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Supramolecular Catalysts for Organic Synthesis: Preparation and Applications of Cyclodextrins and Calixarenes in C-C Cross-Coupling Reactions Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-17 Carolina G. S. Lima, Fernanda P. Pauli, Vinicius G. Madriaga, Adriane A. P. Amaral, Isabela A. Graciano, Vinicius L. Meira, Luana da S. M. Forezi, Vitor F. Ferreira, Thiago de M. Lima, Fernando de Carvalho da Silva
Reactions that promote the formation of carbon-carbon bonds are of great importance in organic synthesis, since those transform available, relatively inexpensive, and small organic molecules into the more complex ones. One of the main protocols used for these transformations are cross-coupling reactions, and due to their versatility and applications, several efforts have been devoted recently into
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Copper-Catalyzed Multicomponent Reaction to Construct Fluorinated Indole-quinoxalin-2(1H)-ones and Their Biological Evaluation Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-15 Letian Zhang, Yong Yang, Pengfei Zhang, Chao Chen, Chao Shen
A practical and mild three-component reaction between indoles, quinoxalin-2(1H)-ones, and CF3SO2Na is disclosed for the facile access of various 3-[2-(trifluoromethyl)1H-indol-3-yl]quinoxalin-2(1H)-ones using low-cost and catalytic amount of CuF2 as the catalyst. This strategy includes merits of high site-selectivity, step economy, and broad substrates scope. Synthetic utility was demonstrated by the
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Lewis Acid-Catalyzed (3+2) Cycloaddition of 2-Indolylmethanols with β,γ-Unsaturated α-Ketoesters Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-15 Shuang Yang, Hai-Qing Wang, Jun-Nan Gao, Wen-Xin Tan, Yu-Chen Zhang, Feng Shi
A Lewis acid-catalyzed (3+2) cycloaddition of 2-indolylmethanols with β,γ-unsaturated α-ketoesters was established, which afforded a series of cyclopenta[b]indoles in overall high yields (up to 98%) with excellent diastereoselectivities (up to >95:5 dr). This reaction not only represents the first C3-nucleophilic (3+2) cycloaddition of 2-indolylmethanols, but also provides a good example for (2+n)
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Anion Responsive Molecular Switch Based on a Doubly-Strapped Calix[4]pyrrole Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-15 Kaisa Helttunen
A calix[4]pyrrole receptor bearing two proximally meso - meso linking isophthaloyl straps displays open and closed states depending on the calix[4]pyrrole conformation. In the crystal structures and in non-polar solvent, the calix[4]pyrrole adopts open 1,3-alternate conformation with straps on the sides. Anion binding triggers a closed state of the receptor providing two types of interactions with
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Cobalt Porphyrin-Catalysed Synthesis of Azobenzenes by Dehydrogenative Coupling of Anilines Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-15 Caterina Damiano, Matteo Cavalleri, Nicola Panza, Emma Gallo
The demand for azobenzenes has exponentially grown due to their wide range of applications in textile, medical, and dye industries. Here we report a procedure to synthesise azobenzenes by the dehydrogenative coupling of anilines in the presence of CoII(TPP) (TPP = dianion of tetraphenyl porphyrin) catalyst and 4‑nitrophenyl azide oxidant species. Differently substituted azobenzenes were obtained in
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Syntheses of 7-, 8- and 9-Bromobenzotropolone, Cross-Couplings of Their Methyl Ethers, and Deprotection to 7-, 8- or 9-Substituted Benzotropolones Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-15 Reinhard Brückner, Philip Koblischek
Unprotected 6,7-benzotropolone and bromine were known to undergo an electrophilic substitution delivering the 7-bromo derivative; it was carried on as its methyl ether. O-Acety l-6,7-benzotropolone added bromine at the C 8 =C 9 bond whereupon an amine-induced E1 cb elimination led to the 8-brominated benzotropolone acetate; ester cleavage with aqueous acetic acid and etherification with diazomethane
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Mechanistic Insights of Lewis Acid-Controlled Torquoselective Nazarov Cyclization of Activated Dienones Bearing a Chiral Sulfoxide Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-14 Erwann Grenet, Raphaël Robidas, Arie van der Lee, Claude Y. Legault, Xavier J. Salom-Roig
This work provides a switchable strategy to access, via a Nazarov cyclization, two diastereomeric disubstituted 3,4,5,6-tetrahydrocyclopenta[ b ]pyran-7(2H)-ones from an activated dienone bearing a chiral sulfoxide. The switch in the torquoselectivity is controlled by the nature of the Lewis acid used as promoter. From the four possible stereoisomers, only the two trans were observed. The Lewis acids
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Selective Electrochemical Dibromination of Terpenes and Naturally Derived Olefins Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-12 Lilla G. Gombos, Leo Werner, Dieter Schollmeyer, Carlos A. Martínez-Huitle, Siegfried R Waldvogel
A simple electrochemical protocol is established for the selective alkene dibromination of naturally derived olefins, such as terpenes. The use of hazardous Br 2 or its analogues have been elegantly avoided by employing readily available, inexpensive and harmless sodium bromide with a dual role as reagent and supporting electrolyte in combination with sustainable carbon-based electrodes. This electrochemical
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Visible-Light-Induced Acylation/Arylation of Alkenes via Aryl Migration/Desulfonylation Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-11 Zhen-Tao Luo, Jian-Hong Fan, Bi-Quan Xiong, Yu Liu, Peng-Fei Huang
A photoinduced acylation/arylation of N -(arylsulfonyl)acrylamide with acyl oxime esters through a nitrogen-centered radical protocol has been disclosed for the preparation of functionalized indolin-2-ones, which proceeds through a cascade acyl radical addition of carbon-carbon double bond, aryl migration, desulfonylation, and intramolecular cyclization sequence. This redox-neutral strategy features
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Synthesis of Oxazole–Tetrahydropyran Hybrids and Study on Their Antiproliferative Activity Against Human Tumour Cells Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-11 Vanesa Quintana, Aday González-Bakker, Juan I. Padrón, Víctor S. Martín, José M. Padrón, Danilo Davyt, Guillermo Valdomir
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Six-Component Reactions and Beyond: The Nuts and Bolts Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-11 Seyyed Emad Hooshmand, Hossein Yazdani, Christopher Hulme
The deployment of multicomponent reactions (MCRs), defined as containing three or more reactants, not only enjoys pot, atom, and step-economy in the synthesis of novel complex molecules but also aligns with sustainable chemistry principles as a green symphony. Generally, more components lead to more complexity, and are taken to an extreme ‘‘higher-order’’ MCRs, where six or even more components react
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Dual Palladium-Photoredox catalyzed C-H functionalization Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-09 Partha Sarathi Saha, Purushothaman Gopinath
Functionalization of an unactivated C-H bonds is a highly desirable process in organic chemistry as it gives direct access to many new functional groups in a single step. This process is generally achieved using transition metal catalysts and among the transition metals studied for C-H activation, palladium plays an important role due to its unique reactivity. Photoredox catalysis has witnessed a huge
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Photochemical 1,3-Acyl Shifts in Natural Product Synthesis Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-09 Dennis Lübken, Björn Siekmeyer, Markus Kalesse
Photochemical, sigmatropic 1,3-acyl shifts represent a powerful tool to construct quaternary carbon atoms and the backbones of complex natural products which cannot be constructed easily by conventional methods. This review highlights applications of 1,3-acyl shifts to elegant, partly biomimetic total syntheses of natural products by discussing the underlying photochemical equilibrium.
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Cyclobutane Formation by the Reaction of Ethenesulfonyl Fluoride with Dimethyl Diazomalonate Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-09 Le Li, Peter Mayer, Armin R. Ofial, Herbert Mayr
Attempts to synthesize fluorosulfonyl-substituted pyrazolines by Huisgen reactions (1,3-dipolar cycloadditions) of dimethyl diazomalonate with ethenesulfonyl fluoride led to the formation of dimethyl (2R*,3S*,4R*)-2-(1,3-dimethoxy-1,3-dioxopropan-2-yl)-3-(fluorosulfonyl)-4-((fluorosulfonyl)methyl)cyclobutane-1,1-dicarboxylate, a highly substituted cyclobutane derivative, which was characterized by
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Synthesis of Glycal Amides from Amino Acid Esters by Carbonylative Coupling Reaction Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-08 Jessica C. De Jesus, Henrique K. Noguchi, Mônica F. Z. J. Toledo, Robert A. Burrow, Daniel C. Pimenta, Hélio A. Stefani
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Amine-Rich Carbon Dots as Novel Nano-Aminocatalytic Platforms in Organic Synthesis Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-08 Vasco Corti, Beatrice Bartolomei, Martina Mamone, Giuseppe Gentile, Maurizio Prato, Giacomo Filippini
The development of novel and effective metal-free catalytic systems, which can drive value-added organic transformations in environmentally benign solvents (for instance, water), is highly desirable. Moreover, these new catalysts need to be harmless, easy-to-prepare, and potentially recyclable. In this context, amine-rich carbon dots (CDs) have recently emerged as promising nano-catalytic platforms
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Cyclic Triimidazoles as Stabilizers for Gene Promoter and Human Telomeric DNA G-Quadruplexes Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-08 Daniele Malpicci, Stefano Andolina, Stefano Di Ciolo, Elena Lucenti, Elena Cariati, Simona Marzano, Bruno Pagano, Jussara Amato, Antonio Randazzo, Clelia Giannini
The synthesis and characterization of a small series of cyclic triimidazole derivatives functionalized with methylated pyridines or guanidines moieties is reported. These compounds were tested for their ability to bind to G-quadruplexes from both telomeric and oncogene promoter sequences. Some of them exhibited high affinity and effective G-quadruplex-stabilizing properties. Overall, these compounds
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Computational Comparison of the Stability of Iminium Ions and Salts from Enals and Pyrrolidine Derivatives (Aminocatalysts) Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-08 Anna M. Costa, Alejandro Castro-Alvarez, Jaume Vilarrasa, Daniel Fillot
The energies of CH2=CH–CH=NR2 + + HNR*2 = CH2=CH–CH=NR*2 + + HNR2 reactions (exchange of propenal between two secondary amines) and of similar equilibria with cinnamaldehyde have been calculated and compared. Iminium ions from pyrrolidines with substituents that can help stabilize the positive charge are especially stable in the gas phase, as expected, whereas in very polar solvents the predicted order
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1,3-Dipolar Cycloaddition of Alkanone Enolates with Azides in Deep Eutectic Solvents for the Metal-free Regioselective Synthesis of Densely Functionalized 1,2,3-Triazoles Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-08 Luciana Cicco, Filippo Maria Perna, Aurelia Falcicchio, Angela Altomare, Francesco Messa, Antonio Salomone, Vito Capriati, Paola Vitale
An eco-friendly metal-free protocol was developed for the regioselective synthesis of densely functionalized 1,2,3-triazoles via a 1,3-dipolar cycloaddition reaction of alkanone enolates with azides performed in the environmentally responsible choline chloride/urea or choline acetate/urea eutectic mixture. This approach displays a broad substrate scope, straightforwardly furnishing the desired triazoles
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Selective Cyclopropanation/Aziridination of Olefins Catalyzed by Bis(pyrazolyl)borate Cu(I) Complexes Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-08 Qianyi Zhao, Qiu-Yue Yao, Yan-Jiao Zhang, Ting Xu, Jie Zhang, Xuenian Chen
Bis(pyrazolyl)borate complexes [BBN(pz R ) 2 ]Cu(I) were evaluated as catalysts in the reaction of carbene/nitrene transfer and addition to C=C bonds of a wide range of aromatic, heterocyclic and aliphatic olefins. The complexes exhibit high catalytic efficiency and selectivity in both processes.
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Stereoconvergent Synthesis of Cyclopentenyl Nucleosides by Palladium-Assisted Allylic Reaction Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-07 Anna Esposito, Giovanni Talarico, Maria De Fenza, Daniele D'Alonzo, Annalisa Guaragna
The Tsuji-Trost reaction of cyclopentenyl carbonates was explored by experimental studies and computational calculations, in search for the synthetic conditions enabing the stereoconvergent synthesis of cyclopentenyl nucleosides. Under common conditions, cyclopentenyl reagents provide Tsuji-Trost products only in a weakly stereoconvergent manner. However, changes in the amount of catalyst (up to 1
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Access to Ketones through Palladium-Catalyzed Cross-Coupling of Phenol Derivatives with Nitroalkanes Followed by Nef Reaction Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-06 Xiaoyu He, Sengui Hu, Yuxuan Xiao, Lin Yu, Wengui Duan
A practical protocol for the synthesis of ketones by Pd-catalyzed cross-coupling of phenol derivatives with nitroalkanes followed by a Nef-type reaction has been developed. The readily available nitroalkanes served as alkyl nucleophiles under basic conditions to couple with easy-to-handle phenol derivatives derived from naturally abundant phenols. The avoidance of using organometallics and organic
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6-Methylquinazolin-4(3H)-one Based Compounds as BRD9 Epigenetic Reader Binders: A Rational Combination of in silico Studies and Chemical Synthesis Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-05 Ester Colarusso, Erica Gazzillo, Eleonora Boccia, Assunta Giordano, Maria Giovanna Chini, Giuseppe Bifulco, Gianluigi Lauro
6-methylquinazolin-4(3H)-one-based compounds were here identified and synthesized as novel binders of bromodomain-containing protein 9 (BRD9) epigenetic reader. Accounting a fast and efficient synthetic route aimed to easily obtain differently 2- and 8-disubstituted 6-methylquinazolin-4(3H)-one derivatives, a virtual library of synthesizable items was built and submitted to molecular docking experiments
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Cupric Halide-Promoted Stereoselective Intramolecular cis-Addition to Construct (Z)-Chloro(Bromo)benzo[c,d]indoles Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-05 Hanying Diao, Li Liu, Jin Wang, Yanfei Lin, Xiangyuan Zhao, Heyang Zeng, Senlei Shi, Wei Gao, Long Yang, Guanben Du, Lianpeng Zhang
A convenient and efficient method for one pot synthesis of polysubstituted (Z)-halobenzo[c,d]indoles from 8-alkynyl-1-naphthylamine derivatives using CuCl2 and CuBr2 as the halogenated reagents has been developed. In this protocol, both (Z)-chloro and bromobenzo[c,d] indole derivatives can be obtained in moderate to good yields by copper halide-promoted stereoselective intramolecular cis-addition annulation
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Efficient Construction of Tetracyclic 1,2,4-triazoline-Fused Dibenzo[b,f][1,4]oxazepines through KI/TBHP-Mediated [3+2] Annulation between DBO-Imines and N-Tosylhydrazones Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-05 Chuan-Chuan Wang, Xin-Lu Wang, Degang Ding, Zhi-Wei Ma, Zhijing Liu, Xiao-Pei Chen, Ya-Jing Chen
The KI/TBHP (tert-butyl hydroperoxide) promoted [3+2] annulation between dibenzo[b,f][1,4]oxazepine-imines (DBO-Imines) and N-tosylhydrazones under mild conditions has been developed, affording a direct and high atom-economical preparation for tetracyclic 1,2,4-triazoline-fused dibenzo[b,f][1,4]oxazepines (DBOs) in good to excellent yields. This procedure could tolerate a wide range of functional groups
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Sequential Base-Promoted Formal [4+2] Allenoate Based Cycloaddition: An Efficient Strategy for the Synthesis of Functionalized Acridines Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-05 Toktam S. Shirazian, Hossein Zahedian Tejeneki, Ali Nikbakht, Frank Rominger, Saeed Balalaie
Base-promoted formal [4+2] cycloaddition reaction of ( Z )-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes and allenoates represents an efficient method for the synthesis of functionalized acridines via a sequential Michael addition, aldol condensation, and isomerization process in a mild condition. This new approach tolerates a wide range of ( Z )-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes
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4,4-Difluorospiro[2.2]pentan-1-yl – A Fluorinated Substituent to Expand the Synthetic and Medicinal Chemists’ Toolbox Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-04 Kostiantyn P. Melnykov, Olena V. Voloshyna, Bohdan V. Vashchenko, Oleksandr P. Demchuk, Oleksandr V. Hryshchuk, Oleksandr O Grygorenko
Functionalized 4,4-difluorospiro[2.2]pentan-1-yl derivatives are proposed as promising building blocks for synthetic and medicinal chemistry. Scalable, efficient, and diastereoselective approach to their preparation via the difluorocyclopropanation of (2-methylenecyclopropyl)methanol is developed. Stability of the title scaffolds towards common reaction conditions is confirmed by a series of typical
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A Solid Alkylation: Highly Recyclable, Flow Chemistry-Ready, Resin-Supported Thioimidazoliums Alkylate Sulfur-Centered Nucleophile Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-04 Vincenzo Alessandro Cataldo, S. Maryamdokht Taimoory, Sanam Mohammadzadeh, Ryan Guterman, John Trant
A series of readily regenerable thioimidazolium-based ionic liquids possessing the ability to transfer an alkyl group to a nucleophile are immobilized on crosslinked polystyrene beads. Different alkyl groups can be loaded onto the resin, highlighting the tunability of the material. The efficiency of these materials is demonstrated by their screening against a series of nucleophiles, showing a particular
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Complementary Cooperative Catalytic Systems in the Aerobic Oxidation of a Wide Range of Si–H-Reagents to Si–OH-Products: From Monomers to Oligomers and Polymers Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-03 Irina K. Goncharova, Rinat S. Tukhvatshin, Roman A. Novikov, Alexander D. Volodin, Alexander A. Korlyukov, Valentin G. Lakhtin, Ashot Arzumanyan
The article presents an in-depth study of the applicability of cooperative [M]-/Organo-catalytic systems in aerobic Si–H-functionalization. A thorough kinetic study allowed us to identify two “complementary” catalytic systems based on earth-abundant [M]-catalysts and inexpensive commercially available organic catalysts. The first system, Co(OAc) 2 /N-hydroxysuccinimide, made it possible to oxidize
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20π Antiaromatic Isophlorins without Metallation or Core Modification Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-03 Haruna Sugimura, Kana Nakajima, Ken-ichi Yamashita, Takuji Ogawa
Isophlorins (two-electron-reduced porphyrins) with 20π antiaromaticity have been synthesized by metallation or core modification (replacing the inner NHs with less bulky atoms) thus far. The core-modification number (CMN) is an important factor for the stability of isophlorins against their oxidation to porphyrins. However, isophlorins with small CMN (≤ 2), i.e., without significant core modification
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Schiff bases and multidentate organic compounds as fluorescent sensors of Al3+: photophysical, fluorescent bioimaging and the mechanisms Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-03 Jessica C. Berrones-Reyes, Blanca M. Muñoz-Flores, Manuel A. Treto-Suárez, Yoan Hidalgo-Rosa, Eduardo Schott, Dayán Páez-Hernández, P. M. Gurubasabaraj, Ximena Zarate, Víctor M. Jiménez Pérez
Aluminium is the most abundant metal in the earth crust and so far, there is no evidence on an important role on the human body and it is well known the relation aluminium exposure on human health and aluminium-related diseases. The aim of this review is to attempt to know the most recent advances on multidentate organic compounds such as naphthalene, coumarin, quinoline, Schiff bases, benzothiazole
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Iron-Based Imidazolium Salt as Dual Lewis Acid and Redox Catalyst for the Aerobic Synthesis of Quinazolines Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-02 Mario Martos, Isidro Manuel Pastor
A low transition temperature mixture formed with 1-butyl-3-(methoxycarbonylmethyl)imidazolium chloride and iron(III) chloride has proven to be an efficient catalyst for the synthesis of quinazolines following a sequence of condensation-cyclization-oxidation reactions. The protocol is simple and effective for coupling 2-acylanilines and benzylamines to form nitrogen containing heterocycles with moderate
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Catechol-Functionalized Carbon Nanotubes as Support for Pd Nanoparticles: a Recyclable System for the Heck Reaction Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-02 Alessandro Mercadante, Vincenzo Campisciano, Anthony Morena, Laura Valentino, Valeria La Parola, Carmela Aprile, Michelangelo Gruttadauria, Francesco Giacalone
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Recent developments in the synthesis of polyhydroxylated indolizidines Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-02 Paula Fraňová, Štefan Marchalín
Since their discovery, polyhydroxylated indolizidines have been the focus of attention for both biologists and synthetic chemists. They are classified as iminosugar alkaloids: nitrogen-based carbohydrate mimetics that are potent inhibitors of glycosidases. Many discovered glycosidase inhibitors were found to possess biological activity, and they are therefore considered to be potential therapeutics
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Base-mediated C4-selective C-H-sulfonylation of pyridine. Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-02 Marius Friedrich, Georg Manolikakes
The direct regioselective C-H-functionalization of simple, unfunctionalized pyridines is considered a long-standing challenge in heterocyclic chemistry. Herein, we report a novel one-pot protocol for the C4-selective sulfonylation of pyridines via triflic anhydride (Tf2O) activation, base-mediated addition of a sulfinic acid salt and subsequent elimination/rearomatization. Contrary to previous approaches
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Multicomponent Functionalization of the Octreotide Peptide Macrocyclic Scaffold Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-01 Aldrin V. Vasco, Leonardo G. Ceballos, Ludger A. Wessjohann, Daniel García Rivera
The replacement of the disulfide bridge by other types of side chain linkages has been a continuous endeavor in the development of cyclic peptide drugs with improved metabolic stability. Octreotide is a potent and selective somatostatin analog that has been used as an anticancer agent, in radiolabeled conjugates for the localization of tumors and as targeting moiety in peptide-drug conjugates. Here
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Synthesis of open-cage fullerenes containing a H-bond between the encapsulated water molecule and the amide moiety on the rim of the orifice Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-08-01 Zhen Liu, Rui Gao, Zeyu Liu, Hong Fei Han, Jie Su, Peng Jin, Liangbing Gan
Further hydrolysis of an open-cage fullerene derivative with an epoxy moiety on the rim of the orifice led to the formation of a new open-cage fullerene with a 17-membered orifice and an amide group directly above the orifice. The water encapsulation ratio in the new open-cage compound reached 100% as a result of heating with water at 80 O C. The amide group above the orifice completely blocks the
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Asymmetric Cycloaddition/Annulation Reactions by Chiral Phosphoric Acid Catalysis: Recent Advances Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-31 Alemayehu Gashaw Woldegiorgis, Suleman Muhammad, Xufeng Lin
Asymmetric cycloaddition/annulation reactions have contributed greatly to the synthesis of a variety of novel cyclic compounds used in organic synthesis, natural product synthesis, material science, and chemical biology. Thus, chiral phosphoric acid-catalyzed asymmetric cycloaddition reactions have received the attention of synthetic community to design new vital asymmetric reactions and synthesize
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Rh(III)-Catalyzed N-Arylation of Alkyl Dioxazolones with Arylboronic Acids for the Synthesis of N-Aryl Amides Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-28 Jia-Lin Song, Shao-Yong Chen, Lin Xiao, Xiao-Ling Xie, Yi-Chuan Zheng, Zhang Shang-Shi, Bing Shu
Herein, an method for N -aryl amides preparation has been established via Rh(III)-catalyzed C(sp 2 )- N cross-coupling reactions of alkyl dioxazolones with arylboronic acids, heterocyclic boronic acid, and alkenyl boronic acid. This efficient and straightforward catalytic approach was featured with broad substrate scope (38 examples), good functional group compatibility, high yields (up to 99%) and
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Synthesis of Benzothiazinones from Benzoyl Thiocarbamates: Application to Clinical Candidates for Tuberculosis Treatment Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-28 William Connors, Ryan DeKorte, Simon C. C. Lucas, Ariamala Gopalsamy, Robert E Ziegler
Benzothiazinones are a structural motif found in biologically active compounds, such as the clinical candidates BTZ-043 and Macozinone for the treatment of tuberculosis. We describe a robust, two-step method to synthesize 2-amino-substituted benzothiazinones from benzoyl thiocarbamates, which were prepared in a one-pot procedure from benzoyl chlorides. The intramolecular cyclization and ethoxy displacement
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C–H Activation Based Functionalizations of Furfural Derivatives Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-28 Alessia Mori, Sebastien Curpanen, Cristofer Pezzetta, Alejandro Perez-Luna, Giovanni Poli, Julie Oble
Furfural and related compounds are building blocks of industrial interest, obtained from renewable raw biomasses containing C5- and C6-monosaccharides. In recent years, their use as precursors of basic and fine chemicals has gained increasing attention as a green alternative to petroleum-derived compounds. Several works have reported the functionalization of furfurals to obtain a wider range of chemicals
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Hypervalent Iodine-Mediated Azidation Reactions Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-28 Irina A. Mironova, Stefan F. Kirsch, Viktor Zhdankin, Akira Yoshimura, Mekhman S. Yusubov
Organic azides have found wide application in various fields of science and technology. This review summarizes recently developed approaches to the direct, one-step synthesis of diverse organic azides utilizing hypervalent iodine reagents. The first part of review deals with the azidation using unstable azidoiodinanes generated in situ from common hypervalent iodine reagents (such as diacetoxyiodobenzene
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Trifluoromethylated Indolopyranones through Regioselective Annulation of Indole Carboxylic Acids with Unsymmetric Internal Trifluoromethylated Alkynes Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-27 Xingxing Zhang, Guangyuan Liu, Yiyuan Peng, Hua li, Yirong Zhou
A rhodium-catalyzed oxidative cross coupling/annulation of indole carboxylic acids with unsymmetric internal trifluoromethylated alkynes was accomplished for direct access to diverse trifluoromethylated indolopyranones, which combined indole, pyranone and trifluoromethyl, three valid pharmacophores, into one molecule. Both indole-3-carboxylic acids and indole-2-carboxylic acids proved to be suitable
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Cu-Catalyzed Asymmetric Allylic Alkylation of Racemic Cyclic Allyl Bromides with Organolithium Compounds Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-27 Jun Li, Xiao Song, Fusong Wu, Hengzhi You, Fen-Er Chen
Organolithium reagents are one of the most widely used reagents in chemical synthesis. Herein, we reported the first study of organolithium reagents used in asymmetric allylic alkylation (AAA) reactions with racemic cyclic substrates. A simple and efficient Cu-catalyzed synthesis of enantiomerically enriched cycloalkene derivatives from various racemic cyclic allylic bromides was developed. The standard
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Organocatalytic synthesis and anti-trypanosomal activity evaluation of L-pentofuranose-mimetic iminosugars Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-27 Juan Manuel Mesa, Marcelo Alberto Comini, Estefania Dibello, Daniela Gamenara
A series of L-lyxo and L-xylo- pentofuranose-mimetic iminosugars and derivatives were efficiently synthesized in a stereoselective manner, through a concise strategy which involves an organocatalyzed Mannich reaction of an imine and a protected dioxanone as key step, using D-proline as catalyst. A prelimiary evaluation of their activity as potential anti-trypanosomal agents was studied. One of the
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Direct Functionalization of Lithium Phosphine Oxides bearing an Alkyne chain Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-26 Hamdi Sanaa, Ali Samarat, Muriel Durandetti
An efficient synthesis of functionalized alkynyl phosphine oxides is described. The current approach is based on the activation of the phosphorus–hydrogen bond (P–H bond) of a secondary phosphine oxide. After the deprotonation step using n -butyllithium, the in-situ generated LiP(O)RR’ undergoes further condensation with a wide variety of electrophiles, and without a cyclisation step into the alkyne
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Copper-Catalyzed Synthesis of O/N-alkyl S-phenyl Phenylcarbamothioates: An Odorless and Chemo-selective Chan-Lam Reaction to Construct C-S Bond Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-26 Yu-Xi Wu, Xi Wang, Jing-Hang Li, Hua-Qing Xiao, Zhi-Bing Dong
A simple and efficient synthetic method to structure C–S bonds was established based on Chan-Lam reaction. A series of O/N -alkyl S -phenyl phenylcarbamothioates were obtained in good yields by using odorless O/N -alkyl phenylthiocarbamates as sulfur sources and commercially available phenylboronic acids as substrates catalyzed by Cu(OAc) 2 . This methodology features simple performance, odorless sulfur
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Ring rearrangement of 1,3-azasilinyl-4-epoxides to synthesize 2silamorpolines by a Si-C bond migration/oxidation process Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-25 Song Zhou, Xiaoyu Tu, Yuanhang He, Lu Gao, Zhen Lei Song
PhI(OAc) 2 /CuI-promoted ring rearrangement of 1,3-azasilinyl-4-epoxides has been developed. The reaction proceeds by a Si-C bond migration/oxidation process, leading to structurally novel 2-silamorpolines containing an aryl/aldehyde groups-substituted quaternary carbon.
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Stereospecific Access to α- and β-N-Glycosylamine Derivatives by a Metal Free O-to-N [3,3]-Sigmatropic Rearrangement Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-27 Debora Pratesi, Stefania Mirabella, Giulia Petrucci, Camilla Matassini, Cristina Faggi, Francesca Cardona, Andrea Goti
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Asymmetric Synthesis of Halocyclized Products by Using Various Catalysts: A State-of-the-Art Review Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-25 Soumik De, Aritra Kumar Dan, Raghaba Sahu, Debadutta Das
Halogens play a crucial part in synthetic organic chemistry. The excellent electrophilicity properties and the leaving group abilities are responsible for the activation and structural derivation of various organic compounds. The cyclization reactions in the presence of halogens allow the researchers to construct diverse carbocycles and heterocycles. The halogen-induced cyclization reactions work very
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Separation of the Thorpe−Ingold and Reactive Rotamer Effect by Using the Formation of Bicyclic Aziridinium Ions Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-26 Tim Helbing, Michael Kirchner, Jonathan Becker, Richard Göttlich
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Near-Infrared and Dual Emissions of Diphenylamino Group-Substituted Malachite Green Derivatives Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-26 Toshiaki Mori, Kohei Sekine, Kyohei Kawashima, Toshifumi Mori, Yoichiro Kuninobu
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Advances in the Synthesis of Biscarboranes Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-25 Ke Cao, Cai-Yan Zhang
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Calix[n]arenes in Action: Recent Applications in Organocatalysis Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-25 Juliana Baptista Simões, Daniel Leite da Silva, Sergio Antonio Fernandes, Ângelo de Fátima
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Tris(pyridin-2-ylmethyl)amine-Based Ion Pair Receptors for Selective Lithium Salt Recognition Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-24 Ju Ho Yang, Jaehyeon Kim, Benjamin P. Hay, Kyounghoon Lee, Sung Kuk Kim
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Cross-Coupling of C−H and N−H Bonds: A Hydrogen Evolution Strategy for the Construction of C−N Bonds Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-22 Lekkala Ravindar, Siti Aishah Hasbullah, Nurul Izzaty Hassan, Hua-Li Qin
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DNA-Templated Formation and N,O-Transacetalization of N-Methoxyoxazolidines Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-22 Aapo Aho, Tommi Österlund, Jani Rahkila, Pasi Virta
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α-Angelica Lactone Catalyzed Oxidation of Pyrrolidines to Lactams Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-22 Siddharth K. Deepake, Manish Kumar, Pawan Kumar, Utpal Das
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Polymer-Bound Halogen Bonding Organocatalysis** Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-22 Raffaella Papagna, Dana Kutzinski, Stefan M. Huber
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Cu(I)-Catalyzed Enantioselective γ-Boryl Substitution of Trifluoromethyl- and Silyl-Substituted Alkenes Eur. J. Org. Chem. (IF 3.261) Pub Date : 2022-07-22 Natsuki Oyama, Sota Akiyama, Koji Kubota, Tsuneo Imamoto, Hajime Ito