Article
Chemistry, Physical
Yong Li, Hao Li, Jun Wu, Xinyue Yang, Xiaohua Jia, Jin Yang, Dan Shao, Lei Feng, Sizhe Wang, Haojie Song
Summary: This article introduces a durable superhydrophobic photothermal coating that can rapidly melt ice through photothermal conversion and prevent contamination and refreezing through self-cleaning properties.
APPLIED SURFACE SCIENCE
(2022)
Article
Chemistry, Physical
Leman Alkan, Ozgur Alver, Stephen T. Astley, Eralp Kulan, Cemal Parlak
Summary: The tandem Knoevenagel-Michael addition of diethyl malonate to nitro-substituted benzaldehydes was found to proceed in a mild and convenient process. The H-1 NMR spectra of the products showed significant changes according to the position of the nitro group. Conformational analysis calculations confirmed the presence of a structure containing a mirror plane near the ground state in all cases. However, increased steric crowding in the meta and ortho substituted products resulted in decreased rotational freedom of the ethyl substituents. Molecular orbital calculations predicted a higher electrophilic reactivity of the ortho nitro substituted product, consistent with the observed increase in steric stress.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Organic
Ruiying Ma, Hongzhou Yang, Ling Ye, Qiang Yang, Zhichuan Shi, Zhigang Zhao, Xuefeng Li
Summary: A one-pot, two-step aza-Michael/Michael/Michael process has been developed for the diastereospecific construction of C6a,C10acis-hydrophenanthridines in a highly enantioselective manner (83-99% ee). The tricyclic products were obtained in 50-99% isolated yields, sequentially promoted by bifunctional squaramide and diamine in a one-pot operation. This doubly annulative protocol demonstrates the facile construction of complex polycyclic structures through the full utilization of available reaction sites in readily prepared precursors.
Article
Chemistry, Organic
Ilya P. Filippov, Mikhail S. Novikov, Alexander F. Khlebnikov, Nikolai V. Rostovskii
Summary: A novel strategy for the synthesis of 1-pyrrolines based on the formal [4 + 1] annulation reaction has been developed in this study. The one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization. This method shows good substrate tolerance and can be used to synthesize 1-pyrrolines containing an ester group at the C3 position.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Yangjin Kuang, Katsumi Maeda, Ryosuke Matsubara, Masahiko Hayashi
Summary: A one-pot synthesis of 3-substituted indoles from 2-(2-nitro-1-phenylethyl)cyclohexanone derivatives catalyzed by Pd/C is described. The starting materials can be easily prepared by the reaction of substituted ketones and nitroalkenes. The reaction involves the treatment of 2-(2-nitro-1-phenylethyl)cyclohexanone derivatives with H-2 as a hydrogen donor in the presence of 10 mol % Pd/C, followed by the exchange of H-2 with CH2=CH2 as a hydrogen acceptor to afford a variety of 3-substituted indoles in high yields. The formation of intermediate nitrones is crucial for the smooth progress of the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Lucimara L. Zachow, Mateus Mittersteiner, Estefania C. Aquino, Helio G. Bonacorso, Marcos A. P. Martins, Nilo Zanatta
Summary: This study revealed the highly selective reactivity of 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one towards primary aliphatic amines, leading to the synthesis of two types of compounds with high yields and structurally characterized through single crystal X-ray diffraction and 2D NMR experiments.
SYNTHESIS-STUTTGART
(2021)
Article
Multidisciplinary Sciences
Takahiro Terunuma, Yujiro Hayashi
Summary: In this work, the enantioselective total synthesis of (-)-quinine has been achieved in a pot-economical manner, using five reaction vessels. The synthesis involves a total of fifteen reactions, which are carried out in separate vessels, with high yields and excellent stereochemical selectivity.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Physical
Zhi-Ying Gong, Cheng-Li Yang, Dan Wang, Lang Huang, Zhi-Bing Dong
Summary: An efficient and convenient one-pot synthesis of benzoxazole/benzothiazole-substituted esters is achieved through a selective Michael addition reaction. This protocol offers high selectivity, good functional tolerance, mild conditions, and excellent yields, demonstrating its potential for the preparation of biologically and pharmaceutically active compounds.
Article
Chemistry, Organic
Dipak J. J. Dahatonde, Aritra Ghosh, Adilakshmi Vutla, Sanjay Batra
Summary: In this study, a regioselective one-pot synthesis of 1,4,5-trisubstituted pyrazoles was reported using Morita-Baylis-Hillman (MBH) acetates derived from aryl aldehydes and alkyl or aryl hydrazines in the presence of iodine under aerobic conditions. The reaction involved nucleophilic substitution, oxidation, intramolecular aza-Michael reaction, cyclization, and oxidative aromatization. The synthetic applications of the pyrazoles in various reactions were also demonstrated.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Crystallography
Ahmed T. A. Boraei, Matti Haukka, Manar Sopaih, Abdullah Mohammed Al-Majid, Saied M. Soliman, Assem Barakat, Ahmed A. M. Sarhan
Summary: A straightforward synthesis route for a new 4-phenyl-1,2,5,6-tetraazafluoranthen-3(2H)-one was reported. The structure and molecular packing of the compound were confirmed through X-ray analysis and NMR.
Article
Chemistry, Organic
Xiaojing Xu, Huan Luo, Jiayi Shen, Jing Chen, Jie Ye, Ze-Feng Xu, Chuan-Ying Li
Summary: Valuable piperidin-4-one derivatives were synthesized efficiently via an α-imino carbene-initiated cascade reaction, demonstrating excellent alkyl migration selectivity facilitated by 2-bromoethyl neighboring group participation. This protocol is characterized by high efficiency, excellent migrating selectivity, broad substrate scope, and convenient one-pot procedure, making it an effective tool for piperidine derivative synthesis. The migration-annulation reaction of α-imino carbene presents a powerful strategy for heterocycle construction.
Article
Chemistry, Organic
Pradeep Kumar, Deepanshi Saxena, Rahul Maitra, Sidharth Chopra, T. Narender
Summary: This study presents a simple and efficient method for the synthesis of thioethers by reacting indoles with p-quinone methides using thiourea as the sulfur source. The reaction proceeds through the formation of an S-(3-indolyl)isothiuronium iodide intermediate and subsequent generation of indolethiol, which attacks the 1,6 position of p-quinone methides. The desired thioethers are obtained in good to excellent yields.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Energy & Fuels
Qixiang Kang, Xinghua Zhang, Yanyan Cui, Xuelai Zhao, Wuyu Wang, Jiapeng Zhang, Qi Zhang, Longlong Ma
Summary: Cycloalkanes jet fuel derived from biomass is the perfect alternative to fossil fuel. The Mannich-Michael reaction of cyclopentanone and formaldehyde followed by hydrodeoxygenation (HDO) is a promising method for producing high-density jet fuel. The combination of pyrrolidine and acetic acid showed high catalytic activity in the one-pot Mannich-Michael reaction under mild conditions. By using the enamine catalytic pathway, a high yield of condensed products and conversion of cyclopentanone was achieved. The alkali-treated H beta 25-1 catalyst combined with Pd/C effectively catalyzed the hydrodeoxygenation of the condensed products, resulting in a high yield of dicyclopentylmethane with desirable density and heating value. This work provides a new route for producing high-density jet fuel from lignocellulosic compounds.
Article
Polymer Science
Aaron Priester, Jimmy Yeng, Krista Hilmas, Anthony J. Convertine
Summary: Polysorbate 80 (PS80) was reacted with 3-mercaptopropyl trimethoxysilane (SiSH) via a photoinitiated thiol-ene reaction to obtain thiol-functional nanoparticles. These nanoparticles have a high number of thiol residues per particle, allowing for easy modification of particle properties. When added to 3D printing resin, the thiol-functional nanoparticles significantly enhance the curing rate.
Article
Chemistry, Multidisciplinary
Seiji Ogo, Takeshi Yatabe, Tamon Tome, Riko Takenaka, Yoshihito Shiota, Kenji Kato
Summary: This paper reports a method for the synthesis of H2O2 using a homogeneous catalyst in water, using only H2 and O2 without flammable mixtures or cocatalysts. The catalyst can remove electrons from H2, store them for the reduction of O2, and allow the protonation of the reduced oxygen to form H2O2. The turnover number (TON) is 910 under an H2/O2 (95/5) atmosphere (1.9 MPa) for 12 hours at 23 degrees C, which is the highest among any homogeneous catalysts. Furthermore, a reaction mechanism based on two crystal structures is proposed.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Biochemistry & Molecular Biology
Ursa Stanfel, Dejan Slapsak, Uros Groselj, Franc Pozgan, Bogdan Stefane, Jurij Svete
Summary: Silica gel-bound Cu(II)-enaminone complexes were prepared and showed promising catalytic activity in CuAIAC reactions, but suffered from poor reusability. Improved reusability was achieved by using a 4-aminobenzoic acid linker attached to the enaminone via an amide bond.
Article
Biochemistry & Molecular Biology
Selestina Gorgieva, Azra Osmic, Silvo Hribernik, Mojca Bozic, Jurij Svete, Viktor Hacker, Sigrid Wolf, Bostjan Genorio
Summary: In this research, a series of nanocomposite membranes based on chitosan and three different N-doped graphene derivatives were prepared and characterized, with the 0.07% loading of N-doped graphene derivatives significantly impacting the morphology and properties of the CS membrane. The CS/N rGONRs (0.07%) membrane showed improved performance in direct alkaline ethanol fuel cells compared to the pristine CS membrane.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Applied
Luka Ciber, Sebastijan Ricko, Jure Gregorc, Franc Pozgan, Jurij Svete, Helena Brodnik, Bogdan Stefane, Uros Groselj
Summary: This study demonstrates that Arylidene-Delta(2)-pyrrolin-4-ones can undergo organocatalyzed annulation with malononitrile to form dihydropyrano[3,2-b]pyrroles. The enantiomeric excess of the products can be increased by trituration. The enantioselectivity depends on the nature of the substrate and the conformation of the catalyst, which is solvent-controlled. The reaction mechanism involves a Michael addition reaction step followed by 6-exo-dig annulation, and the rate determining step is the former, consistent with the proposed model.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Applied
Nejc Petek, Bibi Erjavec, Dejan Slapsak, Aljaz Gaber, Uros Groselj, Franc Pozgan, Sebastijan Ricko, Bogdan Stefane, Marina Klemencic, Jurij Svete
Summary: A series of new fluorescent compounds were synthesized via copper-catalyzed reactions, exhibiting interesting and promising optical properties. Some of them were successfully used for protein labeling.
Article
Chemistry, Medicinal
Anze Meden, Damijan Knez, Xavier Brazzolotto, Florian Nachon, Jose Dias, Jurij Svete, Jure Stojan, Uros Groselj, Stanislav Gobec
Summary: The lead optimization of a series of tryptophan-based nanomolar BChE inhibitors resulted in highly potent, achiral, sp(3)-rich tertiary amines with better synthetic accessibility and high selectivity. Introduction of a carbamate warhead allowed conversion to pseudoirreversible inhibitors that covalently bound to BChE. The discovery of a novel leaving group chemotype and the structural analysis provided valuable insights for future optimization of this series.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Luka Vah, Tadej Medved, Uros Groselj, Marina Klemencic, Crtomir Podlipnik, Bogdan Stefane, Jernej Wagger, Marko Novinec, Jurij Svete
Summary: In silico evaluation showed that regioisomeric 5- and 3-hydroxy-substituted alkyl 1-aryl-1H-pyrazole-4-carboxylates have promising binding capability in the active site of dihydroorotate dehydrogenase of Plasmodium falciparum. Four ethyl 1-aryl-5-hydroxy-1H-pyrazole-4-carboxylates and their 3-hydroxy regioisomers were successfully prepared. Testing the compounds for their inhibition of PfDHODH revealed that some of them exhibited higher potency than a known inhibitor.
Article
Chemistry, Applied
Luka Ciber, Ana Gorenc, Misel Hozjan, Franc Pozgan, Jurij Svete, Helena Brodnik, Bogdan Stefane, Uros Groselj
Summary: This study reports the organocatalyzed Michael addition of N-substituted tetramic acids to nitroalkene acceptors followed by O-alkylation, yielding polyfunctionalized tetramic acids. The enantioselectivity of the product is influenced by the N-substituent of the substrate. Quantum chemical methods provide mechanistic insights into the transformation. The absolute configuration of the product is confirmed by single crystal structure analysis, which is consistent with the experimentally measured and calculated structures. Additionally, a comparative study of the alkylation of selected tetramic and tetronic acids with trans-beta-nitrostyrene is presented, showing the applicability of these compounds in dipeptide and depsipeptide sequences.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Polymer Science
Ursa Stanfel, Tomaz Kotnik, Sebastijan Ricko, Uros Groselj, Bogdan Stefane, Klemen Pirnat, Ema Zagar, Bostjan Genorio, Jurij Svete
Summary: New oligo- and polyenaminones with M-w around 7-50 KDa were synthesized using a transaminative amino-enaminone polymerization method. These polymers, which are insoluble in both water and organic solvents, possess film-forming properties, UV light absorption below 500 nm, and redox activity. These properties make them promising candidates for applications in optics, optoelectronics, and energy storage devices.
Article
Chemistry, Physical
Luka Ciber, Franc Pozgan, Helena Brodnik, Bogdan Stefane, Jurij Svete, Uros Groselj
Summary: A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and on enaminone or 1,2-benzenediamine as hydrogen bond donors were synthesized and evaluated for their organocatalytic activity in the Michael addition reaction. Enantioselectivities of up to 72% ee were observed.
Article
Biochemistry & Molecular Biology
Luka Ciber, Franc Pozgan, Helena Brodnik, Bogdan Stefane, Jurij Svete, Mario Waser, Uros Groselj
Summary: Ten novel bifunctional quaternary ammonium salt phase-transfer organocatalysts were synthesized and evaluated for their organocatalytic activity in electrophilic heterofunctionalizations and the Michael addition reaction. The reactions showed high conversion rates, but low enantioselectivities. The catalysts were fully characterized and the stereochemistry at the C-2 chiral center was determined.
Article
Chemistry, Multidisciplinary
Maya Chochkova, Almira Georgieva, Tsvetelina Ilieva, Madlena Andreeva, Georgi Pramatarov, Nejc Petek, Petranka Petrova, Martin Sticha, Yavor Mitrev, Jurij Svete
Summary: A series of cinnamic acid hybrids were synthesized and their antioxidant properties were evaluated. The hybrids containing a caffeoyl moiety and lipophilic adamantane core exhibited higher antioxidant activity, suggesting their potential benefits in pathological conditions associated with oxidative stress.
JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Misel Hozjan, Luka Ciber, Franc Pozgan, Jurij Svete, Bogdan Stefane, Uros Groselj
Summary: A study on the organocatalyzed synthesis of tert-butyl 2-amino-3-cyano-5-oxo-4-phenyl-5,7-dihydropyrano[2,3-c]pyrrole-6(4H)-carboxylate from Boc-tetramic acid and benzylidenemalononitrile was presented. Two bifunctional noncovalent organocatalysts were used, resulting in the racemic mixture of the product in both cases. The structure of the newly synthesized compound was confirmed by high resolution mass-spectrometry, H-1- and C-13-NMR, HSQC, and IR spectroscopy.
Article
Chemistry, Organic
Luka Ciber, Franc Pozgan, Jurij Svete, Bogdan Stefane, Uros Groselj
Summary: A three-step synthesis of 1-{(1S,2S,4R)-7,7-dimethyl-1-[(pyrrolidin-1-yl)methyl]bicyclo[2.2.1]heptan-2-yl}-1H-benzo[d]imidazole from camphor derived diamine was reported. The absolute configuration of the chiral center bearing the benzo[d]imidazole moiety was confirmed using NOESY. The newly synthesized compound was characterized by H-1 and C-13 NMR, 2D NMR, IR spectroscopy, and high-resolution mass spectrometry.
Article
Chemistry, Organic
Kris Antolinc, Helena Brodnik, Uros Groselj, Bogdan Stefane, Nejc Petek, Jurij Svete
Summary: Irradiation of mixtures of title diazonium salts and heteroarenes with green light (510 nm) in the presence of eosin Y disodium salt (EY-Na-2) as a photocatalyst furnishes the corresponding arylation products in 8-63% yields. This method has a broad substrate scope and serves as a metal-free alternative for the synthesis of 3-heteroaryl-substituted 4Hquinolizin-4-ones and azino-and azolo-fused pyrimidones with a bridgehead nitrogen atom.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Luka Ciber, Helena Brodnik, Franc Pozgan, Jurij Svete, Bogdan Stefane, Uros Groselj
Summary: In this study, a monosubstituted benzene-1,2-diamine building block was prepared in two steps from commercially available compounds, and two new compounds were successfully synthesized.
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.
