Article
Chemistry, Organic
Anirban Bera, Sk Abulkalam Azad, Prasanta Patra, Nayim Sepay, Rathin Jana, Tapas Das, Amit Saha, Shubhankar Samanta
Summary: Here, a weak acid-promoted tandem aza-Michael-aldol strategy has been presented for the synthesis of diversely fused pyrrolo[1,2-a]quinoline. The protocol allows for the construction of both pyrrole and quinoline ring in one pot, forming two C-N bonds and one C-C bond under transition-metal-free conditions. A ketorolac drug analogue and a tricyclic pyrrolo[1,2-a]quinoline fluorophore were successfully synthesized, with the latter being used to detect picric acid via fluorescence quenching.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Emma Campbell, Andrea Taladriz-Sender, Olivia Paisley, Alan R. Kennedy, Jacob T. Bush, Glenn A. Burley
Summary: This paper describes a modular approach to prepare tri- and tetracyclic carbazoles via sequential [3 + 2] heteroannulation. The optimization of Pd-catalyzed Buchwald-Hartwig amination followed by C/N-arylation in a one-pot process is established. Mechanistic analyses have identified the origins of the chemo- and regioselective sequential control of both bond-forming steps. The substrate scope is demonstrated by the preparation of a range of tri- and tetracyclic carbazoles, including expedient access to several natural products and anti-cancer agents.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Polymer Science
Guifu Si, Meizhou Qi, Chen Tan, Changle Chen
Summary: The paper introduces a tandem catalysis concept where a single catalyst enables multiple catalytic transformations to efficiently prepare novel polymers with various properties.
Article
Multidisciplinary Sciences
Prakash T. Parvatkar, Eugene S. Smotkin, Roman Manetsch
Summary: The synthesis of tetracyclic indole alkaloid (+/-)-decursivine was achieved through a tandem oxidative cyclization catalyzed by BINOL-phosphoric acid, using (bis(trifluoroacetoxy)iodo)benzene (PIFA) as an oxidizing agent. This represents a short and high-yielding route for the synthesis of (+/-)-decursivine from readily available starting materials.
SCIENTIFIC REPORTS
(2021)
Article
Chemistry, Multidisciplinary
Huanqin Guan, Mengqi Shen, Cooro Harris, Honghong Lin, Kecheng Wei, Michael Morales, Noah Bronowich, Shouheng Sun
Summary: This study reports the synthesis of Cu2O nanoparticles by controlling the oxidation of Cu nanoparticles, and investigates their application as catalysts in ammonia borane dehydrogenation, nitroarene hydrogenation, and amine/aldehyde condensation reactions. The 13 nm Cu2O nanoparticles show high catalytic activity in converting nitro groups to amines, and facilitate the synthesis of highly stable PBO materials.
Article
Chemistry, Organic
Pengyan Wang, Junhan Chen, Weigang He, Jiacheng Song, Hengqian Song, Hongbo Wei, Weiqing Xie
Summary: A concise asymmetric synthesis of (divided by)-isostrychnine is achieved through nine longest-linear steps with a 16% overall yield. Key features include catalytic asymmetric tandem double Michael addition, intramolecular dehydrative condensation/lactamization reaction, and allylic diazene rearrangement.
Article
Chemistry, Multidisciplinary
Zhi Chen, Yu-Fan Li, Shun-Zhong Tan, Qin Ouyang, Zhi-Chao Chen, Wei Du, Ying-Chun Chen
Summary: Herein, a palladium-catalysed multiple auto-tandem reaction for the efficient synthesis of formal pyrrolylmethylated amine products was reported. The regiodivergent selectivity could be switched by tuning the catalytic conditions. In addition, remote chirality transfer was achieved using an achiral ligand.
Article
Chemistry, Organic
Yetong Zhang, Lepeng Chen, Yinlin Shao, Fangjun Zhang, Zhongyan Chen, Ningning Lv, Jiuxi Chen, Renhao Li
Summary: The study presents a three-component tandem reaction allowing the synthesis of polysubstitution quinolines using 2-aminobenzonitriles, arylboronic acids, and ketones. This method is practical, efficient, and delivers functional quinolines with moderate to good yields and high functional group tolerance. Additionally, a new method for introducing halogen substituents into the target products has been developed, showing potential for further synthetic elaborations.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Physical
Qiang Chao, Tianlu Li, Ji-Xiang Jia, Zijie Li, Peng Peng, Xiao-Dong Gao, Ning Wang
Summary: This study presents a convenient and efficient strategy for modifying glycans to obtain structurally defined oligosaccharides, which is crucial for investigating their function and biological roles. The strategy involves the use of immobilized enzymes to selectively modify glycans with terminal galactose or Sia-Gal residues, allowing the assembly of diverse sialyl-galactosylated glycans. The utility of this strategy is demonstrated by the construction of a panel of Core 2 O-GalNAc glycans.
Article
Chemistry, Applied
Mohammad Bagher Teimouri, Zahra Bozorgpour Savadjani, Morteza Shiri, Rahman Bikas, Soheila Naderi
Summary: A new class of quinone dyes, xanthoquinones, have been synthesized through a cycloaddition reaction, resulting in a specific structure of xanthone and quinone subunits.
Article
Chemistry, Organic
Philipp C. Roosen, Alexander S. Karns, Bryan D. Ellis, Christopher D. Vanderwal
Summary: This study provides a detailed account of the concise and highly stereoselective synthesis of (+)-7,20-diisocyanoadociane (DICA), a structurally complex isocyanoditerpene with potent antiplasmodial activity. The synthesis strategy involves the construction of unsaturated tricyclic precursors followed by stereocontrolled Birch reductions and a subsequent bay ring formation to generate the isocycloamphilectane core.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yuxiang Zhao, Yanren Zhu, Guolan Ma, Qi Wei, Shaoxiong Yang, Xiaoyu Zeng, Hongbin Zhang, Jingbo Chen
Summary: Strategically integrating functional group manipulation into the ring system construction resulted in a short, enantioselective, gram-scale total synthesis of (-)-zephyranthine. The concise route includes a catalytic Michael/Michael cascade, an 8-step one-pot operation, regioselective construction of a double bond, and asymmetric dihydroxylation. This synthesis is flexible and paves a potential path to a variety of cyclohexylamine-fused tricyclic or polycyclic alkaloids.
Article
Chemistry, Applied
Gabriele Lupidi, Alessandro Palmieri, Marino Petrini
Summary: A novel riboflavin-promoted reaction of primary nitroalkanes coupled with a nitroaldol reaction was discovered, enabling the synthesis of functionalized nitro alcohols under mild reaction conditions. However, secondary nitroalkanes were consumed under the reaction conditions without yielding the expected nitroaldol products.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Review
Chemistry, Multidisciplinary
Nengzhong Wang, Zugen Wu, Junjie Wang, Nisar Ullah, Yixin Lu
Summary: The past two decades have seen remarkable growth of asymmetric organocatalysis, serving as a powerful platform for producing chiral molecules. Ring structures are widely present in organic compounds, and strategic construction of ring motifs is crucial in natural product synthesis.
CHEMICAL SOCIETY REVIEWS
(2021)
Article
Chemistry, Organic
Marina Velado, Roberto Fernandez de la Pradilla, Alma Viso
Summary: The highly diastereoselective sulfa-Michael addition of thiolates to enantiopure 2-sulfinyl dienes leads to anti or syn 2-ene-1,4-hydroxy sulfides in good yields and selectivities dependent on the reaction conditions in a diastereodivergent process. Synthetic applications of these enantiopure hydroxy sulfides by subsequent sigmatropic rearrangements have been outlined.
Article
Chemistry, Applied
Joshua Humphreys, Ferdinando Malagreca, Paul Hume, William Lewis, E. Stephen Davies, Stephen P. Argent, David B. Amabilino
Summary: The study reports on a series of N-alkylated PyrDPP dyes and their properties in solution and in the solid state, showing that the nature of the chain affects the molecular packing and absorption spectra in the solid state, with different chain dyes exhibiting variations in charge transfer performance.
Article
Biochemistry & Molecular Biology
Michelle Cutajar, Robert A. Stockman, Susan Braovac, Calin Constantin Steindal, Angeliki Zisi, Stephen E. Harding
Summary: Butvar B-98 and PDMS-OH have been identified as effective consolidants for archaeological wood. They offer an alternative to aqueous-based consolidants as they are soluble in organic solvents. Extensive characterization studies have been conducted on these polymers to provide conservators with information about their physical properties.
Article
Polymer Science
Mariana d'Almeida Gameiro, Philippa L. Jacob, Kristoffer Kortsen, Thomas Ward, Vincenzo Taresco, Robert A. Stockman, Yonas Chebude, Steven M. Howdle
Summary: This study reports a green and efficient extraction method for triglyceride vernonia oil from Vernonia galamensis using supercritical carbon dioxide, and successfully synthesizes polymerisable monomers based on vernolic acid.
JOURNAL OF POLYMER SCIENCE
(2022)
Article
Multidisciplinary Sciences
Xin Wu, Patrick Wang, William Lewis, Yun-Bao Jiang, Philip A. Gale
Summary: This study investigates the quantification of anion binding within lipid bilayers using a fluorescent macrocycle with strong sulfate affinity. The authors discover that the determinants of anion binding in lipid bilayers differ from those in solution. These findings provide insights into the principles of anion binding within lipid bilayers and have implications for the design of functional molecular systems at biomembrane interfaces.
NATURE COMMUNICATIONS
(2022)
Article
Polymer Science
Rachel L. Atkinson, Matthew Elsmore, Sean Smith, Morgan Reynolds -Green, Paul D. Topham, Daniel T. W. Toolan, Matthew J. Derry, Olivia Monaghan, Vincenzo Taresco, Derek J. Irvine, Robert A. Stockman, Davide S. A. De Focatiis, Steven M. Howdle
Summary: We reported the synthesis of terpene-based monomers from beta-pinene, which can be used to produce polymers with high Tg values and well-defined structures. The synthesized materials showed promising properties as hard blocks in thermoplastic elastomers, and ABA triblock copolymers incorporating a renewable soft block were also successfully synthesized using a difunctional RAFT polymerization method. The initial phase separation behavior and adhesive properties of these copolymers were investigated, highlighting their potential as renewably sourced thermoplastic elastomers.
EUROPEAN POLYMER JOURNAL
(2022)
Article
Multidisciplinary Sciences
Michelle Cutajar, Fabricio Machado, Valentina Cuzzucoli Crucitti, Susan Braovac, Robert A. Stockman, Steven M. Howdle, Stephen E. Harding
Summary: The Oseberg Viking ship burial is an extensive collection of Viking wooden artefacts found in Norway. Due to previous treatment with alum, these artefacts are now in a degraded state. In order to prevent further deterioration, researchers have synthesized two hydroxylated polymers, TPA6 and TPA7, which have properties that make them suitable for wood consolidation. Characterization of these polymers shows their optimal molar mass, conformation, and hydroxylated nature, particularly TPA7, making it an interesting lead for further research.
SCIENTIFIC REPORTS
(2022)
Article
Biochemistry & Molecular Biology
Valentina Cuzzucoli Crucitti, Aleksandar Ilchev, Jonathan C. Moore, Harriet R. Fowler, Jean-Frederic Dubern, Olutoba Sanni, Xuan Xue, Bethany K. Husband, Adam A. Dundas, Sean Smith, Joni L. Wildman, Vincenzo Taresco, Paul Williams, Morgan R. Alexander, Steven M. Howdle, Ricky D. Wildman, Robert A. Stockman, Derek J. Irvine
Summary: This study utilized the alpha parameter, a molecular descriptor, to design terpene-based polymers resistant to biofilm formation by Pseudomonas aeruginosa. The potential biofilm resistance of terpene-derived monomers was predicted and ranked using the alpha parameter. The monomers from commercially available terpenes were polymerized and confirmed to have biofilm resistance properties. The scaled-up monomers were successfully printed and used to create bio-instructive microparticles. The observations in this study have significant potential to produce bio-resistant coatings, packaging materials, fibers, and medical devices.
Article
Chemistry, Physical
Eleanor R. Kearns, Jack K. Clegg, William Lewis, Ada Fang, Bun Chan, Deanna M. D'Alessandro
Summary: As complex materials are widely used in emerging technologies for environmental and energy applications, it is important to be able to quantify their stimuli-response behaviors. In this study, a double [2 + 2] photocyclization reaction in a photoactive material was utilized as a powerful platform to quantitatively investigate solid-state photocyclization kinetics. The results showed a maximum rate observed between 0 degrees C and 20 degrees C of approximately 0.172 s-1, providing the first example of quantification of photocyclization kinetics in a MOF. Density functional theory calculations supported a singlet reaction mechanism for the double [2 + 2] photocyclization.
CHEMISTRY OF MATERIALS
(2022)
Article
Polymer Science
Harriet R. Fowler, Dara M. O'Brien, Daniel J. Keddie, Cameron Alexander, Derek J. Irvine, Robert A. Stockman, Steven M. Howdle, Vincenzo Taresco
Summary: Polyols and polyacrylates are widely used in polymer synthesis and can be used as monomers, initiators, or building blocks. Finding bio-based/renewable sources for these compounds is crucial due to the increasing need to reduce dependency on fossil fuels. By functionalizing the alkene moieties of common terpenes through oxidation, the toolbox of bio-based diols and triols is expanded. These polyols can be easily converted into terpene-derived diacrylates under mild conditions. As demonstrated, these monomers can be used in aza-Michael polymerizations to form new (bio)degradable poly-beta-amino esters.
MACROMOLECULAR CHEMISTRY AND PHYSICS
(2023)
Article
Multidisciplinary Sciences
Michelle Cutajar, Susan Braovac, Robert A. Stockman, Steven M. Howdle, Stephen E. Harding
Summary: The evaluation of two terpene-derived polymers, TPA6 and TPA7, as consolidants for archaeological wood was conducted. The objective was to expand the non-aqueous treatment options for the highly degraded Oseberg collection. Both polymers successfully penetrated the wood specimens, with a higher concentration on the surface. They also increased the hardness of the specimen surfaces. It is suggested to increase the polymer concentration and soaking time to facilitate better penetration into the wood cores in future investigations.
SCIENTIFIC REPORTS
(2023)
Article
Chemistry, Multidisciplinary
Max Roemer, William Lewis
Summary: Copper nanostructures were obtained by reducing Cu(I) under mild conditions in ethanol/water using sodium-l-ascorbate and sodium azide in an amination reaction. When reacting the halobenzene substrate in the presence of a bulk carbon black support, clustered copper sub-micrometer particles (SMPs) and microparticles (MPs) were formed. The supported nanostructures were characterized and found to be active catalysts in the azide-alkyne cycloaddition (CuAAC). The catalytic competency of the particles was assessed and optimized conditions were used for the synthesis of triazole compounds.
Article
Chemistry, Inorganic & Nuclear
Roberto Nolla-Saltiel, Ana M. Geer, Helen R. Sharpe, Cameron D. Huke, Laurence J. Taylor, Thomas G. Linford-Wood, Ashleigh James, Jamie Allen, William Lewis, Alexander J. Blake, Jonathan Mcmaster, Deborah L. Kays
Summary: This study reports the synthesis of ruthenium complexes with phosphinocarboxamide ligands and their use in forming metallacycles through halide abstraction/deprotonation reactions. The coordination and structure of these complexes were studied using X-ray diffraction and NMR spectroscopy, revealing the presence of intramolecular hydrogen bonding and rotational isomers in solution.
Article
Chemistry, Inorganic & Nuclear
Andrew J. Valentine, Ana M. Geer, Toby J. Blundell, Will Tovey, Matthew J. Cliffe, E. Stephen Davies, Stephen P. Argent, William Lewis, Jonathan McMaster, Laurence J. Taylor, Daniel Reta, Deborah L. Kays
Summary: Five structurally related two-coordinate Fe(II) m-terphenyl complexes were studied, and it was found that changing the functionalization of the ligand can alter their magnetic function. Using more electron donating R groups can slow down the rate of magnetic relaxation.
DALTON TRANSACTIONS
(2022)
Article
Chemistry, Multidisciplinary
Hunter J. Windsor, William Lewis, Suzanne M. Neville, Samuel G. Duyker, Deanna M. D'Alessandro, Cameron J. Kepert
Summary: A 3D Hofmann-like metal-organic framework with a 2,1,3-benzothiadiazole-based pillaring ligand has been synthesized. The encapsulation of a polycyclic aromatic hydrocarbon, chrysene, within the pore structure enables a new pathway to multi-step spin crossover behavior, where the observed two-step spin transition is attributed to the presence of multiple site environments and local guest positional effects within the host lattice.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Xiaochen Fu, Matthew Sale, Bowen Ding, William Lewis, Debbie S. Silvester, Chris D. Ling, Deanna M. D'Alessandro
Summary: A new enzyme-free glucose sensor with robustness, accuracy, and high sensitivity was developed in this study. The sensor shows improvement in operational flexibility compared to traditional systems, with the additional advantage of low sample loadings.
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
