一些硒试剂在有机合成中的应用研究
摘要
多组分反应和组合化学等新型有机合成方法的出现不仅极大地加强了合成的效率,提高了经济效益,同时减少了废弃物的排放,兼顾了环境,符合可持续发展的精神。硒元素不仅是人体必需的微量元素之一,而且本身具有特殊的化学反应活性,在合成化学中被广泛使用。
本论文将有机硒试剂应用到多组分反应和组合化学中,利用它们的某些特殊反应性能,快速、高效地合成了许多在合成方面有用或者具有潜在生物活性的目标化合物。
论文主要包括两大部分：
第一部分——小分子有机硒试剂在多组分反应中的应用
1.研究了有机硒锂试剂与1-(1-炔基)环丙基酮以及亲电试剂的三组分反应。首先硒锂试剂凭借自身的亲核性进攻1-(1-炔基)环丙基酮的三元环使其开环形成一个烯醇负离子中间体,然后根据反应体系中存在的亲电试剂种类与数量不同,此中间体选择性地以其共轭的联烯负离子或者炔丙基负离子形式去进攻亲电试剂,生成(E)-4-烯-1,3二羰化合物、多取代联烯酮、多取代呋喃以及多取代含氟β,γ,-炔基酮等多种重要的有机小分子化合物。
2.发展了2-呋喃甲醛/胺/2-苯硒基丙烯酸和异腈参与的四组分反应。首先,这四个组分加到一起自发进行Ugi反应生成了β-酰胺基酰胺,此时,由于产物内恰当位置同时含有缺电子的烯烃和富电子的呋喃,在室温或者加热的条件下又会进一步发生Diels-Alder反应生成三环内酰胺化合物,通过往反应体系中加入三氟化硼乙醚,接下来依次发生的氧桥开环苯硒基消除和芳构化反应最终一锅法合成了多取代异吲哚酮类化合物。
第二部分——高分子有机硒试剂在固相有机合成中的应用
3.从聚苯乙烯负载的α-硒基-β-氨基酸酯出发,先用胺与官能团化的酸缩合,再根据酸α位官能团的不同,选择性地形成六元环或者是七元环,最后从树脂上切割下来,建立了一套固相合成2-吡啶酮,1,4-二氮杂草,和氧代1,4-二氮杂(?)化合物的方法。特别值得一提的是当使用的是手性的α-氨基酸时,其手性可以一直从原料中保持到最终的产物中,换言之就是可以使用价格低廉的天然氨基酸很便捷地合成一系列光学纯的1,4-二氮杂(?)类化合物。
4.从聚苯乙烯负载的α-硒基丙烯酸甲酯出发,先与甲亚胺叶立德发生1,3-偶极环加成反应,再经过进一步的乙内酰脲、2,5-二酮哌嗪环化反应,最后通过过氧化氢氧化消除树脂上切割下来,方便地合成了3个3-吡咯啉,3-吡咯啉并乙内酰脲和3-吡咯啉并2,5-二酮哌嗪的小分子化合物库。
The development of multi-component reactions and combinatorial chemistry enhances the efficiency of synthesis of diversified compounds, thus producing less wastes. As a result, these two new approaches have been shown with many applications in modern organic chemistry. Selenium is discovered to be an essential element for mammalian life. At the meantime, organoselenium reagents are wildly used in organic synthesis.
Based on the unique reactivities of organoselenium reagents, we have established several methods to prepare target molecules which may have potential biological or medicinal activities in a straightforward and efficient way.
This dissertation mainly includes two parts:
PartⅠ——The application of solution-phase organoselenium reagents in multi-component reactions
1. A novel three-component reaction of lithium selenolates with 1-(1-alkynyl) cyclopropyl ketones and electrophiles was developed. In this reaction, initially the lithium selenolates attack the 1-(1-alkynyl)cyclopropyl ketones to open the cyclopropane rings, then electrophiles were used to capture the formed carboanions to furnish the corresponding products. By changing the electrophiles, we can obtain (E)-4-alken-1,3-diketones,1,2-allenic ketones, furans, and fluorine substituted 1-alkynyl ketones, respectively.
2.2-Furylaldehydes, amines,2-(phenylselenyl)acrylic acids, and isocyanides were used to perform a Ugi-type four-component condensation reaction. Then at room temperature or under reflux, the corresponding products underwent a further Diels-Alder cycloaddition reaction. Promoted by BF3·OEt2, sequential oxygen bridge opening, phenylselenyl elimination, and aromatization of the Diels-Alder products finally gave the highly substituted isoindolinones.
PartⅡ——The application of resin-bound organoselenium reagents in solid-phase organic synthesis
1. The polystyrene-supported a-seleno-β-amino esters were used to react with a-functionalized acids to form the corresponding amide resins. According to the differences of functional group on the acids, six and seven-membered rings were formed respectively. After cleavage from the resins, we could prepare three libraries of 2-pyridones,1,4-diazepines, and 1,4-oxazepines. It should be noted that when natural a-amino acids were used, optically pure 1,4-diazepines would be given as the expected products.
2. The resin-bound a-seleno methyl acrylates were used to undergo 1,3-dipolar cycloaddition with azomethine ylides to furnish polystyrene-supported pyrrolidine-substituted selenide resins. Then further reactions took places on these resins to construct the hydantoin and 2,5-diketopiperazine rings. After oxidation and elimination of the selenides, the corresponding 3-pyrrolines, 3-pyrroline-fused hydantoins, and 3-pyrroline-fused 2,5-diketopiperazines were released from the resins in moderate yields and good purities.
本论文将有机硒试剂应用到多组分反应和组合化学中,利用它们的某些特殊反应性能,快速、高效地合成了许多在合成方面有用或者具有潜在生物活性的目标化合物。
论文主要包括两大部分：
第一部分——小分子有机硒试剂在多组分反应中的应用
1.研究了有机硒锂试剂与1-(1-炔基)环丙基酮以及亲电试剂的三组分反应。首先硒锂试剂凭借自身的亲核性进攻1-(1-炔基)环丙基酮的三元环使其开环形成一个烯醇负离子中间体,然后根据反应体系中存在的亲电试剂种类与数量不同,此中间体选择性地以其共轭的联烯负离子或者炔丙基负离子形式去进攻亲电试剂,生成(E)-4-烯-1,3二羰化合物、多取代联烯酮、多取代呋喃以及多取代含氟β,γ,-炔基酮等多种重要的有机小分子化合物。
2.发展了2-呋喃甲醛/胺/2-苯硒基丙烯酸和异腈参与的四组分反应。首先,这四个组分加到一起自发进行Ugi反应生成了β-酰胺基酰胺,此时,由于产物内恰当位置同时含有缺电子的烯烃和富电子的呋喃,在室温或者加热的条件下又会进一步发生Diels-Alder反应生成三环内酰胺化合物,通过往反应体系中加入三氟化硼乙醚,接下来依次发生的氧桥开环苯硒基消除和芳构化反应最终一锅法合成了多取代异吲哚酮类化合物。
第二部分——高分子有机硒试剂在固相有机合成中的应用
3.从聚苯乙烯负载的α-硒基-β-氨基酸酯出发,先用胺与官能团化的酸缩合,再根据酸α位官能团的不同,选择性地形成六元环或者是七元环,最后从树脂上切割下来,建立了一套固相合成2-吡啶酮,1,4-二氮杂草,和氧代1,4-二氮杂(?)化合物的方法。特别值得一提的是当使用的是手性的α-氨基酸时,其手性可以一直从原料中保持到最终的产物中,换言之就是可以使用价格低廉的天然氨基酸很便捷地合成一系列光学纯的1,4-二氮杂(?)类化合物。
4.从聚苯乙烯负载的α-硒基丙烯酸甲酯出发,先与甲亚胺叶立德发生1,3-偶极环加成反应,再经过进一步的乙内酰脲、2,5-二酮哌嗪环化反应,最后通过过氧化氢氧化消除树脂上切割下来,方便地合成了3个3-吡咯啉,3-吡咯啉并乙内酰脲和3-吡咯啉并2,5-二酮哌嗪的小分子化合物库。
The development of multi-component reactions and combinatorial chemistry enhances the efficiency of synthesis of diversified compounds, thus producing less wastes. As a result, these two new approaches have been shown with many applications in modern organic chemistry. Selenium is discovered to be an essential element for mammalian life. At the meantime, organoselenium reagents are wildly used in organic synthesis.
Based on the unique reactivities of organoselenium reagents, we have established several methods to prepare target molecules which may have potential biological or medicinal activities in a straightforward and efficient way.
This dissertation mainly includes two parts:
PartⅠ——The application of solution-phase organoselenium reagents in multi-component reactions
1. A novel three-component reaction of lithium selenolates with 1-(1-alkynyl) cyclopropyl ketones and electrophiles was developed. In this reaction, initially the lithium selenolates attack the 1-(1-alkynyl)cyclopropyl ketones to open the cyclopropane rings, then electrophiles were used to capture the formed carboanions to furnish the corresponding products. By changing the electrophiles, we can obtain (E)-4-alken-1,3-diketones,1,2-allenic ketones, furans, and fluorine substituted 1-alkynyl ketones, respectively.
2.2-Furylaldehydes, amines,2-(phenylselenyl)acrylic acids, and isocyanides were used to perform a Ugi-type four-component condensation reaction. Then at room temperature or under reflux, the corresponding products underwent a further Diels-Alder cycloaddition reaction. Promoted by BF3·OEt2, sequential oxygen bridge opening, phenylselenyl elimination, and aromatization of the Diels-Alder products finally gave the highly substituted isoindolinones.
PartⅡ——The application of resin-bound organoselenium reagents in solid-phase organic synthesis
1. The polystyrene-supported a-seleno-β-amino esters were used to react with a-functionalized acids to form the corresponding amide resins. According to the differences of functional group on the acids, six and seven-membered rings were formed respectively. After cleavage from the resins, we could prepare three libraries of 2-pyridones,1,4-diazepines, and 1,4-oxazepines. It should be noted that when natural a-amino acids were used, optically pure 1,4-diazepines would be given as the expected products.
2. The resin-bound a-seleno methyl acrylates were used to undergo 1,3-dipolar cycloaddition with azomethine ylides to furnish polystyrene-supported pyrrolidine-substituted selenide resins. Then further reactions took places on these resins to construct the hydantoin and 2,5-diketopiperazine rings. After oxidation and elimination of the selenides, the corresponding 3-pyrrolines, 3-pyrroline-fused hydantoins, and 3-pyrroline-fused 2,5-diketopiperazines were released from the resins in moderate yields and good purities.
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