微波辅助的吡咯有机合成(综述)

E. Mateev, Ali Irfan, Alexandrina Mateeva, M. Georgieva, A. Zlatkov
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摘要

在众多具有各种药理活性的有机化合物中发现吡咯环,凸显了其在药物化学中的巨大重要性。因此,吡咯的合成继续引起人们的兴趣,而 Paal-Knorr 缩合反应被认为是主要的合成路线。自从微波活化被引入有机合成以来,已经取得了长足的进步,这一点可以从相关论文的快速增长中得到证实。微波辐照反应时间更短、产率更高、操作更简便、能耗更低,因此越来越受到人们的青睐。此外,微波辐照还出现在许多绿色化学方案中。本文旨在深入介绍吡咯衍生物的微波合成,重点是最常用的合成方法--Paal-Knorr、Clauson-Kaas、Barton-Zard、Hantzsch 等。文章分为几个部分,首先介绍了微波有机合成的原理。随后,研究了吡咯衍生物的结构和主要药理作用。随后,讨论了通过 Paal-Knorr、Hantzsch、Clauson-Kaas 和 Barton-Zard 合成吡咯的文章。所有综述文章都得出结论,与传统加热方式相比,采用微波辐照后反应时间大大缩短。
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Microwave-assisted organic synthesis of pyrroles (Review)
The detection of pyrrole rings in numerous organic compounds with various pharmacological activities, emphasizes its huge importance in medicinal chemistry. Thus, the synthesis of pyrroles continues to arouse interest and Paal-Knorr condensation is considered to be the main synthetic route. A significant advance has been made since the MW activation was introduced in the organic synthesis which can be confirmed with the rapid growth of the published papers on that topic. Microwave irradiation is gaining popularity since faster reaction time, higher yields, easier work-up and reduced energy input can be achieved. Furthermore, it appears in numerous green chemistry protocols. The aim of the current article was to provide insights into the microwave syntheses of pyrrole derivatives, focusing on the most used synthetic approaches - Paal-Knorr, Clauson-Kaas, Barton-Zard, Hantzsch and others. The article was divided into several sections starting with the principles of the microwave organic synthesis. Thereafter the structure and the main pharmacological effects of the pyrrole derivatives were examined. Subsequently, articles describing the synthesis of pyrroles via Paal-Knorr, Hantzsch, Clauson-Kaas and Barton– Zard were discussed. All the reviewed papers conclude a significant reduction of the reaction times after MW irradiation compared to conventional heating.
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