{"title":"绿色通道下的高效异质 Ni-phen MCM-41 混合配体复合物演化出具有生物活性的 3,4-二氢嘧啶-2(1H)-酮类化合物","authors":"Narmatha Venkatesan, Bharathi Madheswaran, Anandha Abirami Govindan, Denzil Britto Christopher Leslee, Jayapratha Gunasekaran, Shanmuga Bharathi Kuppannan","doi":"10.1007/s11164-024-05350-1","DOIUrl":null,"url":null,"abstract":"<div><p>The synthesis of 3,4-dihydropyrimidin-2-(1<i>H</i>)-ones (DHPMs) was made by utilizing newly synthesized heterogeneous mixed ligand-based Ni-phen MCM-41 catalyst with variety of aryl aldehydes (viz. electron donating, electron withdrawing, fused, disubstituted and unsaturated substituents), ethylacetoacetate, urea and ethanol as a solvent by using two different energy sources: conventional and ultrasonication methods. The effectiveness of the two methods was compared and found that the formation of Biginelli products in ultrasonication method (65–92% yield at 60 °C, 45 min) is better than the conventional method (63–90% yield at 78 °C, 2 h) by yield, temperature and time of the reaction. The formation, heterogeneous nature and morphology of the catalyst have been characterized by Fourier transform infrared spectroscopy (FT-IR), powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), inductively coupled plasma-optical emission spectrometry (ICP-OES), thermogravimetric analysis (TGA) and N<sub>2</sub> adsorption–desorption isotherm (BET) techniques. Moreover, the catalyst was recoverable, reusable and very much efficient for three consecutive runs without any significant loss of its catalytic activity. The heterogeneity nature of the recovered catalyst was checked by hot filtration test.</p><h3>Graphical abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":753,"journal":{"name":"Research on Chemical Intermediates","volume":"50 9","pages":"4315 - 4335"},"PeriodicalIF":2.8000,"publicationDate":"2024-07-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Evolution of bioactive 3, 4-dihydropyrimidin-2(1H)-ones by an efficient heterogeneous Ni-phen MCM-41 mixed ligand complex under green path\",\"authors\":\"Narmatha Venkatesan, Bharathi Madheswaran, Anandha Abirami Govindan, Denzil Britto Christopher Leslee, Jayapratha Gunasekaran, Shanmuga Bharathi Kuppannan\",\"doi\":\"10.1007/s11164-024-05350-1\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>The synthesis of 3,4-dihydropyrimidin-2-(1<i>H</i>)-ones (DHPMs) was made by utilizing newly synthesized heterogeneous mixed ligand-based Ni-phen MCM-41 catalyst with variety of aryl aldehydes (viz. electron donating, electron withdrawing, fused, disubstituted and unsaturated substituents), ethylacetoacetate, urea and ethanol as a solvent by using two different energy sources: conventional and ultrasonication methods. The effectiveness of the two methods was compared and found that the formation of Biginelli products in ultrasonication method (65–92% yield at 60 °C, 45 min) is better than the conventional method (63–90% yield at 78 °C, 2 h) by yield, temperature and time of the reaction. The formation, heterogeneous nature and morphology of the catalyst have been characterized by Fourier transform infrared spectroscopy (FT-IR), powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), inductively coupled plasma-optical emission spectrometry (ICP-OES), thermogravimetric analysis (TGA) and N<sub>2</sub> adsorption–desorption isotherm (BET) techniques. Moreover, the catalyst was recoverable, reusable and very much efficient for three consecutive runs without any significant loss of its catalytic activity. 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引用次数: 0
摘要
利用新合成的异质混合配体基 Ni-phen MCM-41 催化剂与多种芳基醛(即供电子、退电子、融合、二取代和不饱和取代基)、乙酰乙酸乙酯、尿素和乙醇作为溶剂,通过常规和超声两种不同的能量来源合成了 3,4-二氢嘧啶-2-(1H)-酮 (DHPMs)。比较两种方法的效果后发现,通过产率、温度和反应时间,超声法形成的 Biginelli 产物(60 ℃、45 分钟时产率为 65-92%)优于传统法(78 ℃、2 小时时产率为 63-90%)。傅立叶变换红外光谱(FT-IR)、粉末 X 射线衍射(PXRD)、扫描电子显微镜(SEM)、能量色散 X 射线光谱(EDX)、电感耦合等离子体-光发射光谱(ICP-OES)、热重分析(TGA)和 N2 吸附-解吸等温线(BET)技术对催化剂的形成、异质性和形态进行了表征。此外,该催化剂可回收、可重复使用,而且连续三次运行都非常有效,催化活性没有明显下降。热过滤试验检验了回收催化剂的异质性。
Evolution of bioactive 3, 4-dihydropyrimidin-2(1H)-ones by an efficient heterogeneous Ni-phen MCM-41 mixed ligand complex under green path
The synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (DHPMs) was made by utilizing newly synthesized heterogeneous mixed ligand-based Ni-phen MCM-41 catalyst with variety of aryl aldehydes (viz. electron donating, electron withdrawing, fused, disubstituted and unsaturated substituents), ethylacetoacetate, urea and ethanol as a solvent by using two different energy sources: conventional and ultrasonication methods. The effectiveness of the two methods was compared and found that the formation of Biginelli products in ultrasonication method (65–92% yield at 60 °C, 45 min) is better than the conventional method (63–90% yield at 78 °C, 2 h) by yield, temperature and time of the reaction. The formation, heterogeneous nature and morphology of the catalyst have been characterized by Fourier transform infrared spectroscopy (FT-IR), powder X-ray diffraction (PXRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), inductively coupled plasma-optical emission spectrometry (ICP-OES), thermogravimetric analysis (TGA) and N2 adsorption–desorption isotherm (BET) techniques. Moreover, the catalyst was recoverable, reusable and very much efficient for three consecutive runs without any significant loss of its catalytic activity. The heterogeneity nature of the recovered catalyst was checked by hot filtration test.
期刊介绍:
Research on Chemical Intermediates publishes current research articles and concise dynamic reviews on the properties, structures and reactivities of intermediate species in all the various domains of chemistry.
The journal also contains articles in related disciplines such as spectroscopy, molecular biology and biochemistry, atmospheric and environmental sciences, catalysis, photochemistry and photophysics. In addition, special issues dedicated to specific topics in the field are regularly published.