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A Novel Baker’s Yeast-Mediated Microwave-Induced Reduction of Racemic 3-Keto-2-Azetidinones: Facile Entry to Optically Active Hydroxy β-Lactam Derivatives 新型贝克酵母介导的微波诱导还原外消旋3-酮-2-氮杂环丁酮:促进光学活性羟基β-内酰胺衍生物的进入
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2022-01-26 DOI: 10.2174/2213337209666220126123630
Aparna Das, R. N. Yadav, B. Banik
Microwave technology, together with enzymatic catalysis is a nature-friendly chemical synthesis method with low wastage of solvent and good yield of the products.Enzymes from various microorganisms can be used in the biochemical processes of a wide range of compounds assisted by microwave irradiationIn this work, the microwave-induced reaction of α-keto β-lactams by Baker's yeast in organic solvent was conducted to afford optically active cis and trans-α-hydroxy-β-lactams for the first time.These hydroxy compounds are the precursors of numerous natural products of medicinal significances.
微波技术与酶催化相结合是一种自然友好的化学合成方法,溶剂损耗低,产物收率高。来自各种微生物的酶在微波辐射的辅助下可用于多种化合物的生物化学过程。本工作中,贝克酵母在有机溶剂中对α-酮-β-内酰胺进行了微波诱导反应,首次获得了具有光学活性的顺式和反式-α-羟基-β-内酰胺。这些羟基化合物是许多具有药用意义的天然产物的前体。
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引用次数: 0
Polymer Supported Proline-Based Organocatalysts in Asymmetric Aldol Reactions: A Review 聚合物负载脯氨酸基有机催化剂在不对称醛醇反应中的研究进展
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2022-01-12 DOI: 10.2174/2213337209666220112094231
Rubina Shajahan, Rithwik Sarang, Anas Saithalavi
The use of proline-based organocatalysts has acquired significant importance in organic synthesis, especially in enantioselective synthesis. Proline and its derivatives are proven to be quite effective chiral organocatalysts for a variety of transformations including the aldol reaction, which is considered as one of the important C-C bond forming reactions in organic synthesis. The use of chiral organocatalysts has several advantages over its metal-mediated analogues. Subsequently, a large number of highly efficient proline-based organocatalysts including polymer-supported chiral analogues have been identified for aldol reaction. The use of polymer-supported organocatalysts exhibited remarkable stability under the reaction conditions and offered the best results particularly in terms of its recyclability and reusability. These potential benefits along with its economic and green chemistry advantages have led to the search for many polymer-supported proline catalysts. In this review, recent developments in exploring various polymer immobilized proline-based chiral organocatalysts for asymmetric aldol reactions are described.
脯氨酸基有机催化剂的使用在有机合成,特别是对映选择性合成中具有重要意义。脯氨酸及其衍生物被证明是一种非常有效的手性有机催化剂,可用于多种转化,包括醛醇反应,醛醇反应被认为是有机合成中重要的C-C键形成反应之一。使用手性有机催化剂与其金属介导的类似物相比有几个优点。随后,大量高效的脯氨酸基有机催化剂(包括聚合物负载的手性类似物)被确定用于醛醇反应。使用聚合物负载的有机催化剂在反应条件下表现出显著的稳定性,并提供了最好的结果,特别是在其可回收性和可重用性方面。这些潜在的好处以及它的经济和绿色化学优势已经导致了许多聚合物负载的脯氨酸催化剂的研究。本文综述了用于不对称醛醇反应的基于脯氨酸的聚合物固定化手性有机催化剂的研究进展。
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引用次数: 3
Agro-waste sourced catalyst as an eco-friendly and sustainable approach for Knoevenagel condensation reaction 农业废弃物来源催化剂作为环保和可持续的方法为Knoevenagel缩合反应
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2021-12-22 DOI: 10.2174/2213337209666211222145453
Krishnappa B Badiger, S. Khatavi, P. B. Hiremath, Kantharaju Kamanna
The present work describes an eco-friendly and sustainable approach for the Knoevenagel condensation of an aromatic aldehyde with ethyl cyanoacetate, and salicylaldehyde with Meldrum acid for the synthesis of ethyl benzylidenecyanoacetate and 3-carboxy coumarin (2-oxo-2H-1-benzopyran) derivatives, respectively. The reaction performed under greener catalytic media Water Extract of Watermelon Fruit Peel Ash (WEWFPA) is an eco-friendly protocol derived from the agro-waste feedstock. Various protocols have been reported for the synthesis of Knoevenagel condensation reaction using a hazardous catalyst or/and solvent found toxic to the environment, reaction time longer, poor yield, and required purification of the final product. The present method provides several added advantages of being completely greener, economic, giving high yield, inexpensive catalyst, and the final product isolated in pure form with good yield. The objective of the study was to develop a green methodology for the synthesis of ethyl benzylidenecyanoacetate and 3-carboxy coumarin derivatives.The agro-waste based catalyst developed avoids the use of external inorganic/organic base, additives, and solvent-free synthesis of Knoevenagel condensation of ethyl benzylidenecyanoacetate and 3-carboxy coumarin derivatives under rt and microwave irradiation, respectively described. The microwave irradiation condition requires less time for the completion of the reaction and also gave better yield isolationWe have demonstrated WEWFPA as a greener homogenous agro-waste is employed under rt stirring and microwave irradiation for the economic synthesis of ethyl benzylidenecyanoacetate and 3-carboxy coumarin derivatives. The developed method was found robust, non-hazardous and solvent-free with simple work-up gave target product.In conclusion, we have established an efficient, simple, agro-waste based catalytic approach for the synthesis of ethylbenzylidenecyanoacetate and 3-carboxy coumarin derivatives employing WEWFPA as an efficient catalyst under rt stirring and microwave synthesis, respectively. The method is a greener, economical and eco-friendly approach for the synthesis of Knoevenagel condensation products. The advantages of the present approach are solvent-free, no external metal, chemical base free, short reaction time and isolated product in good to excellent yields. The catalyst is agro-waste derived, which has abundant in natural sources, thus making the present approach a greener one.
本工作描述了一种环保和可持续的方法,芳香族醛与氰乙酸乙酯缩合,水杨醛与梅尔德鲁姆酸缩合,分别合成了苯基苄基氰乙酸乙酯和3-羧基香豆素(2-氧- 2h -1-苯并吡喃)衍生物。在绿色催化介质西瓜果皮灰水提物(WEWFPA)下进行的反应是一种源自农业废物原料的环保方案。已经报道了各种方案,用于合成Knoevenagel缩合反应,使用有害的催化剂或/和溶剂,发现对环境有毒,反应时间长,收率低,并且需要对最终产物进行纯化。本方法具有完全绿色环保、经济、产率高、催化剂价格低廉、最终产物分离纯度高、产率高等优点。本研究的目的是建立一种绿色的方法来合成乙酸乙酯和3-羧基香豆素衍生物。所开发的基于农业废弃物的催化剂避免了使用外部无机/有机碱、添加剂,并在rt和微波辐照下分别无溶剂合成了Knoevenagel缩合的苄基异氰乙酸乙酯和3-羧基香豆素衍生物。微波辐照条件下,完成反应所需时间更短,产率也更高。我们已经证明,WEWFPA作为一种更环保的均质农业废弃物,在rt搅拌和微波辐照下,用于经济地合成乙酸乙酯和3-羧基香豆素衍生物。结果表明,该方法稳定、无毒、无溶剂,处理简单,可得到目标产物。综上所述,我们建立了一种高效、简单、基于农业废弃物的催化方法,利用WEWFPA作为高效催化剂,分别在rt搅拌和微波合成下合成了乙基苄基异氰乙酸酯和3-羧基香豆素衍生物。该方法是一种绿色、经济、环保的合成Knoevenagel缩合产物的方法。该方法的优点是无溶剂、无外部金属、无化学碱、反应时间短、分离产物收率高。催化剂来源于农业废弃物,具有丰富的自然资源,因此使目前的方法更加环保。
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引用次数: 2
Green Multi-Component Synthesis of Fused heterocyclic derivatives: An atom economic ecofriendly approach for complex molecules 融合杂环衍生物的绿色多组分合成:复杂分子的原子经济环保方法
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2021-12-21 DOI: 10.2174/2213337209666211221162019
R. Dhanalakshmi, Gopal Jeya, M. Anbarasu, V. Sivamurugan
The construction of fused heterocyclic compounds is always fascinating on the strength of their applications as novel pharmaceuticals. Multi-component reactions (MCRs) are atom economical, beneficial, straightforward and ecofriendly approach for synthesis of complex heterocycles in a single step with higher selectivity.The review mainly focused on the synthesis of fused heterocycles such as pyrimidine - chromene, Pyrrolo - pyrazine, Pyrazolo - pyrimidine, pyran - imidazole and pyrazole- imidazole - pyrimidine, pyran - pyridmidone, pyrrolo - chromene, pyridine-pyrimidinone, fused indole derivatives, furano - pyran along with some simple MCRs discussed, which published in in the period of 2019 and 2020. A table of summary about 50 heterocycles with product, catalysts and cited literature for are given at end.From this review we understand that MCRs can deliver an effortless access to molecular targets of our interest with wide choice of reactants and their combinations. Thus, the creativity and choice of reactants are pushing the development in MCRs towards more atom economical and eco-friendly approachUnderstanding recent trends in the development of MCRs is a requisite for anyone, who wish to synthesise simple and fused heterocycles. By keeping this as primary objective, the present review provides an overview of latest developments in fused heterocyclic synthesis via green multicomponent reactions in the period of 2019 and 2020.
融合杂环化合物的构建由于其作为新型药物的应用而一直备受关注。多组分反应是一种原子经济、有利、简单、环保的一步合成复杂杂环化合物的方法,具有较高的选择性。主要综述了嘧啶-铬、吡咯-吡嗪、吡唑-嘧啶、吡喃-咪唑、吡唑-咪唑-嘧啶、吡喃-吡啶酮、吡咯-铬、吡啶-嘧啶酮、熔融吲哚衍生物、呋喃-吡喃等融合杂环的合成,并讨论了一些简单的mcr,发表于2019年和2020年。最后给出了50种杂环化合物及其产物、催化剂和相关文献的综述。从这篇综述中我们了解到,mcr可以通过广泛的反应物及其组合选择,轻松地获得我们感兴趣的分子靶标。因此,反应物的创造性和选择正在推动mcr的发展,使其朝着更加原子经济和环保的方向发展。对于任何希望合成简单和融合杂环的人来说,了解mcr发展的最新趋势是必要的。以此为主要目标,本文综述了2019 - 2020年绿色多组分反应融合杂环合成的最新进展。
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引用次数: 0
One-pot access to 2-oxazolines via a Castro-Stephens coupling and intramolecular cyclization Castro-Stephens偶联和分子内环化一锅法合成2-恶唑啉
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2021-12-13 DOI: 10.2174/2213337208666211213141836
D. Nighot, A. Jain, Imran Ali, Varun Rawat
Here, we have reported easy one-pot access to a series of oxazolines using a modified Castro-Stephens coupling protocol. 2-oxazolines have been shown to have significant biological activity and wide-ranging applications in organic chemistry. These properties make oxazolines as heterocyclic compounds of immense importance. The objective of this study is to synthesize oxazoline derivatives via an economical and one-pot protocol. 2-oxazoline has been synthesized through Cu-powder mediated Castro-Stephens coupling and intramolecular cyclization route. The mechanism involves a rearrangement in which one of the oxygen from the N-acylamino alcohol group is liberated as water and then transferred to alkyne functionality to form 2-oxazoline derivatives. The oxazolines were characterized by NMR, mass, and XRD studies. The protocol is economically viable and uses readily available Cu-powder along with DMF for cross-coupling and cyclization steps.
在这里,我们报道了使用改进的Castro-Stephens耦合协议轻松地一锅获取一系列恶唑啉。2-恶唑啉在有机化学中具有重要的生物活性和广泛的应用。这些性质使得恶唑啉作为杂环化合物具有极大的重要性。本研究的目的是通过经济和一锅法合成恶唑啉衍生物。通过铜粉介导的Castro-Stephens偶联和分子内环化途径合成了2-恶唑啉。其机理包括一个重排,其中n -酰基氨基醇的一个氧被释放为水,然后转移到炔官能团形成2-恶唑啉衍生物。通过核磁共振、质量和x射线衍射对所合成的恶唑啉进行了表征。该方案在经济上可行,并使用现成的铜粉和DMF进行交叉偶联和环化步骤。
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引用次数: 0
Editorial 编辑
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2021-12-01 DOI: 10.2174/221333720803211109103525
B. Banik
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引用次数: 0
The Effect of Dicarboxylic Acid Catalyst Structure on Hydrolysis of Cellulose Model Compound D-Cellobiose in Water 二羧酸催化剂结构对纤维素模型化合物d -纤维素二糖在水中水解的影响
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2021-11-29 DOI: 10.2174/2213337208666211129090444
Harshica Fernando, A. Amarasekara
Polycarboxylic acids are of interest as simple mimics for cellulase enzyme catalyzed depolymerization of cellulose. In this study, DFT calculations were used to investigate the effect of structure on dicarboxylic acid organo-catalyzed hydrolysis of cellulose model compound D-cellobiose to D-glucose. Binding energy of the complex formed between D-cellobiose and acid (Ebind), as well as glycosidic oxygen to dicarboxylic acid closest acidic H distance were studied as key parameters affecting the turn over frequency of hydrolysis in water. α-D-cellobiose - dicarboxylic acid catalyst down face approach showed high Ebind values for five of the six acids studied; indicating the favorability of down face approach. Maleic, cis-1,2-cyclohexane dicarboxylic, and phthalic acids with the highest catalytic activities showed glycosidic oxygen to dicarboxylic acid acidic H distances 3.5-3.6 Å in the preferred configuration. The high catalytic activities of these acids may be due to the rigid structure, where acid groups are held in a fixed geometry.
聚羧酸是纤维素酶催化纤维素解聚的简单模拟物。在本研究中,采用DFT计算研究了结构对二羧酸有机催化纤维素模型化合物d -纤维素二糖水解为d -葡萄糖的影响。研究了d -纤维素二糖与酸(Ebind)形成的配合物结合能,以及糖苷氧与二羧酸最接近的酸性H距离作为影响水解翻转频率的关键参数。α- d -纤维二糖-二羧酸催化剂下表面法对所研究的6种酸中的5种具有较高的Ebind值;表明正面向下的方法是有利的。催化活性最高的马来酸、顺式-1,2-环己烷二羧酸和邻苯二甲酸在优选构型中表现为糖苷氧到二羧酸的酸性H距离为3.5 ~ 3.6 Å。这些酸的高催化活性可能是由于刚性结构,其中酸基团保持在固定的几何形状。
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引用次数: 1
Liquid Membranes in Catalysis 催化中的液膜
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2021-11-18 DOI: 10.2174/2213337208666211118104716
M. Ashraf, M. Mir
The supported ionic liquid (SIL) membranes have demonstrated huge potential for numerous applications in current separation science and catalysis. Membrane technology allows for separation of complex mixtures of gases, vapours, liquids and /or solids below trivial conditions. Simultaneous chemical transformations can also be achieved in membranes by using catalytically active materials comprising the membrane or embedded catalysts in the custom built membrane reactors. In the present editorial, the remarkable contribution of liquid membranes in catalysis is highlighted. Some recent applications are presented and compared with conventional methods. In addition, SILs and their applications in catalysis, catalytic membranes and recent advances in membrane separation processes are briefly described.
负载离子液体(SIL)膜在当前的分离科学和催化中显示出巨大的应用潜力。膜技术允许在简单的条件下分离复杂的气体、蒸汽、液体和/或固体混合物。在定制的膜反应器中,通过使用含有膜或嵌入催化剂的催化活性材料,也可以在膜中实现同时的化学转化。在这篇社论中,强调了液体膜在催化中的显著贡献。介绍了该方法的一些最新应用,并与传统方法进行了比较。此外,还简要介绍了SILs及其在催化、催化膜和膜分离过程中的应用。
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引用次数: 0
Synthesis, Characterization and Biochemical Analysis of Azo-metal complex of Embelin with Second Group Transition Metals 含第二族过渡金属的偶氮金属配合物的合成、表征及生化分析
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2021-11-02 DOI: 10.2174/2213337208666211102104240
M. Mir, M. Ashraf
The objective of the work is to synthesize, characterize and biochemically analyze Azo-metal complex of Embelin with Second Group Transition Metals.The genus Embelia is a well-known herb and has considerable importance in the field of pharmaceutical chemistry. The plant species has been used considerably as a traditional medicine in Ayurveda, old Chinese medicine, and Siddha for a long time. The dried berries of this plant, called “vidanga” have boundless biochemical properties, like anthelmintic, carminative, antibacterial, antibiotic, and hypoglycemic.Embelin, metal-embelin (EM) and azo-metal-embelin (EAM) complexes were synthesized, analysed for antioxidant and antimicrobial properties. The metal-embelin (EM) complexes and metal-azo-embelin (EAM) complexes were synthesized by pure mixing of embelin, azo-embelin and metals viz, Tc, Ru, Rh, Pd, Ag and Cd. The embelin and EAN complexes were analysed by various spectroscopic techniques, viz, UV-visible, FTIR, NMR, TGA, MS and CHNS analysis.The results authenticate the reaction between metals, and bidentate embelin occurs via quinonic and enolic oxygen atoms as [M (Emb) 2 (H2O)] 2H2O and [M (Emb-Azo)2 (H2O)2]. The antioxidant results show that the complexation between metals and compounds decreases the antioxidant potential significantly. In contrast, the antimicrobial activity shows that cobalt and nickel embelin complexes showed more than 74% growth inhibition against the concerned microbes in comparison to embelin alone. As the results are taken into consideration, the scavenging property of embelin shows the reduction in power upon complexation with metals and azo-metals. Also, embelin and its associates as metal-embelin and metal-azo-embelin can be used as antioxidant and antimicrobial agents significantly.
本工作的目的是合成、表征和生化分析Embelin与第二族过渡金属的偶氮金属络合物。Embelina属是一种著名的草本植物,在药物化学领域具有相当重要的地位。长期以来,这种植物在阿育吠陀、老中医和悉达教中被大量用作传统药物。这种被称为“维丹加”的植物的干浆果具有无限的生化特性,如驱虫、胭脂虫、抗菌、抗生素和降血糖。合成了Embelin、金属Embelin(EM)和偶氮金属Embeline(EAM)复合物,并对其抗氧化和抗菌性能进行了分析。通过将embelin、偶氮embelin与金属Tc、Ru、Rh、Pd、Ag和Cd的纯混合,合成了金属embelin(EM)配合物和金属偶氮embelin(EAM)配合物。结果证实了金属和双齿embelin之间的反应是通过醌氧原子和烯醇氧原子[M(Emb)2(H2O)]2H2O和[M](Emb-Azo)2)2]发生的。抗氧化结果表明,金属与化合物的络合作用显著降低了抗氧化能力。相反,抗菌活性表明,与单独的embelin相比,钴和镍embelin复合物对相关微生物的生长抑制率超过74%。考虑到这些结果,embelin的清除性能显示出与金属和偶氮金属络合时的功率降低。此外,embelin及其作为金属embelin和金属偶氮embelin的缔合物可显著用作抗氧化剂和抗菌剂。
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引用次数: 1
Green and Sustainable Technology: Efficient Strategy for Synthesis of Biologically Active Pyrimidine Derivatives 绿色与可持续技术:生物活性嘧啶衍生物合成的高效策略
IF 1.1 Q4 CHEMISTRY, PHYSICAL Pub Date : 2021-10-06 DOI: 10.2174/2213337208666211006143134
B. Sahoo, B. R. Kumar, Krishna Chandra Panda, J. Sruti, A. Tiwari, S. Patra
Green chemistry is also referred as sustainable technology which involves the design, synthesis, processing and use of chemical substances by reducing or eliminating the chemical hazards. This strategy focuses on atom economy, use of safer solvents or chemicals, use of raw materials from renewable resources, consumption of energy and decomposition of the chemical substances to non-toxic material which are eco-friendly. So, this technology is utilized for the sustainable development of novel heterocyclic scaffold like pyrimidine derivatives. Pyrimidine is a six membered heterocyclic aromatic compound with two nitrogen atoms at positions 1 and 3 in the ring system. Among the other heterocyclic compounds, pyrimidine derivatives plays major role due to their diverse promising biological activities such as antimicrobial, antifungal, anti-viral, anti-tubercular, anti-diabetic, anti-hypertensive, anticancer, anthelmintic, antioxidant, anti-epileptic, antipsychotic, anti-anxiety, antimalarial, antihistaminic, anti-parkinsonian, analgesic and anti-inflammatory etc. The various green methods used for synthesis of pyrimidine derivatives include microwave assisted synthesis, ultrasound induced synthesis, ball milling technique, grinding technique, photo-catalysis. These processes enhance the rate of the reaction which leads to high selectivity with improved product yields as compared to the conventional synthetic methods. This review is focused on the green synthesis of biologically active pyrimidine derivatives.
绿色化学也被称为可持续发展的技术,它涉及化学物质的设计、合成、加工和使用,以减少或消除化学危害。这一战略的重点是原子经济、使用更安全的溶剂或化学品、使用来自可再生资源的原材料、消耗能源和将化学物质分解为无害环境的无毒材料。因此,该技术可用于新型杂环支架如嘧啶衍生物的可持续开发。嘧啶是一种六元杂环芳香族化合物,在环系的1号和3号位置上有两个氮原子。在杂环类化合物中,嘧啶衍生物具有抗菌、抗真菌、抗病毒、抗结核、抗糖尿病、抗高血压、抗癌、驱虫药、抗氧化、抗癫痫、抗精神病、抗焦虑、抗疟疾、抗组胺、抗帕金森病、镇痛和抗炎等多种生物活性,具有重要作用。用于合成嘧啶衍生物的各种绿色方法包括微波辅助合成、超声诱导合成、球磨技术、研磨技术、光催化等。与传统的合成方法相比,这些方法提高了反应的速度,从而提高了产品收率和高选择性。本文对具有生物活性的嘧啶衍生物的绿色合成进行了综述。
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引用次数: 0
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Current Organocatalysis
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