Article
Biochemistry & Molecular Biology
Lingamurthy Macha, Ranjith Jala, Sang-Yun Na, Hyun-Joon Ha
Summary: This article presents a method for synthesizing multi-substituted pyrroles, which involves regiospecific ring-opening of aziridine followed by intramolecular cyclization with a carbonyl group. The protocol is highly atom economical and can be applied to the synthesis of various pyrroles, including natural products.
Article
Chemistry, Multidisciplinary
Zheng Long, Wang Lijia, Tang Yong
Summary: In(NTf2)(3) was found to be a powerful Lewis acid catalyst for the intramolecular nucleophilic ring-opening reaction of donor-acceptor cyclopropane with indole. This method enables the facile construction of pyrrolo[1,2-alpha]-indole framework structure under mild reaction conditions.
ACTA CHIMICA SINICA
(2022)
Article
Chemistry, Organic
Angel Ho, Austin Pounder, Samuel Koh, Matthew P. Macleod, Emily Carlson, William Tam
Summary: This study demonstrates the ability of carboxylic acid tethered CPOBD to undergo ring-opening reactions under mild acidic conditions, with high regioselectivity towards type 3 ring-opened products. Substitution at specific positions of CPOBD was found to hinder the ring-opening reactions and decrease the yields of ring-opened products. Overall, this work represents the first examples of acid-catalyzed intramolecular ring-opening reactions of CPOBD with carboxylic acid nucleophiles.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Nikhil Srivastava, Hyun-Joon Ha
Summary: Aziridine displays different regioselective ring-opening reactions depending on the functional group of its alkyl substituents. This reaction can efficiently generate various substituted heterocycles.
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Physical
Brett Baker, Christopher J. Cockram, Swar Dakein, Jonathan M. DeMaria, David M. George, Kaycie R. Malyk, Mormie Joseph F. Sarno, Allan Jay P. Cardenas
Summary: Ionic liquids are liquid salts composed of bulky molecular ions with melting points generally below 100 degrees C. Subtle changes in the structure of the anilinium cations greatly affect the physical properties of the organic salts, with pi-pi ring interaction playing a significant role in their melting points.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Review
Chemistry, Medicinal
Guillaume Masson, Domingo Gomez Pardo, Janine Cossy
Summary: This microreview focuses on the nucleophilic ring-opening of azetidiniums with various substitution patterns at C2, C3, and C4. The reactions often exhibit stereoselectivity and regioselectivity, leading to functionalized linear amines. Experimental selectivities correlated with Density Functional Theory (DFT) calculations provide insights into the factors governing regioselectivity.
Article
Chemistry, Organic
Xiu-Mei Kan, Jie Zhu, Pin-Hua Li, Zhi-Chuan Wu, Pei-Jun Yang
Summary: An efficient synthesis of g-amino ethers was achieved by Cu(OTf)2-catalyzed ring-opening of 2-aryl N-tosylazetidines with phenols. This reaction exhibited excellent yields and regio-selectivities, low catalyst loading, mild reaction conditions, and good scalability. One product was transformed into the drug molecule (+/-)-fluoxetine via a two-step procedure.
Article
Biochemistry & Molecular Biology
Jieun Choi, Taehwan Yu, Hyun-Joon Ha
Summary: The highly strained three-membered aziridine ring was activated as an aziridinium ion through alkylation of the ring nitrogen and subsequent ring opening with external nucleophiles. This method provides an easy route for synthesizing various N-alkylated amine-containing molecules with the introduction of external nucleophiles at either the alpha or beta position.
Article
Polymer Science
Huining Ding, Xianmin Wu, Bing Han, Ning Liu, Binyuan Liu, Il Kim
Summary: Highly regioselective ring-opening copolymerizations of 5-norbornene-2,3-dicarboxylic anhydride (NA) and epoxide monomers have been achieved using Cr-III catalysts and specific ligands, allowing for the control of cis/trans regioselectivity in the resulting polyesters by adjusting feed ratio and monomer structure. The resulting polyesters from the copolymerization of NA and epichlorohydrin provide a robust platform for post-modification, with the ring-strained C=C double bonds in the norbornene units facilitating further functionalization through azide-alkene 1,3-dipolar cycloaddition reactions based on desired targets.
Article
Chemistry, Organic
Petr Oeser, Tereza Edlova, Marek Cubinak, Tomas Tobrman
Summary: This study describes the preparation of halohydrins from 2-halocyclobutanones via reactions with Grignard reagents at -78 degrees C, with the discovery of thermal ring-opening reaction of the prepared cyclobutanols leading to different products depending on the starting structure. The ring-opening mechanism for cyclobutanols was proposed based on the experimental outcomes.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zhen Yu, Meng Wang, Xu-Man Chen, Shuai Huang, Hong Yang
Summary: The novel macrobicyclic olefin system shows good selectivity and high stereoselectivity in ROMP, with sacrificial cleavage of the silyloxide bridge providing clean-structured, non-auxiliaried polymers.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Medicinal
Guoyun Bai, Thomas N. O'Connell, Michael A. Brodney, Christopher R. Butler, Lara C. Czabaniuk, Adam M. Gilbert, Erik A. LaChapelle, Chao Li, Laura A. McAllister, Kevin Ogilvie, Laurence Philippe, Romelia Salomon-Ferrer, Michael J. Shapiro, Jeremy T. Starr, Daniel P. Uccello, Jane M. Withka, Jiangli Yan, Matthew F. Brown
Summary: The presence of ring strain in azetidines can cause stability issues, but a series of N-RN substituted azetidines have been described in this study that undergo an acid-mediated intramolecular ring-opening decomposition via nucleophilic attack. Research was conducted to understand the mechanism of decomposition, allowing for the design of stable analogs.
ACS MEDICINAL CHEMISTRY LETTERS
(2021)
Review
Chemistry, Organic
Kristaps Leskovskis, Janis Mikelis Zakis, Irina Novosjolova, Maris Turks
Summary: Ring opening of purines can lead to the preparation of ring-modified purine derivatives, which are privileged molecular scaffolds in medicinal and agricultural chemistry. This approach is a useful alternative for their synthesis and can compete well with other methods.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hector Soria-Carrera, Isabel Franco-Castillo, Pilar Romero, Santiago Martin, Jesus M. de la Fuente, Scott G. Mitchell, Rafael Martin-Rapun
Summary: The innovative On-POM polymerization strategy combines inorganic scaffolds with amino acids, allowing the synthesis of hybrid materials with additive or synergistic properties, such as bactericidal poly(lysine)-POM hybrids. This versatile method provides a flexible approach for tailoring and enhancing the specificity and performance of hybrid antimicrobial materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Jun Dong, Wei Chang, Youwei Chen, Xingcai Huang
Summary: A series of 2,4-dithiohydantoins were synthesized efficiently by regioselective reactions of phenacyl sulfoxides bearing 1-methyl-1H-tetrazole and N-substituted thioureas. The proposed mechanism involves the generation of alpha-sulfines, carbonphilic attack of sulfines by substituted thioureas, and dehydration condensation. This method provides a safe strategy for the preparation of 2,4-dithiohydantoins.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Dylan Dagoneau, Amandine Kolleth, Pierre Quinodoz, Gamze Tanriver, Saron Catak, Alexandre Lumbroso, Sarah Sulzer-Mosse, Alain De Mesmaeker
HELVETICA CHIMICA ACTA
(2020)
Article
Chemistry, Organic
Gamze Tanriver, Dylan Dagoneau, Ulfet Karadeniz, Amandine Kolleth, Alexandre Lumbroso, Sarah Sulzer-Mosse, Alain De Mesmaeker, Saron Catak
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Polymer Science
Elias Van Den Broeck, Bart Verbraeken, Karen Dedecker, Pieter Cnudde, Louis Vanduyfhuys, Toon Verstraelen, Kristof Van Hecke, Valentin Victor Jerca, Saron Catak, Richard Hoogenboom, Veronique Van Speybroeck
Article
Polymer Science
Eyup Metin, Nergis Arsu, Saron Catak, Viktorya Aviyente
EUROPEAN POLYMER JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Dylan Dagoneau, Amandine Kolleth, Pierre Quinodoz, Beyza Horoz, Saron Catak, Alexandre Lumbroso, Sarah Sulzer-Mosse, Alain De Mesmaeker
Summary: This study describes an effective method for the synthesis of highly substituted cyclobutanones with excellent diastereoselectivity, involving a [2+2] cycloaddition reaction and isomerization of cyclobutaniminium salt.
HELVETICA CHIMICA ACTA
(2021)
Article
Chemistry, Physical
Jorick Franceus, Jolien Lormans, Lore Cools, Matthias D'hooghe, Tom Desmet
Summary: The study demonstrates significant phosphorylase activity can be established in GH3 glycoside hydrolases through single-site substitutions and further optimized through mutational paths. These findings suggest new insights into developing phosphorylases and provide a novel approach for future research in this field.
Article
Chemistry, Multidisciplinary
Dylan Dagoneau, Pierre Quinodoz, Amandine Kolleth, Mert Bozoflu, Beyza Horoz, Saron Catak, Philippe-Alexandre Poisson, Alexandre Lumbroso, Sarah Sulzer-Mosse, Alain De Mesmaeker
Summary: In this study, a straightforward 3-step synthesis of pyrrolizidinone derivatives with high overall yield was described. The method involves a sequential [2+2] cycloaddition, rearrangement, and S(N)2 reaction, allowing for a diverse range of pyrrolizidinone synthesis.
HELVETICA CHIMICA ACTA
(2022)
Article
Chemistry, Medicinal
Gamze Tanriver, Gerald Monard, Saron Catak
Summary: This study explored the conformational changes induced by deamidation in Bcl-x(L) using microsecond-long molecular dynamics simulations. The results showed significant changes in the motion and interaction patterns of the intrinsically disordered region (IDR) upon deamidation. Principal component analysis (PCA) revealed differences between wild-type and deamidated Bcl-x(L) and suggested that deamidation impacts the structure and dynamics of Bcl-x(L). Clustering analysis, H-bond analysis, and PCA highlighted alterations in conformation, interaction, and dynamics upon deamidation, indicating deamidation-induced allosteric effects.
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2022)
Article
Chemistry, Physical
Ekin Esme Bas, Pelin Ulukan, Antonio Monari, Viktorya Aviyente, Saron Catak
Summary: In this computational study, the researchers investigated TADF and non-TADF chromophores with benzophenone or its derivatives as the acceptor core and various donor moieties. They computed several excited state properties and utilized them, along with other descriptors, to study the potential TADF efficiency. The results showed that their descriptors and computational methodologies can effectively predict experimental results and provide guidance for future research on benzophenone-based TADF emitters.
JOURNAL OF PHYSICAL CHEMISTRY A
(2022)
Article
Chemistry, Multidisciplinary
Pierre Quinodoz, Amandine Kolleth, Dylan Dagoneau, Masahiko Yoshimura, Lucia Reyes Mendez, Mylene Joigneaux, Roman Staiger, Robin Horber, Sarah Sulzer-Mosse, Aybike Bekar Cesaretli, Ulfet Karadeniz Yezer, Saron Catak, Alain De Mesmaeker
Summary: This article describes a high yielding and metal-free method for synthesizing 9-aminophenanthrene derivatives and heterocyclic analogues. The conversion of the starting materials into keteniminium salts triggers a spontaneous electrocyclization reaction at room temperature within minutes. Density functional theory calculations and competition reactions were performed to explain the observed reactivity and understand the relative kinetics compared to other known reactions involving keteniminium salts.
HELVETICA CHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Pierre Quinodoz, Alexandre Lumbroso, Mathilde Lachia, Claudio Screpanti, Stefano Rendine, Beyza Horoz, Mert Bozoflu, Saron Catak, Raymonde Fonne-Pfister, Katrin Hermann, Alain De Mesmaeker
Summary: A new class of signaling molecules called strigolactams has been discovered, showing strong potential to induce the germination of the parasitic weed O. cumana and displaying enhanced chemical and soil stability. The stereoselective synthesis of these strigolactams has been achieved, which highlights the significant influence of stereochemistry on compound activity. Stability studies in soil reveal that stereoisomers have different degradation kinetics, emphasizing the importance of stereochemistry.
HELVETICA CHIMICA ACTA
(2023)
Article
Chemistry, Multidisciplinary
Masahiko Yoshimura, Pierre Quinodoz, Lucia Reyes Mendez, Amandine Kolleth, Sarah Sulzer-Mosse, Thomas Vent-Schmidt, Ulfet Karadeniz Yezer, Saron Catak, Alain De Mesmaeker
Summary: Polycyclic aromatic hydrocarbons (PAHs) are important molecules in science and technology. Amino-substituted PAHs have potential for use in materials science. However, current synthetic methods limit the diversity of amino-substituted PAH structures.
HELVETICA CHIMICA ACTA
(2023)
Article
Chemistry, Physical
Aslihan Hepguler, Pelin Ulukan, Saron Catak
Summary: In this study, the thermally activated delayed fluorescence (TADF) properties of emitters with sulfone-based acceptor moieties were investigated using density functional theory (DFT) methods. The focus was on three important structural parameters that affect the efficiency of intersystem crossing (ISC) and reverse intersystem crossing (RISC).
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2023)
Article
Chemistry, Physical
Pelin Ulukan, Ekin Esme Bas, Rengin Busra Ozek, Cansul Dal Kaynak, Antonio Monari, Viktorya Aviyente, Saron Catak
Summary: This study investigates the influence of electron-donating and electron-accepting groups and geometric factors on TADF emitters, providing a computationally effective protocol to assess TADF efficiencies.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Physical
Busenur Aslanoglu, Ilya Yakavets, Vladimir Zorin, Henri-Pierre Lassalle, Francesca Ingrosso, Antonio Monari, Saron Catak
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2020)