Silicotungstic acid nanoparticles dispersed in the micropores of Cr-pillared clay as efficient heterogeneous catalyst for the solvent free synthesis of 1,4-dihydropyridines

Kar, Purabi; Mishra, Braja Gopal

doi:10.1016/j.cej.2013.03.050

Cited by 31 publications

(5 citation statements)

References 41 publications

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“…1. 3 [47] 、自组装有序介孔纳米 SnPO 4 (HSnP-2) [48] 、纳米 Fe 3 O 4 [49] 、纳米 Fe 3 O 4 负载壳聚糖(Fe 3 O 4 @chitosan) [50] 、纳米 Fe 3 O 4 负载 SiO 2 (Fe 3 O 4 @SiO 2 ) [51] 、Fe 3 O 4 构建的磁性碳纳米管负载壳聚糖(CS-MCNTs) [52] 、纳米 MgO [53] 、纳米 ZnO [54] 、纳米 CuI [55] 、纳米 CuFe 2 O 4 [56] 、三氧化钨纳米颗粒负载磺酸(n-WSA) [57] 、硅钨酸纳米颗粒负载 Cr 交联黏土 [58] 和纳米晶体固体酸硫酸化氧化锆 [59] 环境友好、对设备无腐蚀和易于回收循环使用等特点, 因而称为清洁工艺 [60,61] . 将强酸或腐蚀性催化剂负载于适宜的载体上, 有利于催化剂充分分散、操作简便和后处理方便, 并保留甚至增强催化活性的效果.…”

Section: 基于无溶剂的 Hantzsch 反应unclassified

Progress in Synthesis of 1,4-Dihydropyridines

Lingling,

Hui,

Pan

et al. 2016

Chinese Journal of Organic Chemistry

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1,4-Dihydropyridines (1,4-DHPs) are an important class of heterocyclic compounds, and possess a broad array of biological activities and applications. With the development of green organic synthetic chemistry, some important achievements have been made in the green synthesis of 1,4-DHPs and new synthetic methods, which made up some shortcomings of the traditional synthesis of Hantzch reaction, such as environment friendly, synthesis efficiency, single product structure and lack of reaction type. This review provides the first overview for the green synthesis of Hantzch reaction and new synthetic methods of 1,4-DHPs since 2010. A comprehensive and up-to-date introduction are given for Hantzch reaction under geen solvent, geen catalyst and geen synthetic technology, and the new reaction of synthesis of 1,4-DHPs based on new building blocks. A thorough analysis is provided concerning the feature of improvement of green synthesis of Hantzsch reaction and new synthetic method. Moreover, the substrates, conditions, selectivities and yields have been also described. Finally, a brief discussion relating to developments and potential areas of further research concerning new synthetic methods of 1,4-DHPs and green synthesis, and chiral synthesis, is presented. Keywords 1,4-dihydropyridines; Hantzsch reaction; clean synthesis; enaminone 1,4-二氢吡啶(1,4-DHPs)是一类重要的含氮杂环化合物, 具有广泛的生理活性和应用价值. 其中最重要的是临床上作为钙离子通道阻滞剂治疗心脑血管和高血压等疾病 [1] , 例如, 尼卡地平(Nicardipine, 1)、尼莫地平 (Nimodipine, 2)、尼非地平(Nifedipine, 3)和非洛地平 (Felodipine, 4)等. 作为药物或药物中间体它们还具有抗人类免疫缺陷病毒(HIV) [1c,2] 、抗菌 [3] 、抗惊厥 [4] 、抗肿瘤(化合物 5) [5] 、神经保护 [6] 、辐射防护 [7] 等生物活性 [8] , 可用于合成各种各样含氮杂环化合物 [9] . 在合成中, 可作为氢源应用于众多的有机还原反应(如 Hantzsch 酯, 6) [10] (图 1). 因此, 对 1,4-DHPs 的研究十分活跃, 一直以来受到科研工作者的广泛关注.1,4-DHPs 的传统合成策略是 Hantzsch 反应的"一锅法" 合成, 于 1881 年 Hantzsch [11] 最早报道的两分子 β-羰基酸酯、一分子醛和一分子氨发生缩合反应得到 (Scheme 1). 反应经一分子 β-羰基酸酯和醛反应生成 α,β-不饱和化合物, 与另一分子 β-羰基酸酯和氨反应生成的 β-胺基烯酸酯发生 Micheal 加成反应, 再脱去一分

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Section: 基于无溶剂的 Hantzsch 反应unclassified

Progress in Synthesis of 1,4-Dihydropyridines

Lingling,

Hui,

Pan

et al. 2016

Chinese Journal of Organic Chemistry

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“…1,4-DHPs as one of the main classes of heterocycles have extensive domain of biological activities such as antibacterial, antitumor, anti-inflammatories, vasodilator, anti-atherosclerotic, antidiabetic anticonvulsant, antithrombotic and calcium channel blockers. [12][13][14][15][16][17][18][19] Among the dicarbonyl compounds, tetronic acid can be mentioned as a structural moiety in some of the natural compounds such as muconolactones, acetogenins, strigol and leptosfaerin. [20,21] Due to some features of these compounds such as antibiotic, HIV-1 protease inhibitors, antiepileptic, anticoagulant, antibacterial, antifungal, analgesic, anti-inflammatory, and anticancer, could be considered as interesting templates for medicinal chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, much attention has been paid to the synthesis of 1,4‐dihydropyridines (1,4‐DHPs), which are heterocycles containing nitrogen atoms. 1,4‐DHPs as one of the main classes of heterocycles have extensive domain of biological activities such as antibacterial, antitumor, anti‐inflammatories, vasodilator, anti‐atherosclerotic, antidiabetic anticonvulsant, antithrombotic and calcium channel blockers …”

Section: Introductionmentioning

confidence: 99%

Synthesis of New and Highly Functionalized 1,4‐Dihydropyridines and Spirooxindole Dihydropyridines Using L‐Proline as Efficient Catalyst

Neamani

Moradi

2020

ChemistrySelect

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Herein, eco-friendly, mild and efficient synthesis of a new type of 1,4-dihydropyridines and some of the spirooxoindole dihydropyridine derivatives was developed by using L-proline as an effective homogeneous catalyst. The one-pot multicomponent reaction of malononitrile, different anilines, and benzaldehydes were performed in the presence of Water/EtOH (1 : 1) as solvent at 90°C and furnished the corresponding products in high yields. Further, we developed a threecomponent one-pot reaction of malononitrile, anilolactone, and differently substituted isatins to afford new spirooxindole dihydropyridine derivatives using the same catalyst and conditions. All of the obtained products were characterized by spectroscopic and analytical techniques.

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“…A series of dihydropyridines (35) were synthesized using a series of aldehydes, 1,3-diketo compounds and ammonium acetate or amines under solvent-free MW conditions. Silicotungstic acid nanoparticles dispersed in the micropores of Cr-pillared clay (STA/Cr-P) were used as heterogeneous catalysts for the solvent-free synthesis of 1,4-dihydropyridines (36 or 37) (Scheme 2.28) [52]. During these reactions, aryl aldehydes or chalcones were reacted with ethyl acetoacetate and ammonium acetate under continuous MW irradiation at 900 W. After regeneration, the STA/Cr-P catalyst was re-usable for several times.…”

Section: Hantzsch Reactionsmentioning

confidence: 99%

Microwave-Assisted Syntheses in Organic Chemistry

Kiss

Bálint²,

Keglevich

2016

SpringerBriefs in Molecular Science

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The second part focuses on the summary of typical organic chemical reactions selected, such as coupling reactions (C-C bond formation reactions, carbon-heteroatom bond formations), condensations (aldol-type-, Claisen-, Knoevenagel reaction), multicomponent reactions (Mannich-, Biginelli-, Hantzsch-, Bucherer-Bergs-, Strecker-, Gewald-, Kabachnik-Fields-, Kindler-, Passerini-, Ugi-and domino reactions), cycloadditions (including Diels-Alder reactions). The authors tried to compile fashionable reactions that have been reviewed less in the past years.

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Silicotungstic acid nanoparticles dispersed in the micropores of Cr-pillared clay as efficient heterogeneous catalyst for the solvent free synthesis of 1,4-dihydropyridines

Cited by 31 publications

References 41 publications

Progress in Synthesis of 1,4-Dihydropyridines

Progress in Synthesis of 1,4-Dihydropyridines

Synthesis of New and Highly Functionalized 1,4‐Dihydropyridines and Spirooxindole Dihydropyridines Using L‐Proline as Efficient Catalyst

Microwave-Assisted Syntheses in Organic Chemistry

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