Article
Chemistry, Organic
Marina Tsuzaki, Shin Ando, Tadao Ishizuka
Summary: In this study, a method for etherification via aromatic substitution between two EWGs was developed. Under specific conditions, the conversion of challenging aromatic substrates to ether products was achieved successfully.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Dongxin Zhang, Lvjia Chen, Huiqing Deng, Ying Zhang, Qihang Cheng, Qian-Feng Zhang
Summary: Asymmetric ring-opening reactions of donor-acceptor cyclopropanes with 1,3-cyclodiones have been achieved for the synthesis of enantioenriched gamma-hydroxybutyric acid derivatives in the presence of Cu(ii)/trisoxazoline catalyst. These reactions provided the desired products in yields of 70% to 93% with enantiomeric excesses of 79% to 99%.
Article
Chemistry, Organic
Chengyu Yu, Guoren Yue, Penji Yan, Hai Song, Hucheng Shi, Yangfei Wei, Zhengen Song, Xin Jia
Summary: A novel synthesis of highly functionalized dihydrofuranyl alcohols has been developed through a tandem process, resulting in good yields of up to 97.1%.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Toreshettahally R. Swaroop, Kanchugarakoppal S. Rangappa, Lokman Torun
Summary: Carbimidothioates are synthesized by reacting Grignard reagents or heteroaryl lithium compounds with arylisothiocyanates followed by treatment with methyl iodide. These intermediates are then used to synthesize beta-enaminones by condensation with methyl ketones in the presence of sodium hydride in DMF, providing a new gateway for the synthesis of important building blocks in synthetic organic chemistry.
Article
Chemistry, Organic
Hongchen Li, Lidong Shan, Lin Min, Yunxiang Weng, Xinyan Wang, Yuefei Hu
Summary: A novel tandem synthesis of 1,3-disubstituted naphthalenes is developed using TfOH-promoted directed-aldol and Friedel-Crafts reactions. The discovery of a chemoselective directed-aldol reaction between different ketones with alpha-hydrogens enables the efficient creation of new C-C bonds and a benzene ring in one pot.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Francisco V. Gaspar, Marcelo F. M. F. Azevedo, Leonardo S. A. Carneiro, Samuel B. Ribeiro, Pierre M. Esteves, Camilla D. Buarque
Summary: This study reports the synthesis of new 4-acyl-1,2,3-triazoles through metal-free and solvent-free cycloaddition reactions, achieving high yields. The reaction mechanism for the synthesis of 4-acyl-1,2,3-triazoles was proposed based on experimental and theoretical data.
Article
Chemistry, Organic
Qi Xia, Xiang Li, Xi Fu, Yaxuan Zhou, Yanqing Peng, Jiayi Wang, Gonghua Song
Summary: A novel three-component reaction catalyzed by CuO in water has been developed, allowing the synthesis of a wide range of products containing 1,3/1,4-diketones. This method offers advantages such as the use of readily available starting materials, wide substrate scopes, excellent yields, gram-scale synthesis, and mild reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Sarwat Asma Ziya Ahmad, Faiz Ahmed Khan
Summary: A mild and transition-metal-free one-pot strategy was developed to synthesize polysubstituted naphthalene and phenanthrene derivatives from methyl enol ethers and alkynes. The reaction was promoted by boron trifluoride diethyl etherate at room temperature, leading to the formation of diverse functionalized compounds in good yields. The solvatochromism study of selected compounds revealed a positive solvatochromism effect in nitro-substituted naphthalene derivative.
Article
Chemistry, Organic
Ga Young Kook, Daegeun Kim, Min Ki Chae, Haye Min Ko
Summary: The transformation of N-sulfonyl-1,2,3-triazoles via insertion/rearrangement has been achieved using specific catalysts and suitable reaction conditions. The reaction proceeds under mild conditions, exhibits regio- and stereoselectivity, and has a broad substrate scope. Notably, the prevention of rearrangement allows access to (Z)-olefins, providing a new synthetic methodology.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Fatiha Nouali, Joana L. C. Sousa, Helio M. T. Albuquerque, Ricardo F. Mendes, Filipe A. Almeida Paz, Liza Saher, Zahira Kibou, Nouredine Choukchou-Braham, Oualid Talhi, Artur M. S. Silva
Summary: The synthesis of 4,6-disubstituted isoindoline-1,3-diones through microwave-assisted Diels-Alder reactions is reported. A range of chromones and maleimides were utilized to investigate the reaction scope. The proposed mechanism involves a Diels-Alder reaction, ring opening, and in situ oxidation. The yields of 4,6-disubstituted isoindoline-1,3-diones ranged from 15% to 59%, with N-phenylmaleimide showing the highest reactivity in producing the desired product.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Biochemistry & Molecular Biology
Mohammad Abbasi, Najmeh Nowrouzi, Sara Sajedinia
Summary: We present a one-pot, efficient oxidative-condensation process using DMSO/I-2 to construct 4-alkyl and 4-aryl-5-(arylthio) thiazol-2-amines. Various alkyl and aryl methyl ketones can be successfully synthesized under these reaction conditions.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Multidisciplinary
Xu Zhang, Di Wang, Mengfan Chang, Xuefeng Xu, Wenguang Li, Wanya Wang
Summary: A practical and efficient palladium-catalyzed selective dehydrogenative [4+2] annulation of 2-methyl-1,3-cycloalkanediones with olefins was developed, leading to the synthesis of polysubstituted dihydropyran derivatives.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Organic
Qingqing You, Mingjie Liao, Huangdi Feng, Junhai Huang
Summary: The decarboxylation or decarboxylative coupling reactions of carboxylic acids and their derivatives are essential tools for organic synthesis. Microwave-assisted technology, recognized by both industry and academia, has been employed for sustainable organic synthesis. This review focuses on the recent developments in microwave-assisted decarboxylative reactions, including transition-metal-catalyzed and metal-free approaches.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Yujiro Hayashi, Masashi Tomikawa, Naoki Mori
Summary: A three-pot asymmetric synthesis method was developed to produce anti-1,3-diol unit through three sequential reactions, including enantioselective Aldol reaction, diastereoselective anti-epoxidation, and reductive opening of the epoxide, achieving excellent diastereo- and enantioselectivity.
Article
Chemistry, Applied
Yi-En Liang, Balaji D. Barve, Yao-Haur Kuo, Hsu-Wei Fang, Ting-Shen Kuo, Wen-Tai Li
Summary: A base-mediated, green, microwave-assisted efficient method for the synthesis of a diverse benzoxanthone library from readily accessible gamma-alkynyl 1,3-diketones was reported in this study. The synthesis involves tandem reactions including intramolecular cyclization, propargyl-allenyl isomerization, and electrocyclization in one pot, resulting in the formation of new C-C and C-O bonds.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
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.