Article
Chemistry, Organic
Mandapati Bhargava Reddy, Kesavan Prasanth, Ramasamy Anandhan
Summary: A metal-free photoredox catalyzed process using proton-coupled electron transfer was developed for the controlled radical cyclization cascade of o-alkynylated benzamides. This reaction allows the addition of amidyl N-centered radical to C-C triple bond under mild conditions and the synthesis of 3-hydroxyisoindolin-1-ones and phthalimides. Additionally, a time tunable synthesis of 3-hydroxyisoindolin-1-ones and phthalimides via beta-carbonyl-C(sp(3)) bond cleavage was achieved under visible light irradiation.
Article
Chemistry, Multidisciplinary
Marek Moczulski, Ewelina Kowalska, Elzbieta Kusmierek, Lukasz Albrecht, Anna Albrecht
Summary: This study describes a doubly decarboxylative, photoredox synthesis method which successfully synthesized 4-substituted-chroman-2-ones and 2-substituted-chroman-4-ones. Key parameters include visible light, photoredox catalyst, base, anhydrous solvent, and inert atmosphere.
Article
Chemistry, Organic
Ji-Wang Fang, Fang-jie Liao, Yang Qian, Chao-Chen Dong, Li-Jin Xu, Han-Yuan Gong
Summary: Three-substituted 4H-quinolizin-4-ones were synthesized with good selectivity and high efficiency using a facile method based on alkyne substrate control. The reaction has a broad substrate scope (20 examples, up to 93% yield) and is easy to scale up. The strategy of alkyne substrate control could be further expanded for more complex structures.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Rayhane Hammami, Pascale Maldivi, Christian Philouze, Sebastien Carret, Benjamin Darses, Soufiane Touil, Jean-Francois Poisson
Summary: A variety of 4-phosphinylpyrrolidin-3-ones were synthesized via a [3+2] cycloaddition reaction between aryl aldonitrones and phosphinylallenes. The products were obtained as unique 4,5-trans diastereomers in yields ranging from 47% to 80% for 23 examples. Chiral racemic allenes exhibited a moderate 2:1 to 4:1 2,5-diastereoselectivity. Under the reaction conditions, the cycloadducts undergo a rearrangement to selectively afford the corresponding pyrrolidin-3-ones. DFT calculations provided insights into the mechanism involving the homolytic cleavage of the N-O bond of the cycloadduct.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Nikola Topolovcan, Filip Dupli, Matija Gredicak
Summary: A comprehensive study on the influence of N-substitution on the stereoselective outcome of the synthesis of 3-methyleneisoindolin-1-ones from 3-alkyl-3-hydroxyisoindolin-1-ones is reported. The results show that substrates without N-substituent exclusively afford the Z-isomer, while an increase in the size of the N-substituent leads to the formation of a stereoisomeric mixture with the E-isomer as the major component.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mingming Zhao, Yiming Guo, Qi Wang, Lanqi Liu, Shujie Zhang, Wei Guo, Lin-Ping Wu, Fayang G. Qiu
Summary: This paper presents an efficient synthesis of 2-iminothiazolidin-4-ones through a copper-catalyzed tandem annulation reaction involving alkyl amines, isothiocyanates, and diazo acetates. The [2 + 1 + 2] cyclization method offers advantages such as readily accessible starting materials, simplicity of operation, mild reaction conditions, high yields, step-economy, and tolerance towards diverse functional groups. Furthermore, the reaction is applicable to gram-scale synthesis and the preparation of bioactive molecules.
Article
Chemistry, Organic
Yu Nie, Jing Li, Jun Yan, Qianjia Yuan, Wanbin Zhang
Summary: An efficient iridium-catalyzed enantioselective hydrogenation method using iPr-BiphPHOX ligand for 2-alkylidene 1,4-benzoxazin-3-ones was reported, delivering reduced products with excellent yields (up to 99%) and enantioselectivities (up to 99% ee). The reaction worked well on a gram scale with low catalyst loadings and no erosion in enantioselectivity. Additionally, three bioactive molecules can be easily obtained from the reduced products.
Article
Chemistry, Applied
Nathan Trometer, Matthieu Roignant, Elisabeth Davioud-Charvet
Summary: Here, we report a safe and economical multigram synthesis of 6-fluoromenadione, which is an important intermediate in the synthesis of novel biologically active agents.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Organic
Jianwei Xie, Muhammad Suleman, Ke Zhang, Ping Lu, Yanguang Wang
Summary: In this study, an unexpected cascade ring expansion/annulation reaction was reported between 4-diazo-1,4-dihydroisoquinolin-3-ones and a variety of isatin derivatives in the presence of Sc(OTf)3 catalyst. Novel indolobenzazepinones were synthesized in good to excellent yields by excluding nitrogen and carbon dioxide gases. This method is characterized by high bond-forming efficiency, a novel reaction mechanism, readily available starting materials, commercially available cheap catalyst, broad substrate scope, and mild reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zhi-Lin Wu, Jin-Yang Chen, Xian-Zhi Tian, Wen-Tao Ouyang, Zhuo-Tao Zhang, Wei-Min He
Summary: A novel and efficient electro-chemical initiated radical strategy was developed for the preparation of both N-substituted and N-unsubstituted 4-selanylisoquinolin-1(2H)-ones through selenylation of isoquinolin-1(2H)-ones with organodiselenides under chemical oxidant-, additive-free and ambient conditions.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Organic
Byung Jun Park, Ji Sun Yang, Sung-Gon Kim
Summary: A novel method for synthesizing benzotriazepin-1-ones has been developed using a hexafluoroisopropanol-promoted decarboxylative cascade reaction. The key feature of this innovative reaction is the [4 + 3] annulation of hexafluoroisopropyl 2-aminobenzoates with in situ generated nitrile imines. This approach offers a simple and efficient way to synthesize a wide range of complex and highly functional benzotriazepinones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Jan Bojanowski, Anna Albrecht
Summary: A new doubly decarboxylative Michael-type addition method has been developed for the synthesis of biologically relevant compounds in good yields. The decarboxylative reaction pathway has been confirmed through mechanistic studies, and an attempt to develop an enantioselective variant of the cascade has also been described.
Article
Chemistry, Organic
Shunyao Li, Lanfei Zhang, Qian He, Xiaofei Zhang, Chunhao Yang
Summary: An efficient and mild synthetic approach for 2-alkyl-substituted chroman-4-ones via zinc-mediated cascade decarboxylative beta-alkylation and dechlorination of 3-chlorochromones was developed. This method employed commercially available starting materials and was performed under mild conditions, yielding moderate to excellent product yields. It could be utilized to construct a diverse library of derivatives for potential lead compound discovery in drug development.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Bhaskar B. Dhotare, Sahil Kumar, Amey Wadawale, Sandip K. Nayak, Mukesh Kumar, Dibakar Goswami
Summary: A novel metal-free approach for the synthesis of various 3-substituted-3-arylbenzofuran-2(3H)-ones has been developed via H2SO4-mediated dehydrative substitution, yielding moderate to good yields. Mechanistically, the substitution with the alkoxy group proceeds through a phenolic-hydroxyester intermediate, forming the desired product through cascade dehydration-relactonization steps.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Natalya Yu. Lisovenko, Ekaterina R. Nasibullina, Svetlana S. Kharitonova, Olga A. Myshkina
Summary: A convenient and facile approach was developed for the synthesis of functionalized 4-substituted compounds. The method is based on the regioselective synthesis of novel compounds containing a trichloromethyl group, followed by hydrolysis. The structures of these compounds were confirmed by single-crystal X-ray diffraction.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Physical
Ipek Munar, Volkan Findik, Isa Degirmenci, Viktorya Aviyente
JOURNAL OF PHYSICAL CHEMISTRY A
(2020)
Article
Polymer Science
Eyup Metin, Nergis Arsu, Saron Catak, Viktorya Aviyente
EUROPEAN POLYMER JOURNAL
(2020)
Article
Chemistry, Medicinal
Zeynep Pinar Haslak, Sabrina Zareb, Ilknur Dogan, Viktorya Aviyente, Gerald Monard
Summary: This study proposes a protocol based on the linear relationship between calculated atomic charges and experimental pK(a) values for accurate prediction of carboxylic acids' pK(a)'s. Through testing various methods, a specific combination was found to best reproduce experimental pK(a) values, and the stability of the protocol was verified through molecular dynamics simulations.
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2021)
Article
Biochemistry & Molecular Biology
Basak Koca Findik, Zeynep Pinar Haslak, Evrim Arslan, Viktorya Aviyente
Summary: The physicochemical properties of a drug molecule play a crucial role in determining the therapeutic effectiveness of the drug. This study involved quantum mechanical calculations to predict solvation free energy and transfer energy of drug-like compounds, achieving high accuracy and correlation in logP and pK(a) value predictions.
JOURNAL OF COMPUTER-AIDED MOLECULAR DESIGN
(2021)
Article
Acoustics
Asu Ziylan-Yavas, Nilsun H. Ince, Ece Ozon, Evrim Arslan, Viktorya Aviyente, Basak Savun-Hekimoglu, Aysen Erdincler
Summary: The study investigated the degradability of caffeine in water using different Advanced Oxidation Processes, finding that hybrid AOPs, particularly UV-H2O2/TiO2, were the most effective for caffeine removal. The addition of ultrasound increased the decomposition rate of caffeine but reduced the overall degradation rate.
ULTRASONICS SONOCHEMISTRY
(2021)
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
Esra N. Soysal, Volkan Findik, Burcu Dedeoglu, Viktorya Aviyente, Dean J. Tantillo
Summary: The energetic viability of the previously proposed biogenetic pathway for the formation of two unique monoterpenoid indole alkaloids, voacafricine A and B, was investigated. The results suggest that the previously suggested pathway is not energetically viable and an alternative biosynthetic precursor is likely.
Article
Chemistry, Medicinal
Evrim Arslan, Zeynep Pinar Haslak, Gerald Monard, Ilknur Dogan, Viktorya Aviyente
Summary: Drug molecules in solution can exist in ionized or nonionized states. Ionization is important for water solubility and drug-receptor interactions, while the nonionized form enhances lipid solubility, allowing the drug to cross cell membranes. This study proposes an accurate and computationally affordable method for predicting acetonitrile pKa values of thiazol-2-imine derivatives, using quantum mechanical approaches. Benchmark studies demonstrated high correlation between calculated pKa values and experimental values, using the isodesmic method at the M062X/6-31G** level of theory with SMD solvation model. Experimentally unknown pKa values for synthesized thiazol-2-imine structures are also proposed.
JOURNAL OF CHEMICAL INFORMATION AND MODELING
(2023)
Article
Engineering, Chemical
Idil I. Demiralp, Ipek Azizoglu, A. Barkin Cimen, Mert Haktanir, Seda Karahan, Zeynep Pinar Haslak, Viktorya Aviyente
Summary: Highly acidic crude oils are considered as good alternatives to typical crude oils for transportation fuels, but their corrosion poses a major concern. This study uses quantum mechanical tools to understand the unimolecular decomposition of carboxylic acids and naphthenic acids (NAs). The results reveal the effects of temperature and other factors on the decomposition process, which can help optimize the processes and provide reaction rates for kinetic models.
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
(2023)
Article
Chemistry, Organic
Semiha Kevser Bali, Zeynep Pinar Haslak, Gulsah Cifci, Viktorya Aviyente
Summary: The human topoisomerase IB enzyme relaxes supercoils on double-stranded DNA by forming a covalent DNA/hTopoIB complex. Inhibition of hTopoIB results in cell death, making it a potential target for cancer treatment. Different inhibitors, such as CPT and IQN, have shown different preferences for DNA bases when bound to the DNA/hTopoIB complex. This study investigates the affinities of CPT and an IQN derivative to different DNA base pairs, providing insights for designing gene-specific and more potent compounds to combat cancer through hTopoIB poisoning.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Basak Koca Findik, Umut Cilesiz, Semiha Kevser Bali, Canan Atilgan, Viktorya Aviyente, Burcu Dedeoglu
Summary: This study investigates the iron binding sites and release process of human serum transferrin using quantum chemical tools. The results show that protonation events and conformational changes play an important role in iron release. The release of iron in the N-lobe is thermodynamically favorable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Sule Erol Gunal, Ipek Azizoglu, Oya Arica, Zeynep Pinar Haslak, Viktorya Aviyente, Ilknur Dogan
Summary: This study successfully synthesized 5-benzyl-3-(o-aryl)-2-thiohydantoin and 5-isobutyl-3-(o-aryl)-2-thiohydantoin derivatives and analyzed and assigned their chiral isomers using techniques such as HPLC and H-1 NMR. The results showed that the chiral isomers of these derivatives existed in unequal amounts of SM, SP, RM, and RP stereoisomeric forms, with a high prevalence of the P isomers over the M isomers.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
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
Deniz Akgul, Samira F. Kurtoglu-oztulum, Yuxin Zhao, Volkan Findik, Antonio Monari, Alper Uzun, Viktorya Aviyente
Summary: Ionic liquids (ILs) have been used as ligands to modify the electronic structure and enhance the electron-donor/acceptor efficiency of metal-oxide supported Ir(CO)(2) complexes. The role of ILs in these interactions has been explained using Density Functional Theory.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2022)
Article
Chemistry, Physical
Volkan Findik, Basak Koca Findik, Viktorya Aviyente, Antonio Monari
Summary: In this study, the photophysical properties of three thiol derivatives commonly used as photoinitiators in thiol-ene free radical polymerization were investigated using time dependent density functional theory. The results revealed that the photolysis of S-H is achieved through triplet excited states, with alkyl thiol potentially generating photoinduced radical species in both the first excited singlet state and first triplet state. The research provides insights into the photoinitiator efficiency based on potential energy surface topologies and absorption intensity in the lowest energy region.
PHYSICAL CHEMISTRY CHEMICAL PHYSICS
(2021)
