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首页> 外文期刊>Computational Chemistry >Conversion of 3,4-Dihydroxypyrrolidine-2,5-Dione to Maleimide through Tosylation and Mechanism Study by DFT
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Conversion of 3,4-Dihydroxypyrrolidine-2,5-Dione to Maleimide through Tosylation and Mechanism Study by DFT

机译：3,4-二羟基吡咯烷-2,5-二酮通过甲苯磺酸转化为马来酰亚胺的机理及DFT研究

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Pyrrolidine-2,5-dione and maleimide are important scaffolds of many organic substances, and their derivatives are now attracting more and more interests from researchers in organic synthesis, medicinal chemistry, and drug development. Tosyloxy (-OTs) group is an important functional group widely used in organic synthesis, because it can be readily prepared from alcohols and is an excellent leaving group. However, surprisingly, substances bearing tosyloxy groups on pyrrolidine-2,5-dione or maleimide scaffolds are very rare. In this study, we discovered that, when treated with TsCl/Et_(3)N,? trans -3,4-dihydroxypyrrolidine-2,5- dione will eliminate a TsOH molecule to form monotosyloxymaleimide. Thermodynamic and kinetic factors affecting this reaction were investigated by theoretical computation using density functional theory (DFT), and the possible reaction mechanism was proposed based on the computation results. Our results showed that tosylates of trans -3,4-dihydroxypyrrolidine- 2,5-dione, either monotosylate or ditosylate, are thermodynamically instable and may spontaneously convert to maleimides. This knowledge could be useful in understanding the properties of pyrrolidine-2,5-diones and maleimides, as well as the related organic synthesis.
机译：吡咯烷-2,5-二酮和马来酰亚胺是许多有机物质的重要支架，它们的衍生物现在引起了有机合成，药物化学和药物开发研究人员的越来越多的兴趣。甲苯氧基（-OTs）基团是有机合成中广泛使用的重要官能团，因为它可以很容易地由醇制备，并且是极好的离去基团。然而，令人惊讶地，在吡咯烷-2，5-二酮或马来酰亚胺支架上带有甲苯磺酰基的物质非常罕见。在这项研究中，我们发现当用TsCl / Et_（3）N处理时，反式-3,4-二羟基吡咯烷-2,5-二酮将消除TsOH分子以形成单甲苯磺酰氧基马来酰亚胺。利用密度泛函理论（DFT）通过理论计算研究了影响该反应的热力学和动力学因素，并根据计算结果提出了可能的反应机理。我们的结果表明，反式-3,4-二羟基吡咯烷-2,5-二酮的甲苯磺酸酯，无论是单甲苯磺酸酯还是二甲苯磺酸酯，在热力学上都是不稳定的，并且可以自发转化为马来酰亚胺。该知识可能有助于理解吡咯烷-2,5-二酮和马来酰亚胺的性质，以及相关的有机合成。

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