Article
Chemistry, Multidisciplinary
Tien Tan Bui, Hee-Kwon Kim
Summary: A practical one-pot synthesis of ketones from primary alcohols was successfully performed using dibromoisocyanuric acid and various aromatic compounds in the presence of Fe2O3. This method provides an efficient and useful approach to synthesize aromatic ketones from primary alcohols under mild reaction conditions, yielding high amounts of products.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
Letian Zhang, Jiajun He, Jiabin Shen, Hao Xu, Dancheng Zhu, Chao Shen
Summary: A one-pot stepwise Ce(III)/photoassisted cross-dehydrogenative coupling/fluorooxidation process was developed to efficiently construct C3-heteroaryl 3-fluorooxindoles. This method utilized readily available chemical feedstocks and did not require the use of precious metals, oxidants, or additives. The products were obtained in moderate-to-good yields through recrystallization with favorable functional group compatibility. Additionally, this methodology successfully established C-C, C=O, and C-F bonds in a single step, providing a direct transformation of C=C bonds to functionalized C-C bonds.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Fatemeh Karimi, Behnaz Tighsazzadeh, Beheshteh Asadi, Iraj Mohammadpoor-Baltork, Mahsa Layeghi, Valiollah Mirkhani, Shahram Tangestaninejad, Majid Moghadam
Summary: An efficient and reusable catalyst has been synthesized and demonstrated high catalytic activity in the synthesis of multicomponent products under solvent-free conditions. The structure of the catalyst has been confirmed through various characterization techniques, and it has shown excellent recyclability in testing. The catalyst's recyclability, high product yield, short reaction time, and clean reaction profile make it promising for potential applications.
Article
Chemistry, Organic
Kazumasa Tanimoto, Hayaki Okai, Marina Oka, Ryoma Ohkado, Hiroki Iida
Summary: The aerobic oxidative cross-coupling of indoles with azoles is developed using flavin-iodine-coupled organocatalysis for the green synthesis of 2-(azol-1-yl)indoles. The one-pot three-component synthesis of 2-azolyl-3-thioindoles is achieved in an atom-economical manner by utilizing molecular oxygen as the only sacrificial reagent.
Article
Chemistry, Applied
Li-Na Dong, Ya-Meng Wang, Wan-Lu Zhang, Li-Ping Mo, Zhan-Hui Zhang
Summary: This study reports the synthesis and characterization of a novel magnetic biochar supported nickel catalyst for heterogeneous catalysis. The prepared catalyst exhibited excellent catalytic activity and reusability for the synthesis of spirooxindole-dihydropyridines derivatives.
APPLIED ORGANOMETALLIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mohammad Pirbaba, Rezvan Kardooni, Ali Reza Kiasat, Mohammad Sabaeian
Summary: Solar radiation-assisted green approach was developed for the chemoselective synthesis of 3-alkylated indoles via Yonemitsu-type condensation under catalyst-free conditions. The desired products were formed by one-pot three-component reaction using non-volatile solvent and renewable energy resources. The approach showed good scope and generality, and increased economic and environmental effectiveness.
ARABIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Applied
Thuy T. T. Ngo, Eric Besson, Emily Bloch, Sandrine Bourrelly, Richard Llewellyn, Stephane Gastaldi, Philip L. Llewellyn, Didier Gigmes, Trang N. T. Phan
Summary: A new approach for polymer functionalization of ordered mesoporous silicas (OMS) was demonstrated by cocondensation of silica precursor and a functional polymer, using a tailored amphiphilic copolymer as pore template. The novel strategy allows for incorporation of the functional polymer into the mesoporous silica, resulting in materials with high specific surface area and large pores, and acceptable CO2 adsorption capacity with selectivity towards CH4 and N2.
MICROPOROUS AND MESOPOROUS MATERIALS
(2021)
Article
Chemistry, Multidisciplinary
Jurgen Pahl, Emily Noone, Marina Uzelac, Kang Yuan, Michael J. Ingleson
Summary: In this research, a new diboron compound, Pyrazabole (1), was discovered, which can be transformed into ditopic electrophiles. The unique B center dot center dot center dot B separation in 1 enables double E-H functionalization of indoles and indolines. Specifically, the activation of 1 with HNTf2 generates an electrophile that can convert N-H indoles and indolines into N/C7-diborylated indolines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yue-Xiao Wu, Ming-Hui Huang, Kang Peng, Zhen Shi, Er-jun Hao, Zhi-Bing Dong
Summary: An iodine-catalyzed one-pot synthesis of benzoazole-substituted thioenamines was reported. The reaction proceeds through an electrophilic substitution pathway in a cross dehydrogenation coupling manner. The protocol is metal-free, easy to perform, tolerates various functional groups, and provides good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ganesh Karan, Samrat Sahu, Modhu Sudan Maji
Summary: This study reported a method for synthesizing only benzene ring-functionalized indoles and poly-substituted carbazoles in a one-pot fashion. By using different allylboronic acids, a wide range of substitution patterns were achieved, which was a challenging task. The scalable synthetic protocol allows for further modifications and was successfully applied to the synthesis of carbazole-based natural products glycozoline and glycozolinol.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
James L. Collins, Daryl Staveness, Madison J. Sowden, Corey R. J. Stephenson
Summary: This article details the development of a photochemical reaction involving cyclopropylimines and substituted alkenes, which undergo a [3+2] cycloaddition to form aminocyclopentane derivatives. The use of a Schiff base enables a masked N-centered radical approach, which is activated upon excitation with visible light. The cycloaddition products can be directly converted to N-functionalized aminocyclopentanes through solvolysis and N-acylation. The photochemical component of this reaction has been demonstrated to be feasible in continuous flow.
Article
Chemistry, Applied
Yu-Ri Lee, Xuan Huy Do, Seung Sang Hwang, Kyung-Youl Baek
Summary: A bifunctional zeolitic imidazolate framework catalyst with amine and sulfonic acid groups was successfully prepared through a simple two-step post-synthetic modification, showing good catalytic performance and reusability in the reaction.
Article
Engineering, Environmental
Armin Rezayan, Renfeng Nie, Jianshe Wang, Tianliang Lu, Chunbao Charles Xu, Yongsheng Zhang
Summary: This study presents an alternative approach to the selective transformation of cellulose into 5-hydroxymethylfurfural (HMF) without external catalysts. By functionalizing microcrystalline cellulose (MCC) through milling and oxidation pretreatment, a high yield of HMF was achieved under moderate reaction conditions. The study highlights the importance of MCC's characteristics and reaction conditions for HMF synthesis, offering a greener route to produce HMF from cellulose without acid/base catalysts.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Organic
Michal Urban, Martin Nigrini, Ivana Cisarova, Jan Vesely
Summary: The atom-economic method developed using a chiral amine-squaramide Mannich reaction and Au(I)-catalyzed hydroamination can efficiently prepare novel bispirocyclic compounds containing three fused heterocyclic scaffolds. This synthetic strategy, whether performed stepwise or as a one-pot process, enables the formation of chiral bispirocyclic [oxindole-pyrrolidine-pyrazolones] with high yields (up to 75%) and excellent enantioselectivities (up to 99%).
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Wei Wu, Beibei Luo, Yi You, Zhiqiang Weng
Summary: A novel synthesis approach for the construction of 2-trifluoroethyl-substituted benzofurans under copper-catalyzed conditions has been developed, with moderate to excellent yields (up to 93%). This method is also applicable to the formation of 2-trifluoroethylated indoles.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Biochemistry & Molecular Biology
Jose Clerigue, M. Teresa Ramos, J. Carlos Menendez
Summary: Mechanochemical conditions were utilized for the aza-vinylogous Povarov reaction, resulting in faster reactions with comparable yields to conventional methods. The reaction yielded 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro-1,5-naphthyridines functionalized at C-2, C-4 and C-6 positions.
Review
Biochemistry & Molecular Biology
J. Carlos Menendez
Summary: The treatment of COVID-19 requires pharmacological intervention targeting both the viral infection and inflammatory stages. Antiviral drugs can target viral proteins and host proteins, with the latter having the advantage of being effective against all variants of the virus. In addition, drugs targeting the hyperinflammatory phase of the disease, such as JAK kinases inhibitors and anti-inflammatory corticosteroids, are also important strategies.
Review
Chemistry, Organic
Jose Clerigue, M. Teresa Ramos, J. Carlos Menendez
Summary: Catalytic asymmetric Povarov protocols have experienced explosive growth in the past decade, focusing on the use of chiral Lewis and Bronsted acids, as well as strategies involving hydrogen bond formation and covalent aminocatalysis. Recent variations, such as the nitroso Povarov reaction and interrupted Povarov reactions, are also discussed as alternative routes to chiral scaffolds beyond tetrahydroquinolines.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Angel Cores, Noelia Carmona-Zafra, Olmo Martin-Camara, Juan Domingo Sanchez, Pablo Duarte, Mercedes Villacampa, Paloma Bermejo-Bescos, Sagrario Martin-Aragon, Rafael Leon, J. Carlos Menendez
Summary: Curcumin analogues with the fragment of piperlongumine showed broad-spectrum activity in the treatment of Alzheimer's disease, with good absorption, antioxidant properties, and the ability to inhibit inflammation.
Article
Biochemistry & Molecular Biology
Angel Cores, Patrycja Michalska, Jose Miguel Perez, Enrique Crisman, Clara Gomez, Mercedes Villacampa, Jose Carlos Menendez, Rafael Leon
Summary: This study synthesized hybrids combining the antioxidant and NRF2 induction properties of lipoic acid with the neuroprotective activity of CGP37157. The compounds showed a good neuroprotective profile against oxidative stress and hyperphosphorylation, as well as significant anti-neuroinflammatory activity.
Article
Chemistry, Analytical
Victor Gonzalez-Ruiz, Angel Cores, M. Mar Caja, Vellaisamy Sridharan, Mercedes Villacampa, M. Antonia Martin, Ana Olives, J. Carlos Menendez
Summary: The fluorescence properties and anion-binding response of newly synthesised carbazole derivatives were studied, and potential anion sensors were designed. 1-hydroxycarbazole proved to be a sensitive fluorescent sensor for fluoride and chloride anions through hydrogen bond interactions.
Article
Chemistry, Organic
Giammarco Tenti, Jose Clerigue, M. Teresa Ramos, J. Carlos Menendez
Summary: A five-step route to synthesizing a ring-contracted analogue of the oxicam derivative propoxicam from thiosalicylic acid, sarcosine, and N,N-dimethyl-1,3-propanediamine is described. Key steps include the base-promoted cross-Claisen coupling reaction, installation of a beta-ketoamide moiety, and a Hg(II)-induced cyclization.
Article
Biochemistry & Molecular Biology
Lucia Perez-Regidor, Joan Guzman-Caldentey, Nils Oberhauser, Carmen Punzon, Balazs Balogh, Jose R. Pedro, Eva Falomir, Alessandra Nurisso, Peter Matyus, J. Carlos Menendez, Belen de Andres, Manuel Fresno, Sonsoles Martin-Santamaria
Summary: In this study, a computer-aided drug repurposing approach was used to virtually screen and discover novel TLR4 modulators with a non-lipopolysaccharide-like structure. After screening thousands of approved drugs and drug-like molecules, several compounds with TLR4 antagonist activity were identified through biological assays. This collaborative work expands the chemical diversity for the inspiration of new classes of TLR4 modulators.
Article
Chemistry, Organic
Miriam Ruiz-Serrano, Pilar Lopez-Alvarado, J. Carlos Menendez
Summary: Researchers found that the reaction between an a-formylcyclohexanone derivative and tosyl azide, in the presence of rhodium trifluoroacetate dimer, produced an acylsulfonamide derivative. This transformation is proposed to occur through a domino mechanism involving the in situ generation of an a-diazoketone, which is then transformed into a rhodium carbenoid and combined with N-tosylformamide, a side product of the first step. Overall, this transformation results in the formation of a C-N bond between the formyl carbon and the azide nitrogen adjacent to the sulfonyl group.
Article
Chemistry, Organic
Angel Cores, Mercedes Villacampa, J. Carlos Menendez
Summary: The microwave-assisted reaction of 2-nitroimidazole with 3-bromophenacyl bromide in the presence of potassium carbonate as a base and dimethylformamide as a solvent afforded 2-(3-bromophenyl)imidazo[2,1-b]oxazole. The formation of this compound was explained via a domino mechanism comprising an initial N-alkylation reaction of the imidazole substrate, followed by the base-promoted deprotonation of the position adjacent to the carbonyl to give an enolate anion that finally cyclizes via an intramolecular SNAr reaction, with the loss of the nitro group as potassium nitrite. Then, the proposed 1-(3-bromophenacyl)-2-nitroimidazole intermediate could be isolated by reducing the reaction time and was shown to be a precursor of the imidazo[2,1-b]oxazole final product.
Review
Chemistry, Medicinal
Alvaro Sarabia-Vallejo, Pilar Lopez-Alvarado, J. Carlos Menendez
Summary: Alzheimer's Disease (AD) is a challenging health issue, particularly in developed countries, due to increasing prevalence and economic burden. Previous efforts to discover new diagnostic and therapeutic tools have failed, highlighting the need for new approaches. Theranostic agents have emerged as promising tools for AD research and personalized medicine, providing diagnostic information and therapeutic activity simultaneously. This review emphasizes the positive impact that theranostics can have in the future clinical practice.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Diksha Rajput, Gowsia Jan, Muthu Karuppasamy, Nattamai Bhuvanesh, Subbiah Nagarajan, C. Uma Maheswari, J. Carlos Menendez, Vellaisamy Sridharan
Summary: An efficient cascade annulation reaction using secondary amine catalyst was developed for the synthesis of functionalized 2H-chromenes and 1,2-dihydroquinolines with a p-quinone methide scaffold. The microwave-assisted strategy achieved high yields and completion of reactions in just 15 min. The synthesized products were further transformed into valuable compounds via a palladium-catalyzed double C-H bond activation process and epoxidation.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Damiano Rocchi, Juan F. Gonzalez, Olmo Martin-Camara, Maria Grazia Perrone, Morena Miciaccia, Antonio Scilimati, Celine Decouty-Perez, Esther Parada, Javier Egea, J. Carlos Menendez
Summary: This study found that m-terphenylamine derivatives are selective inhibitors of cyclooxygenase-1 (COX-1), able to block microglia inflammatory response and elicit a neuroprotective effect.
Review
Pharmacology & Pharmacy
Alvaro Sarabia-Vallejo, Maria del Mar Caja, Ana I. Olives, M. Antonia Martin, J. Carlos Menendez
Summary: Many active pharmaceutical ingredients have low oral bioavailability due to factors such as poor solubility and physical and chemical instability. The formation of inclusion complexes with cyclodextrins can improve the oral bioavailability of many drugs. The microencapsulation process can modify key properties of the included drugs. Examples of stabilizing labile drugs and increasing the bioavailability of class IV drugs through inclusion complex formation are discussed. The stabilization and improvement in nutraceuticals used as food supplements is also considered. Cyclodextrin-based nanofibers lead to significant bioavailability enhancements. The synthesis of chemically modified cyclodextrins, polymers, and nanosponges based on cyclodextrins is discussed, as well as analytical techniques for characterizing inclusion complexes.
Review
Biochemistry & Molecular Biology
Angel Cores, Noelia Carmona-Zafra, Jose Clerigue, Mercedes Villacampa, J. Carlos Menendez
Summary: Quinones can be both cytoprotective and cytotoxic in the treatment of neurodegenerative diseases due to their modification of biomolecules. Low doses of electrophilic quinones activate the Keap1/Nrf2 pathway and induce the expression of detoxifying enzymes. Natural quinones like coenzyme Q(10) and its analogues have neuroprotective effects relevant to Alzheimer's and Parkinson's diseases. Other endogenous and non-endogenous quinones with neuroprotective activities are also discussed.
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
