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首页> 外文期刊>RSC Advances >Environmentally benign and diastereoselective synthesis of 2,4,5-trisubstituted-2-imidazolines
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Environmentally benign and diastereoselective synthesis of 2,4,5-trisubstituted-2-imidazolines

机译：2,4,5-三取代-2-咪唑啉的环境良性和非对映选择性合成

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摘要

2-Imidazolines are heterocycles with a wide range of applications in biomedical science, pharmaceuticals, surfactants and catalysis. The 2,4,5-trisubstituted derivatives are conventionally prepared through the reaction of aromatic aldehydes and ammonia, requiring harsh conditions and toxic solvents. Herein, we report a sustainable, one-pot synthetic route to obtain cis or trans diastereomers of 2,4,5-trisubstituted-2-imidazolines. The reaction parameters, such as the ammonia source, the substituents of the aromatic aldehydes and the effect of temperature and solvent, were systematically explored. The synthesis was attempted in sixteen different green solvents. Reaction kinetics and quantum mechanical studies (DFT B3LYP/6-31G(d,p)) revealed the elementary steps of the cyclisation and refuted two common speculations. The limitations of the synthesis were explored through varying the p-, o-, and m-substituents on the aldehyde as well as employing heterocyclic and non-aromatic derivatives. Ten out of the twelve products synthesised in this work can be solely purified by crystallisation, without the need for extraction or chromatography. Owing to the bulky nature of the products, the applicability of membrane-based purification was demonstrated to further improve the sustainability of the synthesis.
机译：2-咪唑啉是杂环，在生物医学，药物，表面活性剂和催化领域具有广泛的应用。通常通过需要苛刻条件和有毒溶剂的芳族醛与氨反应制备2,4,5-三取代衍生物。在这里，我们报告了一种可持续的一锅法合成路线，以获得2,4,5-三取代-2-咪唑啉的顺式或反式非对映异构体。系统地探讨了氨源，芳醛的取代基，温度和溶剂的影响等反应参数。尝试在十六种不同的绿色溶剂中进行合成。反应动力学和量子力学研究（DFT B3LYP / 6-31G（d，p））揭示了环化的基本步骤，并驳斥了两种常见的推测。通过改变醛上的 p -， o -和 m 取代基以及采用杂环和非芳族衍生物。在这项工作中合成的十二种产物中，有十种可以仅通过结晶纯化，而无需萃取或色谱分离。由于产品的大体积性质，证明了基于膜的纯化的适用性进一步提高了合成的可持续性。

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