compound7) are prepared.
Since dinitrogen-fused heterocycles often display excellent bioactivities, the bioactivities of the cycloaddition reaction have also been studied. By the bioassay, although the products haven't herbicidal and insecticidal activities, they demonstrate excellent bactericidal activities. Especially, two compounds displayed higher activities than the control pesticides. The facts demonstrate these compounds could be used as the lead compound for the further pesticide discovery.
一般地说,亲核有机膦催化的联烯的环化反应起始于有机膦对活化联烯的亲核加成反应,由此产生的zwitterionic中间体和亲电试剂反应完成环状化合物的构建。在有机膦催化条件下,活化联烯展现出了对亲电试剂的超级多样的反应性,可以作为一碳、二碳、三碳和四碳合成子与多种多样的亲电试剂如醛、烯、亚胺、氮杂环丙烷反应,完成[2+1]、[4+1]、[3+2]、[2+2+2]、[3+3]、[4+2]、[4+3]或者[8+2]环化反应。联烯这种特殊的反应性一般是通过亲电偶联试剂诱导出来的,因此寻找和探索新的具有适当反应性的亲电底物用于合成具有新的骨架或者结构特征的杂环分子成为用有机膦催化合成多样性杂环分子研究中的主要挑战。在这种背景下,本论文使用偶氮次甲基亚胺作为亲电偶联试剂用于有机膦催化的联烯酯的环加成反应,成功发展了有机膦催化的联烯酯与C,N-环状偶氮次甲基亚胺的[3+2]和[4+3]环加成反应,可以高收率得到目标产物。在这个反应中,使用α-烷基取代的联烯,无论使用三丁基膦还是三甲基膦作为催化剂,都以良好到优秀的产率得到[3+2]环加成产物；使用β’-芳基联烯,使用三丁基膦,主要得到[4+3]环加成产物;使用三甲基膦,主要得到[3+2]环加成产物。论文对有机膦催化的联烯酯与N,N,-四元环状偶氮次甲基亚胺反应进行研究,通过对催化剂、溶剂等条件的筛选,发现不能发生预想的反应(见下式)。
膦催化联烯酯和5-苯基-3-吡唑啉酮(化合物6)进行反应生成取代的3-吡唑啉酮类化合物(见下式),文献调研该类化合物具有较好的生物活性。
鉴于这些四氢吡唑并环类杂环化合物一般都具有较好的生物活性,论文还开展了对所得杂环化合物的生物活性研究。经测定发现,虽然这些化合物在除草剂和杀虫剂方而没有生物活性,但是在杀菌剂方面表现出一定的生物活性,其中有2个化合物的活性高于对照药物苯醚甲环唑,可作为先导化合物开展进一步的新农药创制研究。
Phosphines are widely used as stoichiometric reagents or catalysts in organic synthesis. Their importance has been witnessed by several well-known name reactions such as the Wittig reaction for olefin formation, Staudinger reaction for formation of amines and derivatives, and Mitsunobu reaction, especially for the formation of esters. The significant potentialities of phosphines have further been exploited by applying them in the Michael, Morita-Baylis-Hillman, annulation and isomerization reactions et al. The reactions involving phosphines as reagents or catalysts can often be carried out under mild conditions, and are compatible with many different functional groups, providing a variety of useful molecules with a high degree of functionalization. Consequently, those reactions (and their enantioselective variants) have been widely applied in the synthesis of polyfunctionalized derivatives such as biologically active heterocycles and total synthesis of natural products.
Recently, developing new reactions with phosphines as reagents or catalysts has attracted great attention. Activated allenes subjected to nucleophilic phosphine catalysis conditions exhibit superbly diverse reactivity toward electrophilic reagents. These allenes can function as one-, two-, three-, or four-carbon synthons when reacting with a variety of electrophilic coupling partners (including aldehydes, alkenes, imines, and aziridines) undergoing [2+1],[4+1],[3+2],[2+2+2],[3+3],[4+2],[4+3], or [8+2] annulations. The particular reactivity of the allene substrate is often induced by its electrophilic coupling partner. Consequently, the search for new electrophilic substrates exhibiting suitable reactivity for effective use in the synthesis of heterocycles with new skeletons or structural features is a major challenge for the formation of diverse cycloaddition products from the nucleophilic phosphine catalysis of allenes. In this context, we employed azomethine imines as a new type of electrophilic coupling reagent and accomplished the phosphine-catalyzed [3+N] annulations of azomethine imines with allenoates.
In this dissertation we describe the phosphine-catalyzed [3+2], and [4+3] annulations of azomethine imines (1) and allenoates. Phosphine-catalyzed [3+2] and [4+3] annulation reactions of C,N-cyclic azomethine imines with allenoates have been developed to give a variety of pharmaceutically attractive tetrahydroisoquinoline derivatives in moderate to excellent yields. The two distinct reaction pathways,[3+2] and [4+3] cyclization, depend on the nature of nucleophilic phosphine and allenoate. Generally, for α-alkyl allenoates, the reactions always proceed with [3+2] cyclization as major pathway no matter what phosphine was used; for a-ArCH2-substittuted allenoates, the reaction pathway was controled by the phosphine catalyst used.
In order to expand the scope of azomethine imines, the reaction of azomethine imine (5) with allenoate (2f) has also been designed and tried. Various reaction conditions have been examined, but the desired reaction did not work.
In addition we describe the phosphine-catalyzed additions of5-phenylpyrazolidin-3-one (compound6) and allenoates. Some3-pyrazolone derivatives (compound7) are prepared.
Since dinitrogen-fused heterocycles often display excellent bioactivities, the bioactivities of the cycloaddition reaction have also been studied. By the bioassay, although the products haven't herbicidal and insecticidal activities, they demonstrate excellent bactericidal activities. Especially, two compounds displayed higher activities than the control pesticides. The facts demonstrate these compounds could be used as the lead compound for the further pesticide discovery.
引文
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