Tetrahedron Green Chem最新文献

英文中文

Green and traditional one-pot synthesis techniques for bioactive quinoline derivatives: A review

Tetrahedron Green Chem

Pub Date : 2025-01-02 DOI: 10.1016/j.tgchem.2025.100062

Manav C. Parmar, Bonny Y. Patel

The review examines one-pot strategies and their mechanistic approaches for synthesizing the quinoline nucleus from 2009 to 2024, with a focus on their therapeutic potential. The paradigm shifts from conventional synthetic protocols to advanced green methodologies has revolutionized the synthesis of quinoline derivatives. Strategies that adhere to sustainable chemistry principles by minimizing waste, solvent consumption, and energy input. Various green catalysts, including p-toluenesulfonic acid (p-TSA), para-sulfonic acid calix[4]arene (CX4SO₃H), cerium nitrate, ammonium acetate, potassium carbonate (K₂CO₃), and catalyst-free techniques, have proven effective in synthesizing quinoline analogs. The use of greener solvents such as ethanol and water further supports the eco-friendly synthesis of these compounds. The review also highlights a broad spectrum of pharmacological activities of quinoline derivatives, including antibacterial, antiviral, antidiabetic, anticancer properties and so on. SAR studies show that adding EDGs (-CH₃, –OCH₃, –OH) and EWGs (-Cl, –F, –NO₂, –CF₃) can enhance electronic properties, lipophilicity, and receptor-binding affinities. Moreover, hybridization with heterocyclic scaffolds such as furan, pyrazole, indole, and thiadiazole significantly improves bioactivity, demonstrating the intricate relationship between structural modifications and biological efficacy. By merging sustainable chemistry with targeted pharmacological strategies, quinoline-based compounds emerge as innovative candidates for diverse clinical applications.

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引用次数: 0

Solvent-free and eco-friendly green protocol for N-Boc Protection of amines using picric acid as a catalyst

Tetrahedron Green Chem

Pub Date : 2024-12-13 DOI: 10.1016/j.tgchem.2024.100061

Ramesha Thongolla , Ummareddy Venkata Subba Reddy , Sailam Sri Gogula , Empati Raja Sekhar , Puchakayala Muralidhar Reddy , Anren Hu

We have developed an environmentally conscious green protocol to protect amine functional groups in drug discovery and the total synthesis of biologically active natural products. This method utilizes di-tert-butyl dicarbonate ((Boc)₂O) to protect aromatic and aliphatic amines, with readily available picric acid (2 mol%) serving as a Brønsted acid catalyst. This approach enables rapid and high-yield (up to 98 %) protection of amines under completely solvent-free and eco-friendly conditions, thereby promoting a cleaner and more sustainable synthetic process.

引用次数: 0

ANO-catalyzed multicomponent synthesis of 3-nitroalkyl-N-substituted pyrroles

Tetrahedron Green Chem

Pub Date : 2024-12-08 DOI: 10.1016/j.tgchem.2024.100060

Luiz H. Dapper , Viviane T. Mena , Márcio S. Silva , Filipe Penteado , Eder J. Lenardão

A sustainable and atom-economic method was developed to prepare functionalized nitroalkyl pyrroles through a multicomponent reaction involving anilines, hexane-2,5-dione, and β-nitrostyrene derivatives. Ammonium niobium oxalate (ANO) was used as a cheap and reusable catalyst with ethanol as an eco-friendly solvent. A total of twenty-five N-substituted nitroalkyl-functionalized pyrroles were prepared in moderate to excellent yields (up to 93%). The method was successfully applied to electron-rich and electron-poor anilines, as well as to butylamine, simply by using a telescoping procedure (one-pot). Besides, the easy transformation of the obtained product in a primary amine was demonstrated.

引用次数: 0

An efficient photo-degradation of methylene blue by poly-3-thenoic acid sensitized Co/TiO2 under visible light and inactivation of pathogens

Tetrahedron Green Chem

Pub Date : 2024-12-04 DOI: 10.1016/j.tgchem.2024.100058

Neha Kumari , Sudhakar Chintakula , Immandhi Sai Sonali Anantha , Pilla Pushpavati , Suresh Maddila

Methylene blue dye is used extensively in industries, including paper, temporary hair coloring, coating for paper stock wool, and cotton dying. When the amount of methylene blue dye is more significant than 2 mg/kg, it can lead to serious health issues in people, including cyanosis, tissue necrosis, elevated heart rate, vomiting, shock, and Heinz body formation. The present chapter discusses the sol-gel-assisted synthesis of P3TA-supported Cobalt-doped TiO₂ nanohybrid. This study investigated the characteristics of both prepared bare TiO₂ and metal (Co) doped nano-hybrid using a variety of analytical tools, including XRD, SEM-EDX, BET, FTIR, XPS, and UV–visible DRS. The photo-catalytic performance of prepared samples was executed towards the degradation of methylene blue (MB) dye under visible light irradiations. Additionally, tests for antibiotic resistance were performed on the pathogens E. coli and S. aureus. Significant antibacterial activities against E. coli and S. aureus were demonstrated by the chemical under investigation (P3TA/Co-TiO₂) at a higher dosage of 800 μg/mL, with inhibition zones of 2.0 mm and 2.1 mm, respectively. The antibacterial activity against E. coli and S. aureus at 400 μg/mL was negligible, with inhibition zones of 1.0 mm and 1.2 mm, respectively. Because these materials are affordable and adaptable, they further the field of nano photo-catalysts.

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引用次数: 0

Comparing the photocatalytic activity of suspended and floating Ag-decorated TiO2 for dye removal

Tetrahedron Green Chem

Pub Date : 2024-12-04 DOI: 10.1016/j.tgchem.2024.100059

Nila Davari , Ermelinda Falletta , Claudia L. Bianchi , Viviane Yargeau , Cristina Rodriguez-Seco , Daria C. Boffito

We proposed a two-step synthesis process to fabricate floating TiO₂ and Ag-decorated TiO₂ (Ag/TiO₂) photocatalysts. In the first step, an ultrasound-assisted sol-gel method followed by spray drying was adopted to synthesize powder photocatalysts. Next, the powder samples were immobilized onto a floating polyurethane foam (PUF) support with an ultrasound-assisted impregnation method. The photocatalytic activity of TiO₂ and Ag/TiO₂ was evaluated to remove methyl orange (MO) as a dye pollutant in two suspended and floating photocatalytic systems. Ag decoration on TiO₂ improved the optical and textural properties by narrowing the bandgap energy to 2.9 eV and increasing the surface area from 10 m²/g to 30 m²/g. Ag/TiO₂ exhibited higher photocatalytic activity compared to TiO₂ for MO removal, which was 98 % for suspended and 95 % for floating catalysts under simulated sunlight irradiation. In addition, floating photocatalysts exhibited higher photocatalytic activity over five cycles of reuse. Floating Ag/TiO₂@PUF maintained 89 % of its initial photoactivity, while suspended Ag/TiO₂ lost 50 % after the five cycles. Moreover, we investigated the effect of operating conditions on the photocatalytic performance of floating Ag/TiO₂@PUF. Optimal conditions for the complete removal of MO below detection limits were obtained as follows: Ag/TiO₂@PUF loading = 0.4:200 g/mL, initial MO concentration = 5 mg/L, time = 90 min, and pH = 4 under simulated sunlight irradiation. This study highlights the potential of floating photocatalyst systems as a sustainable, reusable, and scalable approach for wastewater treatment, addressing challenges in catalyst recovery and efficiency under real-world conditions.

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引用次数: 0

Synergistic effects of hydroxyl and tertiary amine in the catalytic carbonatization of epoxides with CO2 at atmospheric pressure 羟基和叔胺在常压下催化环氧化物与二氧化碳的碳化反应中的协同效应

Tetrahedron Green Chem

Pub Date : 2024-11-08 DOI: 10.1016/j.tgchem.2024.100057

Fawaz Al Hussein , Andreas Hartwig , Henning Großekappenberg

Fixation of carbon dioxide is a key issue for the sustainable synthesis of chemical compounds. A catalyst system for the preparation of cyclic carbonates by the fixation of carbon dioxide (CO₂) onto epoxides is presented. This system is designed for easy application due to the availability of the compounds on an industrial scale as well as moderate reaction conditions. Notably, it avoids the use of metal-halogen catalysts and instead employs a tertiary amine as the catalytic center, in conjunction with an alcohol acting as a hydrogen bond donor (HBD). The kinetics of the cycloaddition reaction between epoxides and CO₂ were thoroughly investigated using IR spectroscopy. Remarkably, optimization of the amino-to-alcohol group ratio and the amine structure was carried out to enhance the overall performance of the catalyst system showing a synergistic effect between the tertiary amine and the hydroxyl. Most notably, this entire process is conducted without the use of solvents and operates at ambient pressure, underscoring its significant ecological advantages.

固定二氧化碳是可持续合成化合物的一个关键问题。本文介绍了一种通过将二氧化碳 (CO2) 固定在环氧化物上制备环状碳酸盐的催化剂系统。该系统的设计易于应用，因为可以在工业规模上获得化合物，而且反应条件适中。值得注意的是，它避免了使用金属卤素催化剂，而是采用叔胺作为催化中心，同时使用醇作为氢键供体（HBD）。利用红外光谱对环氧化物与 CO2 的环化反应动力学进行了深入研究。值得注意的是，通过优化氨基与酒精基团的比例以及胺的结构，提高了催化剂系统的整体性能，显示了叔胺与羟基之间的协同效应。最值得注意的是，整个过程无需使用溶剂，并在环境压力下运行，这突出了其显著的生态优势。

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引用次数: 0

Three-component carbonylative Michael addition of aryl bromides using abundant metal-carbonyl under light 在光照下利用丰富的金属羰基对芳基溴进行三组分羰基迈克尔加成反应

Tetrahedron Green Chem

Pub Date : 2024-10-02 DOI: 10.1016/j.tgchem.2024.100056

Shiqian Zhang , Quansheng Mou , Bowen Cao, Tongyu Han, Mingxin Liu

Carbonyl compounds are widely found in various chemical reactions and natural products. Herein, a light-driven carbonylative cross-coupling reaction of bromobenzene was reported. Co₂(CO)₈ was used as an abundant solid carbonyl source to synthesize various Michael addition products with high yields. This reaction has broad substrates scope with good functional group tolerance. The mechanism study indicated that the reaction is achieved by the formation of benzoyl radical from homolytic C–Co cleavage under irradiation.

羰基化合物广泛存在于各种化学反应和天然产物中。本文报告了溴苯的光驱动羰基交叉偶联反应。以 Co2(CO)8 为丰富的固体羰基源，高产率地合成了多种迈克尔加成产物。该反应具有广泛的底物范围和良好的官能团耐受性。机理研究表明，该反应是在辐照下由同源 C-Co 裂解形成苯甲酰基而实现的。

引用次数: 0

Solvent-free microwave reactions towards significant organic transformations: A green approach 实现重大有机转化的无溶剂微波反应：绿色方法

Tetrahedron Green Chem

Pub Date : 2024-09-13 DOI: 10.1016/j.tgchem.2024.100054

Animesh Mondal , Chhanda Mukhopadhyay

The electromagnetic radiation from microwave irradiation has been widely employed as a heating source in various significant organic transformations over the past two decades. The method, without adding any solvent while tied to microwave treatment, is acompletely environmentally benign platform with conspicuous advancements and has resulted in copious advantages with regards to rate of reaction and yield of the products compared to the other classical techniques. Therefore, in this review, we have attempted to summarize some recently developed organic reactions based on microwave-radiated solvent-free protocols, which would be very efficient for academic and industrial use without affecting the principles of green chemistry.

过去二十年来，微波辐照产生的电磁辐射已被广泛用作各种重要有机转化的加热源。这种方法在微波处理过程中不添加任何溶剂，是一种完全无害环境的平台，具有显著的先进性，与其他传统技术相比，在反应速率和产物收率方面具有很大优势。因此，在这篇综述中，我们试图总结最近开发的一些基于微波辐射无溶剂方案的有机反应，这些反应在不影响绿色化学原理的前提下，在学术和工业应用方面都非常有效。

引用次数: 0

Egg shell powder mediated Cu catalyst: A biowaste based catalytic approach for the synthesis of quinazolin-4(3H)-ones and propargyl amines 蛋壳粉介导的铜催化剂：基于生物废料的喹唑啉-4(3H)-酮和丙炔胺合成催化方法

Tetrahedron Green Chem

Pub Date : 2024-09-11 DOI: 10.1016/j.tgchem.2024.100055

Nilakshi Dutta , Kaberi Hazarika , Roktopol Hazarika , Bulan B. Boruah , Surajit Konwer , Bipul Sarma , Diganta Sarma

A novel and efficient approach for a tandem oxidative synthesis of quinazolin-4(3H)-one from 2-aminobenzonitrile and benzyl alcohol has been unveiled via Cu₂(CO₃)(OH)₂. Herein CuSO_4.5H₂O accompanied by egg shell powder is used for the easy preparation of Cu₂(CO₃)(OH)₂. The reported method portrays a wide range of substrate scope with good to excellent yield and the given reaction proceed at room temperature within 12 h. Single crystal of one of the synthesized quinazolin-4(3H)-ones was analysed through single crystal X-ray diffraction (SC-XRD). Some of the compounds reported here are also known to possess various pharmaceutical activities. Eventually the newly prepared catalyst was applied for propargylamine synthesis via a multi component reaction. Perceiving all the advantages, present protocol is conceivably considered as clean, cost-effective and sustainable over reported procedures used for synthesis of quinazolin-4(3H)-ones and propargyl amines.

通过 Cu2(CO3)(OH)2，一种以 2-氨基苯甲腈和苯甲醇为原料串联氧化合成喹唑啉-4(3H)-酮的新型高效方法已经问世。在这里，CuSO4.5H2O 和蛋壳粉一起被用于轻松制备 Cu2(CO3)(OH)2。通过单晶 X 射线衍射 (SC-XRD) 分析了合成的一种喹唑啉-4(3H)-酮的单晶。报告中的一些化合物还具有多种药物活性。最终，新制备的催化剂被用于通过多组分反应合成丙炔胺。考虑到所有这些优点，可以认为本方案比已报道的用于合成喹唑啉-4(3H)-酮和丙炔胺的程序更加清洁、经济和可持续。

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引用次数: 0

Photocatalysed eosin Y mediated synthesis of biologically potent 4 (3H)-quinazolinone 光催化曙红 Y 介导的生物活性 4 (3H) - 喹唑啉酮的合成

Tetrahedron Green Chem

Pub Date : 2024-09-02 DOI: 10.1016/j.tgchem.2024.100053

Pravin Kumar Singh , Rohit Kumar , Vishal Srivastava , Praveen Pratap Singh

An environmentally benign green and metal-free visible light mediated approach for the synthesis of biologically potent 4(3H)-quinazolinone through multicomponent reaction of readily available starting materials potassium salt of anthranilic acid, aryl carboxylic acid, aliphatic/aromatic amine catalyzed by Eosin-Y has been developed with wide range of applications in pharmaceutical. Integrated process reduces the mechanical loss of the intermediate during the process of isolation.

在 Eosin-Y 催化下，通过易得的起始原料蒽酸钾盐、芳基羧酸、脂肪族/芳香族胺的多组分反应，开发出了一种绿色环保、无金属的可见光介导方法，用于合成具有生物药效的 4(3H)-喹唑啉酮，该方法在制药领域有着广泛的应用。一体化工艺减少了中间体在分离过程中的机械损失。

引用次数: 0

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Tetrahedron Green Chem

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