Copolymerization of epoxides with cyclic anhydrides catalyzed by dinuclear cobalt complexes

• Yo Hiranoi and
• Koji Nakano

Beilstein J. Org. Chem. 2018, 14, 2779–2788, doi:10.3762/bjoc.14.255

• . LLC, Tokyo Chemical Industry Co., Ltd., and Kanto Chemical Co., Inc., and were used without further purification unless otherwise specified. Commercially available anhydrous solvents were used for air and/or moisture-sensitive reactions. Epoxides for the polymerizations were dried over CaH2 and

An overview on recent advances in the synthesis of sulfonated organic materials, sulfonated silica materials, and sulfonated carbon materials and their catalytic applications in chemical processes

• Hashem Sharghi,
• Pezhman Shiri and
• Mahdi Aberi

Beilstein J. Org. Chem. 2018, 14, 2745–2770, doi:10.3762/bjoc.14.253

• isolation of products, very short reaction times (only 10 s), and better yields. The use of glycerol as a starting material is another important advantage because it is the main byproduct in the biodiesel industry and the application of renewable feedstocks for the preparation of suitable chemicals and

• reusable catalysts, due to their ability to catalyze different chemical processes in industry and laboratories. There are many reports on the carbon-based materials containing the sulfonic acid group, but the future advances of this field will depend on the better understanding of all aspects of their

Synthesis of a tyrosinase inhibitor by consecutive ethenolysis and cross-metathesis of crude cashew nutshell liquid

• Jacqueline Pollini,
• Valentina Bragoni and
• Lukas J. Gooßen

Beilstein J. Org. Chem. 2018, 14, 2737–2744, doi:10.3762/bjoc.14.252

• neurodegenerative diseases [30]. Therefore, the study and development of tyrosinase inhibitors from renewable resources is of particular interest for research and industry [31][32]. Fu et al. investigated naturally occurring ginkgolic acids which they selectively synthesized from 2,6-dihydroxybenzoic acid (4), and

Pathoblockers or antivirulence drugs as a new option for the treatment of bacterial infections

• Matthew B. Calvert,
• Varsha R. Jumde and
• Alexander Titz

Beilstein J. Org. Chem. 2018, 14, 2607–2617, doi:10.3762/bjoc.14.239

• excessive and inappropriate use of antibiotics in the commercial livestock breeding industry. Since numerous targets of classical antibiotics are conserved across a large number of bacterial species, it is obvious that resistance against antibiotics can also develop outside the patient in the environment

Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps

• Sambasivarao Kotha,
• Milind Meshram and
• Chandravathi Chakkapalli

Beilstein J. Org. Chem. 2018, 14, 2468–2481, doi:10.3762/bjoc.14.223

• and ruthenium impurities in minor amounts from the reaction mixture. This aspect is also important in the pharmaceutical industry [4][55]. Biography of the Authors Sambasivarao Kotha graduated with M.Sc. degree in Chemistry from the University of Hyderabad and obtained his Ph.D. in Organic Chemistry

A novel and practical asymmetric synthesis of eptazocine hydrobromide

• Ruipeng Li,
• Zhenren Liu,
• Liang Chen,
• Jing Pan,
• Kuaile Lin and
• Weicheng Zhou

Beilstein J. Org. Chem. 2018, 14, 2340–2347, doi:10.3762/bjoc.14.209

• Ruipeng Li Zhenren Liu Liang Chen Jing Pan Kuaile Lin Weicheng Zhou State Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R

A general and atom-efficient continuous-flow approach to prepare amines, amides and imines via reactive N-chloramines

• Katherine E. Jolley,
• Michael R. Chapman and
• A. John Blacker

Beilstein J. Org. Chem. 2018, 14, 2220–2228, doi:10.3762/bjoc.14.196

• ][33]. Improved methods for the formation of amides remain an important goal for the pharma industry. In this regard, the reaction of N-chloramine with aldehydes, t-BuO2H and iron or copper catalysts to give secondary and tertiary amides was reported in batch recently [33][34], though safety concerns

Selective formation of a zwitterion adduct and bicarbonate salt in the efficient CO₂ fixation by N-benzyl cyclic guanidine under dry and wet conditions

• Yoshiaki Yoshida,
• Naoto Aoyagi and
• Takeshi Endo

Beilstein J. Org. Chem. 2018, 14, 2204–2211, doi:10.3762/bjoc.14.194

• at room temperature and ambient moisture. Experimental General Materials and instruments All starting materials and dehydrated solvents were purchased from Wako Pure Chemical Industries (Osaka, Japan) and Tokyo Chemical Industry (Tokyo, Japan). CO2 (>99.999%, H2O < 5 ppm) was obtained from Yamagata

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• pharmaceutical industry. This type of chemistry has also demonstrated a high degree of sustainability, especially when organic dyes can be employed in place of often toxic and environmentally damaging transition metals. The sections are arranged according to the general class of the presented reactions and the

• . Examples of heterocyclic (e.g., pyridinyl) anilines would be more relevant to the pharmaceutical industry. Medicinal chemistry often requires particularly furnished hydrocarbon backbones as bioisosteric replacements. One such interesting group is the difluoromethyl group. Akita et al. have described a

• chemistry is still quite sparse in the literature. Late-stage fluorination protocols are also rare and would be exhaustively used by the pharmaceutical industry. In addition, as has been pointed out in this review

Direct electrochemical generation of organic carbonates by dehydrogenative coupling

• Tile Gieshoff,
• Vinh Trieu,
• Jan Heijl and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2018, 14, 1578–1582, doi:10.3762/bjoc.14.135

• ; dehydrogenative coupling; electrochemistry; organic carbonates; Introduction Polycarbonates are high-performance polymeric materials with versatile applications in various fields with economic impact, e.g., construction, food, and pharmaceutical industry [1]. For their technical large-scale production, organic

Cobalt–metalloid alloys for electrochemical oxidation of 5-hydroxymethylfurfural as an alternative anode reaction in lieu of oxygen evolution during water splitting

• Jonas Weidner,
• Stefan Barwe,
• Kirill Sliozberg,
• Stefan Piontek,
• Justus Masa,
• Ulf-Peter Apfel and
• Wolfgang Schuhmann

Beilstein J. Org. Chem. 2018, 14, 1436–1445, doi:10.3762/bjoc.14.121

• valuable product for the chemical industry with potential large scale use. Various cobalt–metalloid alloys (CoX; X = B, Si, P, Te, As) were investigated as potential catalysts for HMF oxidation. In this series, CoB required 180 mV less overpotential to reach a current density of 55 mA cm−2 relative to OER

• -refinery based chemicals for a “green” chemical industry [6][7][8]. FDCA was suggested to replace, e.g., terephthalic acid as building block for the formation of polyamides, polyesters, and polyurethanes [6]. Especially, the polymer polyethylene terephthalate (PET), a perpetually used polymer, could be

• Bundesministerium für Bildung und Forschung (BMBF) in the framework of the project “Mangan” (FKZ 03EK3548). U.-P. A. acknowledges financial support of the Fonds of the Chemical Industry (Liebig grant) and the Deutsche Forschungsgemeinschaft (Emmy Noether grant, AP242/2-1 and AP242/6-1).

Spectroelectrochemical studies on the effect of cations in the alkaline glycerol oxidation reaction over carbon nanotube-supported Pd nanoparticles

• Dennis Hiltrop,
• Steffen Cychy,
• Karina Elumeeva,
• Wolfgang Schuhmann and
• Martin Muhler

Beilstein J. Org. Chem. 2018, 14, 1428–1435, doi:10.3762/bjoc.14.120

• acid, mesoxalic acid and 1,3-dihydroxyacetone (DHA). These products are conventionally obtained by oxidation using rather unselective oxidants. Especially DHA is of great interest due to its use in the cosmetic industry, as a precursor for further value-added fine chemicals [9] and as a monomer for

Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine

• Ruipeng Li,
• Zhenren Liu,
• Liang Chen,
• Jing Pan and
• Weicheng Zhou

Beilstein J. Org. Chem. 2018, 14, 1421–1427, doi:10.3762/bjoc.14.119

• Ruipeng Li Zhenren Liu Liang Chen Jing Pan Weicheng Zhou State Key Lab of New Drug & Pharmaceutical Process, Shanghai Key Lab of Anti-Infectives, Shanghai Institute of Pharmaceutical Industry, China State Institute of Pharmaceutical Industry, No. 285, Gebaini Rd., Shanghai 201203, P. R. of China

• separated by two times of resolution with L-tartaric acid and D-tartaric acid (Scheme 1). Phase-transfer asymmetric catalysis with cinchona alkaloid-derived quaternary ammonium compounds has become one of the topics in stereoselective synthesis in both industry and academia [6][7][8][9]. It was reported [10

A survey of chiral hypervalent iodine reagents in asymmetric synthesis

• Soumen Ghosh,
• Suman Pradhan and
• Indranil Chatterjee

Beilstein J. Org. Chem. 2018, 14, 1244–1262, doi:10.3762/bjoc.14.107

• challenging and application-oriented conversions that can be applied for the total synthesis of natural products as well as in industry related to pharmaceutical and medicinal chemistry. These environmentally friendly, cheap and readily available reagents will surely attract the attention of scientists

Synthesis of pyrazolopyrimidinones using a “one-pot” approach under microwave irradiation

• Mark Kelada,
• John M. D. Walsh,
• Robert W. Devine,
• Patrick McArdle and
• John C. Stephens

Beilstein J. Org. Chem. 2018, 14, 1222–1228, doi:10.3762/bjoc.14.104

• the pyrazolo[1,5-a]pyrimidinones, that employ one-pot syntheses and/or processes have been encouraged and have become a major focus for many synthetic chemists [11]. As such, a convenient and general method of preparing the scaffold would be of significant interest to the pharmaceutical industry

Crystal structure of the inclusion complex of cholesterol in β-cyclodextrin and molecular dynamics studies

• Elias Christoforides,
• Andreas Papaioannou and
• Kostas Bethanis

Beilstein J. Org. Chem. 2018, 14, 838–848, doi:10.3762/bjoc.14.69

• complexes by entrapping a wide range of guest molecules into its internal hydrophobic cavity. It is non-toxic, non-irritating, edible, chemically stable, easy separable and widely used in pharmaceutical, food and chemical industry [4]. Two major cyclodextrin applications dictate a meticulous study of their

• reduced toxicity. In food industry β-CD has been used in many applications such as flavor protection and flavor delivery, controlled release of desired constituents and removal and masking of undesirable components [16]. But the most prevalent use of CD in this field is the removal of cholesterol from

Nanoreactors for green catalysis

• M. Teresa De Martino,
• Loai K. E. A. Abdelmohsen,
• Floris P. J. T. Rutjes and
• Jan C. M. van Hest

Beilstein J. Org. Chem. 2018, 14, 716–733, doi:10.3762/bjoc.14.61

• concept of green chemistry has been recently defined to guide chemists towards minimizing any harmful outcome of chemical processes in either industry or research. Towards greener reactions, scientists have developed various approaches in order to decrease environmental risks while attaining chemical

• . Unfortunately, most organic compounds and catalysts are not soluble in water, limiting its utility for most reactions [9][10]. For this reason, scientists across academia and industry have proposed many solutions in order to maximize the outcome of reactions (i.e., yields, enantioselectivities, etc.) in water

• synthetic chemistry [24][31]. In a recent study the E-factors for different traditional coupling reactions used in the pharmaceutical industry were reported and compared to those achieved in micellar nanoreactors [45], showing for the latter a decrease of at least an order of magnitude, which underlines

Biocatalytic synthesis of the Green Note trans-2-hexenal in a continuous-flow microreactor

• Morten M. C. H. van Schie,
• Tiago Pedroso de Almeida,
• Gabriele Laudadio,
• Florian Tieves,
• Elena Fernández-Fueyo,
• Timothy Noël,
• Isabel W. C. E. Arends and
• Frank Hollmann

Beilstein J. Org. Chem. 2018, 14, 697–703, doi:10.3762/bjoc.14.58

• ; alcohol oxidation; aldehyde; flow chemistry; Introduction trans-2-Hexenal is well-known as a major component of the Green Notes of fruits and vegetables such as apples, strawberries, cherries and more. It is widely used in the flavour and fragrance industry as fresh flavour ingredient in foods and

Diastereoselective auxiliary- and catalyst-controlled intramolecular aza-Michael reaction for the elaboration of enantioenriched 3-substituted isoindolinones. Application to the synthesis of a new pazinaclone analogue

• Romain Sallio,
• Stéphane Lebrun,
• Frédéric Capet,
• Francine Agbossou-Niedercorn,
• Christophe Michon and
• Eric Deniau

Beilstein J. Org. Chem. 2018, 14, 593–602, doi:10.3762/bjoc.14.46

• ][10][11]. Among the latter, optically pure compounds functionalized at C-3 by acetamido groups play an important role as key targets for the pharmaceutical industry. For example, substituted 3-isoindolinones, such as JM-1232 (II) [12][13][14] and pazinaclone (III) [15][16] (Figure 1), have shown

High-yielding continuous-flow synthesis of antimalarial drug hydroxychloroquine

• Eric Yu,
• Hari P. R. Mangunuru,
• Nakul S. Telang,
• Caleb J. Kong,
• Jenson Verghese,
• Stanley E. Gilliland III,
• Saeed Ahmad,
• Raymond N. Dominey and
• B. Frank Gupton

Beilstein J. Org. Chem. 2018, 14, 583–592, doi:10.3762/bjoc.14.45

• starting materials and reagents, simplifying the synthetic route in terms of reducing the total number of steps as well as reducing the cost and improving the efficiency of individual steps. Flow chemistry methodologies have been increasingly investigated in recent years in the pharmaceutical industry for

Electrochemical Corey–Winter reaction. Reduction of thiocarbonates in aqueous methanol media and application to the synthesis of a naturally occurring α-pyrone

• Ernesto Emmanuel López-López,
• José Alvano Pérez-Bautista,
• Fernando Sartillo-Piscil and
• Bernardo A. Frontana-Uribe

Beilstein J. Org. Chem. 2018, 14, 547–552, doi:10.3762/bjoc.14.41

• (Scheme 1) [4]. Despite this advantage, the low availability and high cost of this reagent [5] makes this reaction difficult to be used in industry. Previously, starting from the versatile chiron 7,3-lactone-xylofuranose (7,3-LXF) [6], the first non-biological synthesis of chiral 6-pentyl-2H-pyran-2-ones

An alternative to hydrogenation processes. Electrocatalytic hydrogenation of benzophenone

• Cristina Mozo Mulero,
• Alfonso Sáez,
• Jesús Iniesta and
• Vicente Montiel

Beilstein J. Org. Chem. 2018, 14, 537–546, doi:10.3762/bjoc.14.40

• ; electrocatalytic hydrogenation; palladium nanoparticles; polymer electrolyte membrane; Introduction Hydrogenation is a common procedure applied in organic chemistry industry based on the use of an external hydrogen source, generally carried out under moderate experimental conditions of high temperature (until 673

• a more complex aromatic ketone dictated by the presence of two phenyl rings, in order to analyse fractional conversion and selectivity of formed products. Here, the main obtained product is diphenylmethanol (ketone conversion to alcohol) as a high added value product in chemical industry. Even

Latest development in the synthesis of ursodeoxycholic acid (UDCA): a critical review

• Fabio Tonin and
• Isabel W. C. E. Arends

Beilstein J. Org. Chem. 2018, 14, 470–483, doi:10.3762/bjoc.14.33

• times and lower costs for the chemical and enzymatic reactions involved. Keywords: bile acids; biotransformation; hydroxysteroid dehydrogenases; production process; UDCA; Introduction Ursodeoxycholic acid (UDCA), is applied in the pharmaceutical industry (Figure 1) [1]. As reported in several papers

• industry; additional steps of purification and control of sterility are necessary to obtain a safe product for the market. Otherwise, the circumvention of protein isolation and production makes it cheaper than their free-enzyme analogues. In this way, the use of lyophilized whole-cell containing

Synthesis of fluoro-functionalized diaryl-λ³-iodonium salts and their cytotoxicity against human lymphoma U937 cells

• Prajwalita Das,
• Etsuko Tokunaga,
• Hidehiko Akiyama,
• Hiroki Doi,
• Norimichi Saito and
• Norio Shibata

Beilstein J. Org. Chem. 2018, 14, 364–372, doi:10.3762/bjoc.14.24

• of 1H, 19F and 13C NMR spectra of 7, 3p, 4b, 5a and 6a and the ORTEP diagram of 3p. Acknowledgements This research was partially supported by the Tokyo Chemical Industry Foundation, the Pesticide Science Society of Japan, and a JSPS KAKENHI Grant Number JP 16H01142 in the Middle Molecular Strategy.

Continuous-flow retro-Diels–Alder reaction: an efficient method for the preparation of pyrimidinone derivatives

• Imane Nekkaa,
• Márta Palkó,
• István M. Mándity and
• Ferenc Fülöp

Beilstein J. Org. Chem. 2018, 14, 318–324, doi:10.3762/bjoc.14.20

• addition, they are present in several natural frameworks [42][43][44]. We wanted to exploit the benefits of flow processing for reaction optimization and synthesis and develop novel sustainable synthetic methodologies with possible useful applications for the pharmaceutical industry. Our results show that