Greener and practical synthesis of 4,4′‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol)s through a conventional heating and a mechanochemical procedure,Journal of Heterocyclic Chemistry

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Greener and practical synthesis of 4,4′‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol)s through a conventional heating and a mechanochemical procedure
Journal of Heterocyclic Chemistry ( IF 2.0 ) Pub Date : 2020-08-03 , DOI: 10.1002/jhet.4113
Nader Ghaffari Khaligh ₁ , Taraneh Mihankhah ₂

Affiliation

A new catalytic application of 4,4′‐trimethylenedipiperidine for the efficient synthesis of 4,4′‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol)s is developed. According to the principles of green chemistry, the reaction was performed by conventional and non‐conventional processes: (a) in the refluxing ethanol using a catalytic amount of organocatalyst; (b) at room temperature in the presence of organocatalyst in a planetary ball mill under solvent‐free conditions. The organocatalyst could be reused up to 10 runs, and a negligible reduction of catalytic activity was detected. A variety of substituted 4,4′‐(arylmethylene)bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐ol)s were obtained in good–to‐excellent yields under eco‐friendly conditions. 4,4′‐Trimethylenedipiperidine is commercially available and easy to handle and storage, less toxic, non‐flammable, as well as it shows high thermal stability and good solubility in water. The current methodology has merits including (a) wide substrate‐scope and high yields of the desired products in the short reaction times, (b) avoiding the use of hazardous solvents and acidic and metal‐containing catalysts, (c) minimize the generation of hazardous waste, and (d) simple workup process. Based on great potential as a promising organocatalyst, we hope it can be used as a greener alternative to piperidine for other organic transformations.

中文翻译：

通过常规加热和机械化学方法更环保，更实用地合成4,4'-（芳基亚甲基）双（3-甲基-1-苯基-1H-吡唑-5-醇）s

开发了4,4'-三亚甲基二哌啶用于高效合成4,4'-（芳基亚甲基）双（3-甲基-1-苯基-1 H-吡唑-5-醇）s的新催化应用。根据绿色化学原理，反应通过常规方法和非常规方法进行：（a）使用催化量的有机催化剂在回流的乙醇中进行；（b）在室温下，在无溶剂条件下，在行星式球磨机中存在有机催化剂的情况下。该有机催化剂最多可重复使用10次，并且催化活性的降低可忽略不计。各种取代的4,4'-（芳基亚甲基）双（3-甲基-1-苯基-1 H在生态友好的条件下以良好至优异的产量获得了吡唑-5醇。4,4'-三亚甲基二哌啶可商购获得，易于处理和储存，毒性小，不易燃，并且显示出高热稳定性和在水中的良好溶解性。当前的方法具有以下优点：（a）较宽的底物范围和较短的反应时间内所需产物的高收率；（b）避免使用有害溶剂以及酸性和含金属的催化剂；（c）最大限度地减少了危险废物，以及（d）简单的后处理过程。基于作为有前途的有机催化剂的巨大潜力，我们希望它可以用作哌啶的绿色替代品，用于其他有机转化。

更新日期：2020-08-03

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