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基于N-炔磺酰胺的氮杂环合成
论文作者:童鞋论文网  论文来源:www.txlunwenw.com  发布时间:2019/11/1 9:06:49  

摘要:N-炔磺酰胺官能团通过氮原子活化碳三键,使得炔烃同时具有亲电和亲核性质。通过选择氮取代的吸电子基团,研究者们可以调节N-炔磺酰胺的电子特性和反应性,使其组合成多功能的合成前体。N-炔磺酰胺可以直接反应得到含氮杂环产品,提供了获得天然产物和具有药用价值的分子中间体的重要方法。因此,研究人员近年来已经投入了越来越多的时间研究关于N-炔磺酰胺的化学。本文内容主要分为以下两个方面:

(1)利用二烯磺酰胺类化合物和炔溴结构在铜催化的作用下得到N-炔磺酰胺中间体,这个中间体会立刻发生分子内Diels–Alder反应,可以认为这个反应为逆电子需求的[4+2]环加成反应,这样就通过一锅两步的方法高效的得到十九种不同的4,7-顺式四氢吲哚,产率在47%-82%。这个方法提供了一个能容易合成复杂多环生物碱的策略,并且具有廉价,高效可持续的优点。产物中的四氢吲哚结构还能发生氧化,双羟化等一系列反应,四氢吲哚是高附加值的产品,可进一步衍生,获得更多有用的医药中间体。

(2)首次运用具有烯烃结构的N-炔磺酰胺类化合物在银催化的条件下,通过加热,发生分子内的Ⅱ型Alder烯反应得到十四种不同的八氢异喹啉含氮杂环产品,产率在40%-70%。并通过单晶结构,确定了相对构型,实现了一类结构丰富的氮杂环的合成。这些产品有望进一步拓展底物范围,并开发产品衍生化,获得更多更有用的医药中间体。

总之,本文第一次发展了铜催化N-炔磺酰胺形成/[4+2]环加成串联反应,以较高的产率合成了一系列高立体选择性的四氢吲哚含氮杂环化合物。经过该反应的启发,从而认为N-炔磺酰胺还有很大的研究空间,于是通过制备含烯烃的N-炔磺酰胺作为前体,在硫酸银的催化下成功的发生了Ⅱ型Alder烯反应得到相应的八氢异喹啉结构化合物,这些氮杂环产品都是有用的医药中间体前体,对进一步的深入研究有很大的意义。可以看出N-炔磺酰胺类化合物反应活性很强,仍有很大的研究空间,对医药行业提供了有用的理论前提。

The ynamide functional group activatescarbon triple bonds through an attached nitrogen atom that carbon bears anelectron-withdrawing group. As a result, the alkyne has both electrophilic andnucleophilic properties. Through the selection of the electron-withdrawinggroup attached to nitrogen, chemists can modulate the electronic properties andreactivity of ynamides, making these groups versatile synthetic buildingblocks. The reactions of ynamides also lead directly to nitrogen-containingproducts, which provides access to important structural motifs found in naturalproducts and molecules of medicinal interest. Therefore, researchers haveinvested increasing time and research in the chemistry of ynamides in recentyears. This paper mainly divided into the following two aspects:

(1) Dienesulfonamide compounds andbromoalkyne structures can react to obtain the Ynamide intermediate under thecatalysis of copper, which was used immediately in an intramolecularDiels-Alder reaction to furnish nineteen 4,7-cis-tetrahydroindolines withexcellent stereoselectivity in 47%-82% yields. This method of a one-pottwo-step had the advantages of being cheap, efficient, and sustainable, andprovided facile entry to complex polycyclic alkaliods which can be furtherelaborated by oxidation and dihydroxylation of the alkene group,tetrahydroindolines is a high value-added product that can be further derivatizedto obtain more useful pharmaceutical intermediates.

(2) For the first time, undersilver-catalyzed and thermal conditions, we have used ynamide with olefin tofurnish fourteen corresponding hexahydroisoquinoline compounds by anintramolecular Type II Alder ene reactions in 40%-70% yields. We also got therelative stereochemistry of the product by X-ray crystal structure, to realizethe synthesis of a class of structurally rich nitrogen heterocycles. Subsequentresearch is expected to further expand the scope of substrates and developproduct derivatization to obtain more useful pharmaceutical intermediates.

In summary, the first a one-potcopper-catalyzed ynamide/[4+2] cycloaddition cascade has been developed, thusproving a highly facile protocol for stereoselective assembly of a series oftetrahydroindolines at relatively high yields. Inspired by this reaction, webelieve that there is still much research space for ynamides, so we havedevelopde a intramolecular type II Alder ene reaction of ynamide with olefin bycatalysis of silver give a series of hexahydroisoquinoline compounds. Thesenitrogen heterocyclic products are useful precursors of pharmaceuticalintermediates and have great significance for further research. It can be seenthat the N-acetylene sulfonamide compounds are very reactive and still have alot of research space, which provides a useful theoretical premise for thepharmaceutical industry.

关键词:N-炔磺酰胺;铜催化;两步一锅;Diels-Alder反应;Alder烯反应

ynamide; copper catalyze; one-pot;Diels–Alder reaction; Alder ene reactive

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