Synthesis of 1,2,3-fused indole polyheterocycles via copper catalyzed cascade reaction Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-18 Ching-Fa Yao
A one-pot synthesis of 1,2,3-fused indole polyheterocycle starting from 2-iodobenzamide and 2-iodobenzyl cyanide in the presence of coppoer catalyst is described. The cascade process that involves one C-C and thre C-N bond formation efficiently has a broad substrate scope.
DBU-Catalyzed Carbonylative Cyclization of Propargylic Alcohols with Elemental Sulfur Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-18 Xiao-Feng Wu, Yuya Hu, Zhiping Yin, Thomas Werner, Anke Spannenberg
A novel carbonylation procedure on the cyclization of propargylic alcohols with elemental sulfur has been developed. With DBU as the catalyst, elemental sulfur and carbon monoxide can be activated and incorporated into the propargylic alcohols. Good to excellent yields of the desired sulfur containing heterocyles can be produced at room temperature.
Rational Design of a Metallo-catalytic Cavitand for Regio-selective Hydration of Specific Alkynes Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-17 Tetsuo Iwasawa, Naoki Endo, Mami Inoue
A new synthesis and design of functionalized supramolecular cavitand with inwardly oriented Au(I) and P=O is described, including a description of its catalytic proclivity in selective hydration of internal alkynes. The cavitand works as a supramolecular flask device: the Au(I) coordinates to the triple bond, and the P=O connects with a H2O, and the cavity favored to fold a single alkynyl side-chain. Several tests of different substrate patterns indicated that the cavity has substrate specificity like as enzymatic catalysis.
Cu(I) mediated degradation of polysaccharides leads to fragments with narrow polydispersities Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-17 Jani Rahkila, Filip Ekholm, Reko Leino
Biomass derived oligo- and polysaccharides are important compounds for various applications, including biomedicine and material science. Their use, however, is often limited by inherent structural inhomogeneity of the starting materials. Here, a method for depolymerization of naturally occurring polysaccharides, including dextran, starch, xylan and galactoglucomannan, into well-defined fragments of narrow polydispersities is described, based on the use of in situ generated Cu(I) species under the commonly employed CuAAC reaction conditions. The main strength of the reported method is its high versatility, both in terms of substrate scope and operational simplicity.
Preparation and Optical and Electrochemical Properties of Phthalocyanines with Four or Eight Diphenylphosphino, Diphenylphosphineoxide, and Diphenylphosphinesulfide Groups Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-17 Takeshi Kimura, Hiroki Muraoka, Shiduko Nakajo, Satoshi Ogawa, Satoshi Yamamoto, Nakao Kobayashi
Several phthalocyanines (Pcs), where four or eight phosphines are directly linked to their periphery, have been prepared. The starting materials, 4-(diphenylphosphino)-5-chlorophthalonitrile (2), 4,5-bis(diphenylphosphino)phthalonitrile (3), and 4-(diphenylphosphino)-5-(diphenylphosphoryl)-phthalonitrile (4), were prepared by the reaction of 4,5-dichlorophthalonitrile (1) and diphenyltrimethylsilylphosphine in toluene at 110 °C. Compound 2 was treated with Li in hexan-1-ol at 120 °C, to produce tetrakis(diphenylphosphino)tetrachloroPc [Pc(PPh2)4Cl4, 11], while refluxing 3 in ethoxyethanol in the presence of DBU yielded octakis(diphenylphosphino)Pc [Pc(PPh2)8, 12]. The reactions of 11 with mCPBA or elemental sulfur produced tetrakis(diphenylphosphoryl)tetrachloroPc [Pc(POPh2)4Cl4, 13] or tetrakis(diphenylthiophosphinyl)tetrachloroPc [Pc(PSPh2)4Cl4, 15], respectively, while that of 12 with mCPBA or elemental sulfur afforded octakis(diphenylphosphoryl)Pc [Pc(POPh2)8, 14] or octakis(diphenylthiophosphinyl)Pc [Pc(PSPh2)8, 16], respectively. Octakis(diphenylphosphino)-octafluorophthalocyaninato magnesium [Pc(PPh2)8F8Mg, 17] was prepared from tetrafluorophthalonitrile (6) via 2 step reactions. The structures of simplified model compounds, 11a—16a, were optimized using the DFT method with the Gaussian 09 program. The optimized structures were utilized to calculate the HOMO and LUMO orbital energies, and the electronic transitions in the absorption spectra by the TD-DFT method.
2-Thiabicyclo[3.3.1]nonanes Construction via Organocatalytic Asymmetric Formal [3+3] Cycloaddition Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-16 Dhevalapally Ramachary, Srinivasa Reddy P., Jagjeet Gujral
Powerful asymmetric desymmetrization of thiane-3,5-diones through formal [3+3]-cycloaddition with alkyl vinyl ketones has been disclosed to access functionally rich 2-thiabicyclo[3.3.1]nonanes in very good yields with excellent enantio- and diastereoselectivities by using organocatalysis.
Front Cover: Synthesis and Applicability of Base-Discriminating DNA-Triplex-Forming 19F NMR Probes (Eur. J. Org. Chem. /2018) Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-16 Naresh Bhuma, Ville Tähtinen, Pasi Virta
Preparation of Well-Ordered Mesoporous-Silica-Supported Ruthenium Nanoparticles for Highly Selective Reduction of Functionalized Nitroarenes through Transfer Hydrogenation Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-16 Ning Wei, Xiujing Zou, Haigen Huang, Xueguang Wang, Weizhong Ding, Xionggang Lu
A novel synthetic route to heteroanthracenes Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-15 Sergey Ilyasov
This is the first report describing the synthesis of 2,3,4а,6,7,8а,9,10-octaaza-4,8-dioxo-3,4,4a,7,8,8а,9,9a,10,10а-decahydroanthracene, the representative of octaaza derivatives of reduced anthracene, by reacting glyoxal bis(nitrosemicarbazone) with glyoxal bis(hydrazone) in aqueous medium upon heating at 70°C as well as by hydrolytic decomposition of glyoxal bis(nitrosemicarbazone) in aqueous medium at 70°C via one-pot transformation. The structure of the resultant compound was confirmed by physicochemical analytical methods and X-ray diffraction. Here we also obtained the first representative of the cyclic monohydrazone dimer, 1,2,4,5,8,9,11,12-octaazacyclotetradeca-5,7,12,14-tetraene-3,10-dione existing as lactam and lactim tautomers, by reacting glyoxal bis(nitrosemicarbazone) with glyoxal bis(hydrazone) in aqueous alkaline medium upon heating.
Blue-fluorescent probes for lipid droplets based on dihydrochromeno- pyrazolepyridine and pyrrolopyridine Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-12 Martin Becerra-Ruiz, Victor Vargas, Patricio Gregorio Jara, Cristian Tirapegui, Carlos Carrasco, Marco Tulio Núñez, Nicolas Lezana, Antonio Galdámez, Marcelo Vilches Herrera
Lipid droplets (LDs) have been recognized as highly dynamic cellular organelles involved in important biological functions for the survival of organisms such as supplying food or energy. Nevertheless, lipid storage must be tightly controlled, since both its excess and the inability to store lipids can be detrimental to the organism, resulting in metabolic diseases or multifaceted systemic problems. Visualization and monitoring the concentration of LDs is essential to understand these processes. Commercially available LD dyes such as nile red and BODIPY offer several advantageous characteristics but can be limiting in multicolor imaging since most ready-made fluorescent reporter constructs fluoresce in the green to red region of the visible spectrum. Nile red emits between green and red, and BODIPY can be photoconvertable from green to red fluorescent, limiting its ability to utilize it for time lapse imaging of living cells. Here, we report the design and synthesis, the photophysical characterization, and biological results with two easily prepared series of new blue fluorescing dyes as markers for LDs. Confocal fluorescence microscopy results show an interesting correlation between the chemical structure of these fluorescent probes and the specific staining pattern. The pyrazole-based structure (6c) is specific for LDs, whereas the pyrrole-based structure (5d) resulted in prominent dyeing of the membranous cell organelles.
Synthesis of Trifluoroacetyl-Substituted Cyclopropanes Using Onium Ylides Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-12 Michael Winter, Christina Gaunersdorfer, Lukas Roiser, Katharina Zielke, Uwe Monkowius, Mario Waser
The use of carbonyl-stabilized ammonium- and sulfonium ylides allows for the synthesis of highly-functionalized trifluoroacetyl-substituted cyclopropanes. It turned out that the diastereoselectivities strongly depend on the nature of the chosen ylide and the employed base. The products could be obtained in good yields under operationally simple conditions.
Synthesis, cytotoxicity evaluation in human cell lines and in vitro DNA interaction of a hetero arylidene-9(10H)-anthrone Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-12 Paula S. Branco, Daniela Peixoto, Margarida Figueiredo, Gabriela Malta, Catarina Roma-Rodrigues, Pedro Viana Batista, Alexandra R. Fernandes, Sónia Barroso, Ana Luisa Carvalho, Carlos A. M. Afonso, Luísa Maria Ferreira
A new and never yet reported hetero arylidene-9(10H)-anthrone structure (4) was unexpectedly isolated on reaction of 1,2-dimethyl-3-ethylimidazolium iodide (2) and 9-anthracenecarboxaldehyde (3) under basic conditions. Its structure was unequivocally attributed by X-ray crystallography. No cytotoxicity in human healthy fibroblasts and in two different cancer cell lines was observed indicating its applicability in biological systems. Compound 4 interacts with CT-DNA by intercalation between the adjacent base pairs of DNA with a high binding affinity (Kb = 2.0(± 0.20) x 105 M-1) which is 10x higher than that described for doxorubicin (Kb = 3.2 (±0.23) × 104 M-1). Furthermore, compound 4 quenches the fluorescence emission of GelRed-CT-DNA system with a quenching constant (KSV) of 3.3(±0.3) x 103 M-1 calculated by the Stern-Volmer equation.
Fluorescent Recognition of 1,3-Diaminopropane in the Fluorous Phase: Greatly Enhanced Sensitivity and Selectivity Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-11 Dan Shi, Xinjing Wang, Shanshan Yu, Feng Zhao, Yachen Wang, Jun Tian, Lingling Hu, Xiaoqi Yu, Lin Pu
A 1,1'-binaphthyl-based dialdehyde soluble in the fluorous phase is synthesized. It is discovered that the fluorescence of this compound (2) can be greatly enhanced by 1,3-diaminopropane (DAP) in perfluorohexane (FC-72) but not by other amines and diamines. Thus, this compound can be used as a fluorescent sensor for the detection of the biologically important DAP at submicromolar concentrations. It is also found that the selectivity and sensitivity of this fluorescent probe in the fluorous solvent are much greater than those in a common organic solvent such as methylene chloride.
Synthesis of Triazolium Inner Salts by Thiocyanation of Aldehyde-Derived Hydrazones Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-11 Alakananda Hajra, Susmita Mondal, Sadhanendu Samanta
Ammonium persulphate mediated thiocyanation of aldehyde-derived hydrazone has been carried out to afford 5-thioxo-1,2,4-triazolium inner salt under metal-free conditions at ambient temperature. A library of triazolium inner salts were synthesized with broad functionalities in high yields. The reaction proceeds through thiocyanation followed by isomerization to isothiocyanate and cyclization.
Immobilization of UDP-galactose on an amphiphilic resin Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-11 Jessica G. M. Bevan, Eva C Lourenço, Miguel Chaves-Ferreira, João Rodrigues, Maria Rita Ventura
Nucleotide sugars are activated sugar precursors used by glycosyltransferases to form glycans. Here we report the first examples of resin-bound nucleotide sugars: fluorinated UDP-galactose and UDP-galactose. They were conjugated to a polyethylene glycol resin via the C6 position with an SMCC linker in good to excellent yields. This synthesis represents an efficient method to access resin-bound nucleotide sugars in a modular approach that enables modifications of the sugar or nucleotide before conjugation. The system has been conceived as a new chemistry-based screening system for enzymes that use UDP-galactose.
Chemoselective Synthesis of Arylpyridines via Suzuki-Miyaura Cross-Coupling Reactions Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-11 Rodisnel Perdomo Rivera, Peter Ehlers, Lars Ohlendorf, Eugenio Torres Rodriguez, Alexander Villinger, Peter Langer
4-Bromo-2,3,5-trichloro-6-iodopyridine has been synthesized for the first time and applied in chemo- and site-selective Suzuki-Miyaura cross-coupling reactions. This novel starting material allows the selective synthesis of pentaarylpyridines with up to four different aryl substituents.
Recent Advances in Palladium-Catalyzed Carboxylation with CO2 Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-11 Jian Song, Qing Liu, Hui Liu, Xuefeng Jiang
Domino Reaction of Naphthoquinone and β-Arylpyruvic Acids: Synthesis of 3-(Naphthoquinonyl)naphthofuran-2(3H)-ones Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-10 Maria Ribagorda, Carmen Carreño, Laura Ortiz-Rojano, Mario Martinez-Mingo, Carolina Garcia-Garcia
An unprecedented reactivity between naphthoquinone and β-aryl-α-keto acids has been uncovered. The process combined the redox properties of the Michael-type naphthoquinone acceptor with arylpyruvic acid, which is acting first as a C3-donor pro-nucleophile and later as an acylating agent. As a result, densely substituted naphthofuran-2(3H)-ones were generated in a mild and simple one-pot reaction
2H-[1,3]Oxazino[3,2-a]indolin-4(3H)-ones: A New Class Of Polyheterocyclic Indole-based Compounds Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-10 Jan Hartmann, Marita de Groot, Katja Schäringer, Kira Henke, Kari Rissanen, Markus Albrecht
A methodology for the synthesis of 2H-[1,3]oxazino[3,2-α]indolin-4(3H)-ones is reported. They are obtained from readily available materials by a facile synthetic procedure following either a two step cascade reaction or a step by step transformation. The target compounds represent a hitherto unreported class of indole derivatives with a novel kind of tris- or tetracyclic backbone.
Metal-Free N-H/C-H Coupling for Efficient Synthesis of Chiral Dihydroquinoxalinones From Readily Available α-Amino Acids Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-10 Kyalo Stephen Kanyiva, Masashi Horiuchi, Takanori Shibata
We have developed a method for the synthesis of dihydroquinoxalinones via intramolecular N-H/C-H coupling using hypervalent iodine. The starting materials were prepared from inexpensive and readily available aniline and amino acid derivatives. Various functional groups were tolerated to give multisubstituted dihydroquinoxalinones in moderate to excellent yields. The chirality of the amino acid was transferred to the desired target compound without a loss of enantiomeric excess. Preliminary mechanistic studies indicated that the reaction proceeds via an ionic mechanism.
Divergent Synthesis of Bioactive Marine Meroterpenoids via Palladium-Catalyzed Tandem Carbene Migratory Insertion Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-09 Yan-Chao Wu, Hong-Shuang Wang, Hui-Jing Li, Zhen-Guo Zhang
Divergent synthesis of (+)-8-epi-puupehedione, (+)-chromazonarol, (+)-yahazunol and (+)-yahazunone has been accomplished by using a palladium-catalyzed tandem carbene migratory insertion of an aryl iodine and a drimanal hydrazone, a highly regioselective reduction of enols, an oxa-Stork-Danheiser transposition reaction, an electrocyclization cyclization of a conjugated tetraenone, and a redox reaction of dimethoxybenzenes as the key steps.
High-Efficiency Catalytic Oxidation of Inert C(sp3)−H Bond Functionalization with Oxygen by Synergetic Cu NPs/N-Doped Graphene Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-09 Wei Sun, Lingfeng Gao, Xue Feng, Xu Sun, Gengxiu Zheng
The applicability of Cu is still limited in heterogeneous catalytic oxidation of C(sp3)−H bond functionalization. The problem could be resolved by synergistic effect of Cu nanoparticles (Cu NPs) and N-doped graphene. We demonstrated a high-efficient green protocol for catalytic oxidation of inert C(sp3)−H bond functionalization only with oxygen as the oxidant by Cu NPs/N-doped graphene (Cu-N-rGO). The new composite materials were obtained through a very simple one-pot solvothermal process. Remarkably, the newly-prepared Cu-N-rGO shown 34.5% conversion and 89.2% selectivity for the catalytic oxidation of cyclohexane to KA oil in a single cycle, exhibited a significantly higher efficiency than the N-free Cu catalysts. The Cu-N-rGO possessed good stability because of the doped nitrogen-atoms leads to a strong interaction between the Cu species and graphene, so that the conversion and selectivity maintained well after 5 runs in the oxidation reaction. The delicate relationship of Cu NPs and nitrogen has been investigated by accurately control the ratio of the nitrogen and Cu in the doped graphene. The hypothesis of a free radical chain mechanism and per-oxidative oxidation process has been proved and explained, and the synergistic effect of Cu NPs and N-doped graphene on facilitating the oxidation process also has been elucidated.
Syntheses and Photophysical Properties of Dibenzobarrelene-Incorporated 1,4-Diphenyl-1,3-pentadiene and Its 5-Sila Derivatives Having High Fluorescence Efficiency Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-09 Akihiko Ishii, Mari Shibata, Ryota Ebina, Norio Nakata
Dibenzobarrelene-incorporated 1,3-pentadiene and its 5-sila derivatives were synthesized by intramolecular cycloadditions between (9-anthryl)methyl, (9-anthryl)hydroxymethyl, or (9-anthryl)dimethylsilyl groups and a phenylethynyl group connected by an ethene moiety with the cis-form. The three compounds luminesced blue (λem = 432-445 nm) in CH2Cl2 with high quantum yields (ΦF = 0.83-0.92). In the solid state, the methylene and dimethylsilyl compounds luminesced (λem = 442 and 438 nm, respectively) with narrow full-width at half-maxima (FWHM) (40 and 37 nm, respectively), while the hydroxymethylene compound showed a broad and slightly red-shifted emission (λem = 488 nm, FWHM = 112 nm) due to intermolecular hydrogen bonding. The fluorescence intensity of the dimethylsilyl compound was decreased by desilylation with Bu4NF. Their structures were characterized unambiguously by NMR spectroscopy and X-ray crystallography, and their photophysical properties were elucidated experimentally together with TD-DFT calculations.
Front Cover: Directed ortho-Metalation of O-Aryl N,N-Dialkylcarbamates: Methodology, Anionic ortho-Fries Rearrangement, and Lateral Metalation (Eur. J. Org. Chem. /2018) Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-10 M. A. Jalil Miah, Mukund P. Sibi, S. Chattopadhyay, Oluwole B. Familoni, Victor Snieckus
Cover Feature: Copper-Catalyzed Carbonyl Group Controlled Coupling of Isatin Oximes with Arylboronic Acids To Prepare N-Aryloxindole Nitrones (Eur. J. Org. Chem. /2018) Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-10 Xue-Ling Mo, Chun-Hua Chen, Cui Liang, Dong-Liang Mo
Molecular Transformation of 2-Methylazulenes: An Efficient and Practical Synthesis of 2-Formyl- and 2-Ethynylazulenes Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-09 Taku Shoji, Takanori Araki, Nanami Iida, Yoshiaki Kobayashi, Akira Ohta, Ryuta Sekiguchi, Shunji Ito, Shigeki Mori, Tetsuo Okujima, Masafumi Yasunami
2-Formylazulene derivatives were obtained in good yields by the reaction of 2-methylazulenes with N,N-dimethylformamide dimethyl acetal, followed by oxidative cleavage of intermediately formed enamines with NaIO4. Vilsmeier formylation of 1-phenyl-3-methylazulenes also afforded the corresponding 2-formylazulenes in moderate yields. In a 2-methylazulene derivative having a formyl group at the 1-position, self-condensation reaction was also observed by the treatment with sodium methoxide to produce a trans-1-(azulen-1-yl)-2-(azulen-2-yl)ethylene derivative, of which structure was clarified by single crystal X-ray analysis. 2-Formylazulenes obtained by the reaction were also transformed to 2-ethynylazulenes in good yields by modified Seyferth−Gilbert reaction. The reactivity of 1-iodoazulene bearing 2-formyl function toward palladium-catalyzed cross-coupling reactions was also examined.
Construction of 4-Isochromanones via Cu(OTf)2-Catalyzed Sequential C=O and C-O Bond Formations Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-08 Siyang Xing, Nan Gu, Jiajing Qin, Hong Cui, Yan Li, Kui Wang, Dawei Tian, Bo Chen, Guo Yu
A new strategy for the facile and efficient synthesis of 4-isochromanones has been developed via a Cu(OTf)2-catalyzed sequential reaction of epoxides carrying electron-deficient alkenes using the solvent DMSO as the oxidant. The single-step process involves a sequential oxidative ring opening of epoxides and oxa-Michael addition where one new C=O bond and one new C-O bond were created. The advantages of this methodology include high bonding efficiency, a broad substrate scope and mild conditions.
Stereocontrolled cascade cyclisation of campholenic enol-ether derivatives: en route to vetiver-scented spiroxides Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-08 Pierrick Ondet, Jean-Jacques FILIPPI, Gilles Lemière, Elisabet Dunach
The Lewis superacid-catalysed cascade cyclisation of enol-ethers derived from campholenal resulted in an elegant reaction leading to new elaborated spirocyclic ethers. Under identical conditions, the reaction underwent two distinct mechanisms, depending on the relative configuration of the starting substrate. Hence, either a tandem cyclisation process gave access to tetracyclic spirodiethers, while another process involving a less common reaction sequence (cyclisation/1,4-hydride shift) led to complex tricyclic spiroalcohols and/or spiroketones. Investigations on synthetic intermediates by enantioselective gas chromatography permitted to assess the high stereospecificity of the process. Collectively, these expedite syntheses gave access to unprecedented spiroxides which displayed, in some instances, strong vetiver-like olfactory notes. While campholenic derivatives have long been used in the industrial production of fragrant sandalwood substitutes, these new derivatives provide potential synthetic alternatives to the esteemed natural ingredient vetiver.
Radical-mediated formal C(sp2)-H functionalization of aldehyde-derived N,N-dialkylhydrazones Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-08 Alexis Prieto, Didier Bouyssi, Nuno Monteiro
Recent advances in formal C(sp2)-H functionalization of aldehyde-derived N,N-dialkylhydrazones (substitution at azomethine carbon atom) are highlighted with a focus on radical-mediated processes that open up new opportunities for C-C bond formation such as alkylation reactions using hypervalent iodonium reagents or polyhaloalkanes, as well as for carbon-heteroatom bond formation (C-N, C-P). Cascade sequences based on these reactions, and leading to (hetero)cyclic frameworks, are also discussed.
Highly Diastereo- and Enantioselective Cascade Synthesis of Bicyclic Lactams in One-pot Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-07 Armando Cordova, Yan Jiang, Luca Deiana, Rana Alimohammadzadhe, Leifeng Liu, Junliang Sun
A versatile and highly stereoselective synthetic route to functionalized bi- and tricyclic lactams (up to >20:1 dr and 99% ee) in one-pot from simple starting materials (allylic alcohols, enals, diamines and aminoalcohols) using cascade transformations promoted by chiral amine/Brønsted or metal/chiral amine/Brønsted relay catalysis is disclosed. Here molecular oxygen is employed as the terminal oxidant for the latter relay catalysis approach.
Synthesis of a Thiophene Analogue of Isoindigo via C-H Activation/Oxidative Cyclization and Application of Its Copolymeric Materials to Organic Transistors Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-06 Hua-Chun Wang, Jingwei Tao, Wei-Yun Bai, Zi-Yi Xie, Xiancheng Ren, Hongxiang Li, Yun-Xiang Xu
A novel synthetic method of a thiophene analogue of isoindigo (TIIG) is described. The reaction is implemented through palladium-catalyzed C-H activation/oxidative cyclization process. This new methodology has potential for the expansion of isoindigo family. The thin film transistors (TFTs) of TIIG-based copolymer (PIDTT-TIIG) with indacenodithieno[3,2-b]thiophene (IDTT) as donor part exhibited hole mobilities of 0.17 cm2 V−1 s−1.
Purified mCPBA, a useful reagent for the oxidation of aldehydes Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-05 Alexander Horn, Uli Kazmaier
Purified mCPBA is an useful reagent for the oxidation of several classes of aldehyde. While linear unbranched aliphatic aldehydes are oxidized to the corresponding carboxylic acids, α-branched ones undergo BV oxidation to formates. α-Branched α,ß-unsaturated aldehydes provide enolformates and/or the epoxides thereof, which can be saponified to α-hydroxy ketones with an shortening of the carbon chain by 1 carbon. Unbranched α,ß-unsaturated aldehydes undergo an interesting BV oxidation / epoxidation / formate migration / BV oxidation cascade, resulting in formyl-protected hydrates with an overall loss of two carbon atoms.
Total Synthesis of Two 8-Oxoprotoberberine Alkaloids: Alangiumkaloids A and B Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-05 Takashi Nishiyama, Miharu Hironaka, Mizuki Taketomi, Eri Taguchi, Rika Kotouge, Yoshiyuki Shigemori, Noriyuki Hatae, Minoru Ishikura, Tominari Choshi
A new and versatile synthetic route for 8-oxoprotoberberine 17 via the synthesis of isoquinolinone 16 and construction of a B-ring is described. The key step is the synthesis of isoquinolinone 14 through thermal cyclization of 2-alkynylbenzaldehyde oxime 12 to afford isoquinoline N-oxide 13, followed by a Reissert-Henze-type reaction. The first total synthesis of 8-oxoprotoberberine alkaloid alangiumkaloids A and B was achieved by using this strategy.
A TBPB Mediated C-3 Cycloalkylation and Formamidation of 4-Arylcoumarin Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-04 Bhisma Kumar Patel, Sarangthem Joychandra Singh, Bilal Ahmad Mir
A tert-butyl peroxybenzoate (TBPB) mediated cycloalkylation and formamidation took place effectively in chlorobenzene or in respective formamides at 120 oC, while the former process requires the presence of acetic acid, the later goes in its absence. This radical mediated process gives moderate to good yields of the product having broad substrate scope.
Understanding the Reactivity of Fullerenes through the Activation Strain Model Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-04 Israel Fernandez
The Activation Strain Model of reactivity constitutes nowadays a powerful tool to quantitatively understand and also design chemical reactions. This approach, combined with the Energy Decomposition Analysis method, has been really helpful to our current understanding of different fundamental transformations in chemistry. In this Microreview, we illustrate the usefulness of this methodology to gain more insight into the chemistry of fullerenes. To this end, representative recent applications, which span from the regioselectivity in Diels-Alder cycloaddition reactions to the reactivity of endohedral fullerenes, are presented.
One-pot Synthesis of Highly Substituted Pyrroles via Three Component Reactions of Donor-Acceptor Cyclopropanes, Salicylaldehydes and Ammonium Acetate Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-04 Zhenjie Su, Wenxing Gu, Siran Qian, Shuwen Xue, Cunde Wang
An efficient and one-pot synthesis of highly substituted pyrroles from donor-acceptor cyclopropanes, salicylaldehydes and ammonium acetate was developed. This reaction involves a domino sequence consisting of ring opening of donor-acceptor cyclopropanes, [3 + 2] annulation reaction and aromatization as key unit steps. The elegant methodology afforded functionalized pyrroles with easy operation under mild reaction conditions and with wide substrate scope.
The Mysticism of Pericyclic Reactions. A Contemporary Rationalisation of Organic Reactivity Based on Electron Density Analysis. Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-04 luis R. Domingo, Mar Ríos-Gutiérrez, Bernard Silvi, Patricia Pérez
The molecular mechanism of the five most representative "pericyclic reactions" has been studied applying the Molecular Electron Density Theory (MEDT). The different phases in which the reaction paths are topologically divided can be regrouped into four well characterised groups: (i) rupture of the C-C double bonds; (ii) formation of the pseudoradical centers at the interacting carbons; (iii) formation of the new CC single bonds; and (iv) formation of the new C-C double bonds in the final products. Consequently, the bonding changes in these reactions are neither concerted nor cyclic. As the transition state structures are located at the end of the large first group or in the narrow second group, the high activation enthalpies found in these reactions are mainly associated to the rupture of the C-C double bonds. The present MEDT study makes it possible to rule out the definition of "pericyclic reactions", made by Woodward and Hoffmann in 1969, in which "all first order changes in bonding relationships take place in concert on a closed curve".
Enantioselective Direct Synthesis of syn- and anti-α,β-Dihydroxy γ-Ketoesters by a Dinuclear Zinc-AzePhenol Complex Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-03 Zhao-Fei Zhang, Xiao-Chao Yang, Hui-Jie Lu, Min-Can Wang
A one-step enantioselective direct synthesis of both syn- and anti-α,β-dihydroxy γ-ketoesters by a dinuclear zinc-AzePhenol complex is presented. This asymmetric α-hydroxyacetate aldol reaction proceeds in moderate to good yield and with excellent enantioselectivity of up to 99% ee. The desired products could be versatile intermediates for several transformations.
Reactions of 1-Arylbenziodoxolones with Azide Anion: Experimental and Computational Study of Substituent Effects Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-03 Mekhman Yusubov, Natalia Soldatova, Pavel Postnikov, Rashid Valiev, Dmitry Svitich, Roza Yusubova, Akira Yoshimura, Thomas Wirth, Viktor Zhdankin
New substituted 1-arylbenziodoxolones were prepared and their reactivity with azide anion nucleophile was investigated. It was found that independent on the presence of substituents, all reactions of 1-arylbenziodoxolones proceed as nucleophilic substitution of the iodonium leaving group in the electron-deficient benziodoxolone benzene ring. The presence of bulky substituents in the ortho-position of the aryl ring slowers the reaction, while the presence of a moderately electron-withdrawing bromine substituent in the para-position to iodine in the benziodoxolone ring moderately increases the rate of substitution. The presence of a strongly electron-withdrawing nitro group in the para-position to iodine in the benziodoxolone ring dramatically increases the rate of substitution. These observations are in agreement with the electronic requirements for internal nucleophilic substitution in the benziodoxole ring. A quantum-chemical computational study of the possible reaction paths is in agreement with the observed effects of substituents on the reactivity of arylbenziodoxolones in this reaction.
A One - Pot Cascade Reaction Combining NH-sulfoximines with thiophenols under mild conditions Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-03 Yong Wu, Yao Peng, Yan Lin, Ruifang Nie, Yang Zheng, Yanzhao Liu, Li Guo
A general protocol for the N-thioetherification of NH-sulfoximines was developed. Catalyzed by [Cu(DMAP)4I]I, N-sulfenyl sulfoximines were synthesized by a one-pot cascade reaction using commercially available thiophenols as the sulfur sources at room temperature. The protocol we described was found to be react mild and operationally simple, afforded the corresponding products with good yields and excellent tolerance of the functional groups.
Asymmetric Sulfinylations of N-Methylephedrine-Modified Tri- or Tetraalkyl Zincates by Symmetric Diaryl Sulfoxides Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-03 Reinhard Brückner, Simon Ruppenthal
Diethylzinc was treated with 1 or 2 equiv. of AlkMgCl or PhMgBr (preferably) or with 1 equiv. of nBuLi (less efficiently) for forming species - plausibly zincates - which were sulfinylated by diaryl sulfoxides to give racemic alkyl aryl sulfoxides in yields reaching 100%. Dialkylzinc reagents were also activated by treatments with 1 or 2 equiv. of an enantiomerically pure alkylmagnesium beta-aminoalkoxide. This worked best when the alkoxide stemmed from a dialkylmagnesium reagent and an equimolar amount of N-methyl-(-)-ephedrine. This second activation mode allowed sulfinylations of what was originally the dialkylzinc reagent with diaryl sulfoxides. This generated alkyl aryl sulfoxides with enantiomeric ratios up to 93:7 in up to 100% yield.
Bambusurils Bearing Nitro Groups and Their Further Modifications Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-03 Mirza Arfan Yawer, Kristina Sleziakova, Lukas Pavlovec, Vladimir Sindelar
Benzopyrano-fused N-heterocyclic Polyaromatics Eur. J. Org. Chem. (IF 2.834) Pub Date : 2018-01-02 Sven Elbert, Frank Rominger, Martin Reinschmidt, Kevin Baumgärtner, Michael Mastalerz
Polycyclic heteroaromatic compounds are potentially interesting materials for organic electronics application. While most of those structures compounds contain nitrogen or sulfur, oxygen-based structures are much rarer, especially those including annulated pyrane rings. By the utilization of a cascade of Pictet-Spengler reactions and thermally induced ipso-substitution, a series of peri-benzopyrano-fused nitrogen containing polycyclic aromatic compounds was synthesized and their optoelectronic properties investigated by UV/Vis- and emission spectroscopy as well as cyclovoltametry and DFT-calculations.
Rhodium-Catalyzed Ortho-Cyanation of 2-Aryl-1,2,3-triazole : An alternative Approach to Suvorexant Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-31 Hailong Zhang, Li Jing, Yang Zheng, Rui Sang, Yi Zhao, Qiantao Wang, Yong Wu
A rhodium-catalyzed ortho-cyanation of 2-aryl-1,2,3-triazole has been developed employing N-cyano-N-phenyl-p-toluensulfonamide (NCTS) as an environmentally friendly cyanide source. This simple cyanation reaction provides a new protocol for the diversification of benzonitriles in moderate to good yields and tolerates useful functional groups. Additionally, the method could also be used to synthesize 5-methyl-2-(2H-1,2,3-triazol-2-yl)benzoic acid, which is the key intermediate of suvorexant.
One-pot Allan-Robinson/Friedländer route to Chromen-/Quinolin-4-one via Domino Acetylative Cyclisation of 2-Hydroxy-/2-Aminobenzaldehyde Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-30 Vijai Kumar Rai, Manorama Singh, Ankita Rai, Fooleswar Verma, Ganeswar P. Sahu
Domino synthesis of 2-phenyl-4H-chromen-4-ones and quinolin-4-ones via acetylation of 2-hydroxy/-2-aminobenzaldehyde with α-haloketones followed by intramolecular oxa-/azaheterocyclization is reported. The envisaged method is novel extension of Allan-Robinson and Friedländer reaction using N-heterocyclic carbene catalysis to construct target molecules in good to excellent yield; 86-95% of chromen-4-ones and 83-96% of quinolin-4-ones and has advantage of its operational simplicity, no by-product formation, and ambient reaction conditions.
Base-Promoted Sulfur-Mediated Carbonylative Cyclization of Propargylic Amines Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-29 Jun Ying, Hai Wang, Xinxin Qi, Jin-Bao Peng, Xiao-Feng Wu
A tBuOK mediated carbonylative cyclization of propargylic amines with elemental sulfur has been developed. With benzene-1,3,5-triyl triformate (TFBen) as a convenient CO surrogate, various substituted 1,3-thiazolidin-2-ones were produced in good to excellent yields.
Front Cover: Fluoride-Catalyzed Nucleophilic Addition of PhSCF2SiMe3 to Isatins: Synthesis of 3-(1′,1′-Difluoroalkyl)-3-hydroxyindolin-2-ones (Eur. J. Org. Chem. /2018) Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-29 Sirisuk Keereewan, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul, Manat Pohmakotr
Front Cover: Enantioselective Synthesis of the C23–C33 Fragment of Aetheramide A and Its C32 Epimer (Eur. J. Org. Chem. /2018) Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-29 Tibor Peňaška, Petr Koukal, Martin Kotora
Simple Synthesis of Phytochemicals by Heterogeneous Pd- and Ir-Catalyzed Hydrogen-Borrowing C–C Bond Formation Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-29 Yoji Hori, Chiharu Suruga, Yuta Akabayashi, Tomoka Ishikawa, Marina Saito, Takao Myoda, Kazuki Toeda, Yuna Maeda, Yutaka Yoshida
Pd-Catalyzed P‒C Cross-Coupling of Aryl Bromides and Triflates with Hydroxymethylphosphine Sulfide Derivatives Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-28 Hidetoshi Ohta, Qian Xue, Minoru Hayashi
The development of a versatile process for phosphine synthesis has attracted considerable interest because organophosphines are indispensable for organic synthesis. Previously, we developed a Pd-catalyzed P‒C coupling reaction for hydroxymethylphosphine sulfide derivatives with various aryl iodides as a method for preparing a variety of triarylphosphine derivatives. However, the catalyst system for aryl iodides did not activate aryl bromides and triflates, which are more readily available than aryl iodides. Herein, we report a new and effective catalyst system for the P‒C coupling of various aryl bromides and triflates with hydroxymethylphosphine sulfides. An application of the new method was demonstrated with the sequential synthesis of an unsymmetrically substituted triarylphosphine sulfide using multiple couplings of an orthogonally protected precursor.
Synthesis of α,α-dichloroketones through sequential reaction of decarboxylative coupling and chlorination Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-28 Sunwoo Lee, Eunjeong Cho, Myungjin Kim, Aravindan Jayaraman, Jimin Kim
2,2-Dichloro-1,2-diarylethanones were synthesized via the reaction between an alkyne and trichloroisocyanuric acid. The reaction was conducted in CH3CN-H2O at room temperature for 12 h. In addition, the desired 2,2-dichloro-1,2-diarylethanones could be prepared from aryl bromides and propiolic acid through sequential of Pd-catalyzed decarboxylative coupling and chlorination. This method showed moderate to good yields and good tolerance toward functional groups such as chlorides, bromides, aldehydes, and ketones.
Synthesis of the aglycon of the antibiotic disciformycin Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-28 Andreas Kirschning, Michael Wolling
Abstract: The synthesis of the aglycon of disciformycin, a new secondary metabolite from Pyxidicoccus fallax, is reported. The disciformycins are highly potent antibiotics including inhibitory activity towards methicillin- and vancomycin-resistant Staphylococcus aureus. The stereocontrolled installation of the olefinic double bonds at C2-C3/C3-C4 and C12-C13, respectively, as well the orthogonal differentiation of the oxy functionalities turned out to be key challenges of our approach.
Pre-activation Based Stereoselective Glycosylations Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-28 Bo Yang, Weizhun Yang, Sherif Ramadan, Xuefei Huang
Due to the wide presence of carbohydrates in nature and their crucial roles in numerous important biological processes, oligosaccharides have attracted a lot of attention in synthetic organic chemistry community. Many innovative synthetic methods have been developed for oligosaccharide synthesis, among which the pre-activation based glycosylation is particularly noteworthy. Traditionally, glycosylation reactions are carried out when the glycosyl donor and the acceptor are both present when the promoter is added. In comparison, the pre-activation based glycosylation is unique, where the glycosyl donor is activated by the promoter in the absence of the acceptor. Upon complete donor activation, the acceptor is added to the reaction mixture enabling glycosylation. The key step in any oligosaccharide synthesis is the stereoselective formation of the glycosidic bond. As donor activation and acceptor glycosylation are temporally separated, pre-activation based glycosylation can bestow unique stereochemical control. This review systematically discusses factors impacting the stereochemical outcome of a pre-activation based glycosylation reaction including substituents on the glycosyl donor, reaction solvent, and additives. Applications of pre-activation based stereoselective glycosylation in assembly of complex oligosaccharides are also discussed.
Direct oxidation of cyclopropanated cyclooctanes as a synthetic approach to polycyclic cyclopropylketones Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-28 Kseniya N. Sedenkova, Kristian S. Andriasov, Svetlana A. Stepanova, Igor P. Gloriozov, Yuri Grishin, Tamara S. Kuznetsova, Elena B. Averina
A series of polycyclic hydrocarbons containing cyclopropane moieties 1,2-annelated or spiro-condensed with cyclooctane ring were investigated under oxidative conditions. Four oxidizing systems (O3 on SiO2, dioxirane derived from trifluoroacetone, CrO3 and RuO4, generated in situ), were employed to evaluate and compare their reactivity and usefulness. RuO4 was found to be the best one, considering its oxidative power together with a simple preparative procedure. The conditions for specific oxidation of polycyclic hydrocarbons were found. Novel cyclooctane derivatives containing cyclopropyl carbonyl moieties were obtained.
One-pot Alkynylation of Azaaryl Aldehydes and Spontaneous Base free Rearrangement into Enone Esters: an Autoinductive Mechanism Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-26 Bora Sieng, Matias Funes-Maldonado, Carlo Romagnoli, Mohamed Amedjkouh
A direct synthesis of γ-oxo-α,β-unsaturated esters has been developed. When heteroaromatic aldehydes are reacted with deprotonated ethyl propiolate, in the presence of Me2Zn or BuLi, the newly formed propargylic alcohol rearranged spontaneously to give the corresponding unsaturated keto-ester. Isotope labeling, allenol intermediate trapping and crossover experiments provided insight into the reactive sequence and suggest an autocatalytic mechanism.
3,4-Diaminomaleimide Dyes: Simple Luminophores with Efficient Orange-Red Emission in the Solid State Eur. J. Org. Chem. (IF 2.834) Pub Date : 2017-12-24 Hiroaki Imoto, Ryosuke Fujii, Kensuke Naka
Maleimides have been widely utilized from material science to biochemistry. Especially, maleimide-based luminescent dyes have attracted much attention. Recently we have reported arylaminomaleimide dyes exhibiting effective blue-green emission in the solid state. In this work, 3,4-diaminomaledimides were synthesized via simple and facile routes. It has been elucidated that the obtained dyes show orange-red emission due to the two amino groups. Noteworthy is that the dyes possessed very simple structures, which were composed of C, H, N, and O elements and minimal aromatic rings. Additionally, their emission intensities were enhance in the solid states, compared with those in solutions. Theoretical calculations and X-ray diffraction analyses supported understanding of the emission behaviors.
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