Synthesis of hexahydroquinoline (HHQ) derivatives using ZrOCl2 center dot 8H(2)O as a potential green catalyst and optimization of reaction conditions using design of experiment (DOE)

Khazaei Ardeshir; Sarmasti Negin; Seyf Jaber Yousefi; Tavasoli Mahsa

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Synthesis of hexahydroquinoline (HHQ) derivatives using ZrOCl2 center dot 8H(2)O as a potential green catalyst and optimization of reaction conditions using design of experiment (DOE)

机译：使用ZrOCl2中心点8H（2）O作为潜在的绿色催化剂合成六氢喹啉（HHQ）衍生物和使用实验设计（DOE）优化反应条件

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In this investigation, hexahydroquinoline (HHQ) derivatives were synthesized via a one-pot reaction using dimedone, beta-ketoester, ammonium acetate, and different aryl aldehydes. ZrOCl2 center dot 8H(2)O was used as a potential green catalyst, it is a commercially available solid material, with low toxicity, low cost and high activity, and it is easy to handle. The reaction conditions were optimized using response surface methodology (Central Composite Design (CCD)) with three replicates at a central point. Optimization showed that the optimum reaction temperature and amount of catalyst are 83.75 degrees C and 0.15 mol%, respectively. The lower reaction yields at temperatures higher than 83.75 degrees C are related to the formation of a new crystalline phase of ZrOCl2 center dot 8H(2)O. The fitted quadratic polynomial model applied to the experimental yield could well predict the experimental reaction yield. Ecofriendly reaction conditions, easy workup procedure, the reusability of the catalyst, short reaction times and high yields are some of the advantages of this work.

机译：在这项研究中，六氢喹啉（HHQ）衍生物是通过使用一丁二酮，β-酮酸酯，乙酸铵和不同的芳基醛进行一锅反应合成的。 ZrOCl2中心点8H（2）O被用作潜在的绿色催化剂，它是一种可商购的固体材料，具有低毒性，低成本和高活性，并且易于处理。使用响应面方法（中央复合设计（CCD））优化反应条件，并在一个中心点进行三个重复。优化表明，最佳反应温度和催化剂用量分别为83.75℃和0.15mol％。在高于83.75摄氏度的温度下，较低的反应产率与ZrOCl2中心点8H（2）O的新结晶相的形成有关。将拟合的二次多项式模型应用于实验产率可以很好地预测实验反应产率。环保的反应条件，简便的后处理步骤，催化剂的可重复使用性，较短的反应时间和高收率是这项工作的一些优点。

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《RSC Advances》 |2015年第123期|共8页
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Khazaei Ardeshir; Sarmasti Negin; Seyf Jaber Yousefi; Tavasoli Mahsa;
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1. Synthesis of hexahydroquinoline (HHQ) derivatives using ZrOCl2 center dot 8H(2)O as a potential green catalyst and optimization of reaction conditions using design of experiment (DOE) [J] . Khazaei Ardeshir, Sarmasti Negin, Seyf Jaber Yousefi, RSC Advances . 2015,第123期

机译：使用ZrOCl2中心点8H（2）O作为潜在的绿色催化剂合成六氢喹啉（HHQ）衍生物和使用实验设计（DOE）优化反应条件
2. ZrOCl2 center dot 8H(2)O as an efficient and recyclable catalyst for the one-pot multicomponent synthesis of novel [1,3]oxazino[5,6-c]quinolin-5-one derivatives [J] . Han Liangliang, Zhou Zhongqiang Applied Organometallic Chemistry . 2019,第4期

机译：Zrocl2中心点8h（2）o作为一种新型的一盆多组分合成的高效且可回收的催化剂[1,3]恶益[5,6-c]喹啉-5-一种衍生物
3. ZrOCl2 center dot 8H(2)O as an efficient catalyst for the synthesis of dibenzo [b,i]xanthene-tetraones and fluorescent hydroxyl naphthalene-1,4-diones [J] . Tavakoli Hamid Reza, Moosavi Sayed Mojtaba, Bazgir Ayoob Research on Chemical Intermediates . 2015,第5期

机译：ZrOCl2中心点8H（2）O作为合成二苯并[b，i]蒽并四酮和荧光羟基萘-1,4-二酮的有效催化剂
4. Optimization of Protein PEGylation Reaction using Design of Experiments (DOE) and Kinetic Modeling [C] . Amol Ketkar, Donna Lee, Ping Yeh, Controlled Release Society annual meeting . 2004

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5. New developments toward the synthesis of heterocycles and applications in green chemistry. I. A simple and essentially one-pot synthesis of N-aminated heterocycles using phase transfer catalyst (Aliquat-336). II. Synthesis of pharmaceutically important pyrrole derivatives. III. Applications in green chemistry: Surfactant-mediated environmentally friendly cleavage of aromatic esters and trans-esterification under solvent-free neutral conditions . [D] . Patel, Nitinchandra. 2005

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Synthesis of hexahydroquinoline (HHQ) derivatives using ZrOCl2 center dot 8H(2)O as a potential green catalyst and optimization of reaction conditions using design of experiment (DOE)

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