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Synthesis and Antibacterial Screening of Some Pyrazole Derivatives Catalyzed by Cetyltrimethylammoniumbromide (CTAB)
Current Organic Synthesis ( IF 1.8 ) Pub Date : 2021-02-28 , DOI: 10.2174/1570179417666200620220232
Ravi Bansal 1 , Pradeep K Soni 1 , Neha Gupta 2 , Sameer S Bhagyawant 2 , Anand K Halve 1
Affiliation  

Aims: In this article, we have developed an eco-friendly one-pot multi-component reaction methodology employed for the green synthesis of functionalized pyrazole derivatives viz cyclo-condensation of aromatic aldehydes, ethyl acetoacetate and phenyl hydrazine and/or hydrazine hydrate in the presence of cetyltrimethylammoniumbromide (CTAB) at 90°C temperature in an aqueous medium.

Materials and Methods: In the present protocol, we developed a green method for the synthesis of functionalized pyrazole derivatives through one-pot, multi-component cyclo-condensation of aromatic aldehydes, phenyl hydrazine or hydrazine hydrate and ethyl acetoacetate using cetyltrimethylammoniumbromide (CTAB) as a catalyst in water as a solvent. Our methodology confers advantages such as short reaction time, atom economy, purification of the product without using column chromatographic and hazardous solvent. The reaction is being catalyzed by cetyltrimethylammoniumbromide (CTAB) and thus, products are formed under the green reaction conditions.

Results and Discussion: Initially, the reaction of benzaldehyde and phenylhydrazine with ethyl acetoacetate was carried out in water at room temperature in the absence of the catalyst; no product was obtained after 24 h. When the reaction was carried out using L-proline as a catalyst in ethanol at 70°C, the yield of the product was 20%.

Conclusion: This research not only provides a green and efficient method for the synthesis of sulfinic esters but also shows new applications of electrochemistry in organic synthesis. We consider that this green and efficient synthetic protocol used to prepare sulfinic esters will have good applications in the future. In conclusion, we have developed successfully a green and efficient one-pot multi-component methodology for the synthesis of substituted pyrazoles using CTAB as a catalyst in water as a solvent with excellent yields. Purifications of compounds were achieved without the use of traditional chromatographic procedures. This methodology has advantages of operational simplicity, clean reaction profiles and relatively broad scope, which make it more attractive for the diversity oriented synthesis of these heterocyclic libraries. In this methodology, we suggest a further alternative possibility for the formation of substituted pyrazoles. The compound 7h can be used as an anticancer drug in the pharma industry.



中文翻译:

十六烷基三甲基溴化铵(CTAB)催化一些吡唑衍生物的合成及抗菌筛选

目的:在本文中,我们开发了一种环保的一锅多组分反应方法,用于功能化吡唑衍生物的绿色合成,即芳香醛、乙酰乙酸乙酯和苯肼和/或水合肼在在 90°C 温度下在水性介质中存在十六烷基三甲基溴化铵 (CTAB)。

材料和方法:在本协议中,我们开发了一种绿色方法,通过使用十六烷基三甲基溴化铵 (CTAB) 作为芳香醛、苯肼或水合肼和乙酰乙酸乙酯的单锅、多组分环缩合反应合成功能化吡唑衍生物。以水为溶剂的催化剂。我们的方法具有反应时间短、原子经济性、产品纯化无需使用柱色谱和有害溶剂等优点。该反应由十六烷基三甲基溴化铵(CTAB)催化,因此在绿色反应条件下形成产物。

结果与讨论: 最初,苯甲醛和苯肼与乙酰乙酸乙酯的反应是在室温下在没有催化剂的情况下在水中进行的;24 小时后未获得产品。以L-脯氨酸为催化剂,在70℃乙醇中进行反应,产物收率为20%。

结论:本研究不仅为亚磺酸酯的合成提供了一种绿色高效的方法,而且展示了电化学在有机合成中的新应用。我们认为这种用于制备亚磺酸酯的绿色高效合成方案在未来会有很好的应用。总之,我们已经成功地开发了一种绿色、高效的单锅多组分方法,用于以 CTAB 为催化剂,以水为溶剂合成取代吡唑,收率极好。无需使用传统色谱程序即可实现化合物的纯化。该方法具有操作简单、反应清晰、适用范围相对较广的优点,使其对这些杂环库的多样性导向合成更具吸引力。在这种方法中,我们建议形成取代吡唑的另一种可能性。化合物7h可在制药工业中用作抗癌药物。

更新日期:2021-03-05
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