Antiviral therapy in shrimp through plant virus VLP containing VP28 dsRNA against WSSV

• Santiago Ramos-Carreño,
• Ivone Giffard-Mena,
• Jose N. Zamudio-Ocadiz,
• Alfredo Nuñez-Rivera,
• Ricardo Valencia-Yañez,
• Jaime Ruiz-Garcia,
• Maria Teresa Viana and
• Ruben D. Cadena-Nava

Beilstein J. Org. Chem. 2021, 17, 1360–1373, doi:10.3762/bjoc.17.95

• purification. The plant virus CCMV was produced in California cowpea plants (Vigna ungiculata). The plants were mechanically inoculated with a solution containing the virus. After two weeks, the infected leaves were collected and ground in a virus extraction buffer (0.5 M sodium acetate, 0.08 M magnesium

• sodium acetate, 8 mM magnesium acetate, pH 4.5). The solution was ultracentrifuged through a sucrose gradient at 30,000 rpm for 2 hours, at 4 °C. The virus was recovered from the blue band, and the sucrose was removed by ultracentrifugation. The pellets were resuspended in virus suspension buffer (50 mM

• sodium acetate, 8 mM magnesium acetate, pH 4.5). All the procedure was done at 4 °C. The virus’s concentration and purity were determined by UV–vis spectrophotometry, and the virus aliquots were kept at −80 °C. The protein purification was performed according to a previously described protocol [40

Fritsch–Buttenberg–Wiechell rearrangement of magnesium alkylidene carbenoids leading to the formation of alkynes

• Tsutomu Kimura,
• Koto Sekiguchi,
• Akane Ando and
• Aki Imafuji

Beilstein J. Org. Chem. 2021, 17, 1352–1359, doi:10.3762/bjoc.17.94

• prepared from carbonyl compounds and chloromethyl p-tolyl sulfoxide and were converted into alkynes via the sulfoxide/magnesium exchange reaction and subsequent Fritsch–Buttenberg–Wiechell (FBW) rearrangement of the resulting magnesium alkylidene carbenoids. The mechanism of the FBW rearrangement of

• magnesium alkylidene carbenoids was studied by using 13C-labeled sulfoxides and by using DFT calculations. Keywords: alkyne; 1-chlorovinyl p-tolyl sulfoxide; DFT calculation; Fritsch–Buttenberg–Wiechell rearrangement; magnesium alkylidene carbenoid; Introduction Alkynes are important compounds in organic

• with these methods, the use of butyllithium for the generation of lithium alkylidene carbenoids limits the range of usable substrates in the Corey–Fuchs method, and the Ohira–Bestmann method cannot be applied to the synthesis of internal alkynes from ketones [3]. Magnesium alkylidene carbenoids 3 are

Icilio Guareschi and his amazing “1897 reaction”

• Gian Cesare Tron,
• Alberto Minassi,
• Giovanni Sorba,
• Mara Fausone and
• Giovanni Appendino

Beilstein J. Org. Chem. 2021, 17, 1335–1351, doi:10.3762/bjoc.17.93

• carbonyl derivative. Guareschi found that the fragmentation was quantitative when an ethanolic solution of the imide was treated with magnesium hydroxide, poorly soluble but sufficient to ionize the cyanopyridone. It should be pointed out that the identification of gaseous compounds was not at all trivial

Photoinduced post-modification of graphitic carbon nitride-embedded hydrogels: synthesis of 'hydrophobic hydrogels' and pore substructuring

• Cansu Esen and
• Baris Kumru

Beilstein J. Org. Chem. 2021, 17, 1323–1334, doi:10.3762/bjoc.17.92

• % aqueous solution, Merck), magnesium chloride (MgCl2, 99%, Merck), melamine (99%, Sigma-Aldrich), poly(ethylene glycol) dimethacrylate (PEGDMA, Mn 550, Sigma-Aldrich), poly(ethylene glycol) methyl ether methacrylate (PEGMEMA, Mn 300, Sigma-Aldrich), potassium chloride (KCl, 99%, Merck), rhodamine B (RhB

• Scan spectrophotometer equipped with an integrating sphere. Thermogravimetric analysis (TGA) was performed via TG 209 Libra from Netzsch under nitrogen atmosphere with a heating rate 10 K min−1 using aluminum crucible for samples. Trace analysis of potassium, calcium and magnesium cations were

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

• process. After addition of the organomagnesium reagent to the imine 79, cyclization involving the magnesium amide and the ester occurred without the need of an extra cyclization step to give, after N-Boc protection, 4-hydroxy-5-substituted pyrrolidin-2-ones 90, with relative trans-configuration (Scheme 24

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• , glycolysis of PET was performed under microwave heating in the presence of Zn(OAc)2, yielding BHET with an 80% selectivity at 97% conversion due to formation of dimers (Table 2, entry 7) [203][204]. Soluble metal chlorides (zinc, magnesium, iron, zirconium, cobalt, nickel) were also explored as catalysts in

Designed whole-cell-catalysis-assisted synthesis of 9,11-secosterols

• Marek Kõllo,
• Marje Kasari,
• Villu Kasari,
• Tõnis Pehk,
• Ivar Järving,
• Margus Lopp,
• Arvi Jõers and
• Tõnis Kanger

Beilstein J. Org. Chem. 2021, 17, 581–588, doi:10.3762/bjoc.17.52

• ) was added, after which this was mixed and extracted with EtOAc (5 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel with gradient 7% to 30% acetone in petroleum ether to give monoacetate 3 (151 mg, 52%) and

Synthesis of (Z)-3-[amino(phenyl)methylidene]-1,3-dihydro-2H-indol-2-ones using an Eschenmoser coupling reaction

• Lukáš Marek,
• Lukáš Kolman,
• Jiří Váňa,
• Jan Svoboda and
• Jiří Hanusek

Beilstein J. Org. Chem. 2021, 17, 527–539, doi:10.3762/bjoc.17.47

• also Supporting Information File 1). The primary thiobenzamides 2a–d were prepared by the magnesium chloride-catalyzed thiolysis of commercially available benzonitriles [53] and the secondary thiobenzamides 3a–h were obtained by the thionation of the corresponding N-substituted amides [54] using

Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

• . Two different hydroxypeptide esters 46 were first prepared and successfully coupled with methyl N-Cbz-1-aminoethylphosphonochloridate ((R)-13b) by use of their magnesium salts because the direct coupling of the hydroxypeptide esters 46 with the phosphonochloridate (R)-13b failed. The magnesium salts

Ring-closing metathesis of prochiral oxaenediynes to racemic 4-alkenyl-2-alkynyl-3,6-dihydro-2H-pyrans

• Viola Kolaříková,
• Markéta Rybáčková,
• Martin Svoboda and
• Jaroslav Kvíčala

Beilstein J. Org. Chem. 2020, 16, 2757–2768, doi:10.3762/bjoc.16.226

• -diyn-4-ol (4a). The compound was prepared according to a published procedure [32] by the reaction of ethyl formate with propargylmagnesium bromide, generated from propargyl bromide (5a), magnesium and a catalytic amount of HgCl2 to suppress the formation of allenylmagnesium bromide (Scheme 5). The

Anion exchange resins in phosphate form as versatile carriers for the reactions catalyzed by nucleoside phosphorylases

• Julia N. Artsemyeva,
• Ekaterina A. Remeeva,
• Tatiana N. Buravskaya,
• Irina D. Konstantinova,
• Roman S. Esipov,
• Anatoly I. Miroshnikov,
• Natalia M. Litvinko and
• Igor A. Mikhailopulo

Beilstein J. Org. Chem. 2020, 16, 2607–2622, doi:10.3762/bjoc.16.212

• found that phosphorolysis of uridine, thymidine, and Ara-U in the presence of Dowex® 1X8 (phosphate; Dowex-nPi) proceeded smoothly in the presence of magnesium cations in water at 20–50 °C for 54–96 h giving rise to quantitative formation of the corresponding pyrimidine bases and PF-1Pis. The resulting

• reaction with Dowex-nPi resulted in slowing down of the Ara-U phosphorolysis and as a consequence nelarabine formation, and an increase in the amount of UP did not lead again to the proportional increase in nelarabine synthesis. On the contrary, the addition of magnesium ions to the reaction mixture (0.1

• of magnesium ions on metabolic transformations of nucleosides [45], in particular on the phosphorylation of the primary hydroxy group of pentoses, catalyzed by ribokinases [46], as well as on the cascade synthesis of nucleosides starting from pentoses [47][48][49][50] has been described. Based on the

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

• Si-Yuan Liu,
• Xin-Rui Wang,
• Man-Ping Li,
• Wen-Rong Xu and
• Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

• pressure and water (25 mL) was added to the mixture, which was extracted with ethyl acetate (3 × 15 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated to dryness. The crude residue obtained was purified by silica gel column chromatography (petroleum ether/ethyl

Natural dolomitic limestone-catalyzed synthesis of benzimidazoles, dihydropyrimidinones, and highly substituted pyridines under ultrasound irradiation

• Kumar Godugu,
• Venkata Divya Sri Yadala,
• Mohammad Khaja Mohinuddin Pinjari,
• Trivikram Reddy Gundala,
• Lakshmi Reddy Sanapareddy and
• Chinna Gangi Reddy Nallagondu

Beilstein J. Org. Chem. 2020, 16, 1881–1900, doi:10.3762/bjoc.16.156

• , the limited substrate scope, and complicated work-up processes; further, the products require chromatographic purification. The mineral NDL is an irregular combination of calcium and magnesium carbonate. It is water-insoluble, environmentally benevolent, inexpensive, nontoxic, and abundant in nature

One-pot and metal-free synthesis of 3-arylated-4-nitrophenols via polyfunctionalized cyclohexanones from β-nitrostyrenes

• Haruyasu Asahara,
• Minami Hiraishi and
• Nagatoshi Nishiwaki

Beilstein J. Org. Chem. 2020, 16, 1830–1836, doi:10.3762/bjoc.16.150

• water (100 mL), the pH value was adjusted to 7 with a 2 M aqueous sodium hydroxide solution. This was extracted with ethyl acetate (50 mL × 3), and the organic layer was washed with brine (100 mL × 1), dried over magnesium sulfate, and concentrated to afford crude product (2.66 g) as yellow solid. The

• × 1), dried over magnesium sulfate, and concentrated to afford the crude product (39.4 mg) as brown oil. Further purification was performed with column chromatography on silica gel to afford 3-(4-methylphenyl)-4-nitrophenol (5a) [30], which eluted with hexane/ethyl acetate 8:2 (Rf 0.44, 28.0 mg, 0.12

• 18 h, a saturated aqueous solution of sodium thiosulfate (8 mL) was added, and the mixture was extracted with ethyl acetate (8 mL × 3). The organic layer was washed with brine (8 mL × 1), dried over magnesium sulfate, and concentrated. The residue was treated by column chromatography on silica gel to

Disposable cartridge concept for the on-demand synthesis of turbo Grignards, Knochel–Hauser amides, and magnesium alkoxides

• Mateo Berton,
• Kevin Sheehan,
• Andrea Adamo and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2020, 16, 1343–1356, doi:10.3762/bjoc.16.115

• Abstract Magnesium organometallic reagents occupy a central position in organic synthesis. The freshness of these compounds is the key for achieving a high conversion and reproducible results. Common methods for the synthesis of Grignard reagents from metallic magnesium present safety issues and exhibit a

• batch-to-batch variability. Tubular reactors of solid reagents combined with solution-phase reagents enable the continuous-flow preparation of organomagnesium reagents. The use of stratified packed-bed columns of magnesium metal and lithium chloride for the synthesis of highly concentrated turbo

• Grignards is reported. A low-cost pod-style synthesizer prototype, which incorporates single-use prepacked perfluorinated cartridges and bags of reagents for the automated on-demand lab-scale synthesis of carbon, nitrogen, and oxygen turbo magnesium bases is presented. This concept will provide access to

Architecture and synthesis of P,N-heterocyclic phosphine ligands

• Wisdom A. Munzeiwa,
• Bernard Omondi and
• Vincent O. Nyamori

Beilstein J. Org. Chem. 2020, 16, 362–383, doi:10.3762/bjoc.16.35

• reagents has been reported by Kluver et al. [54], by which the product was isolated in excellent yield (71%). It was noted that the magnesium ions increase the water partition coefficient of these compounds since they coordinate stronger to the nitrogen atoms as compared to lithium ions. In this case

• magnesium-containing triazoles 66 which, upon quenching with ammonium chloride, afforded the triazoles 67. Lithiation followed by coupling with the appropriate chlorophosphines resulted in the desired 1,5-disubstitued triazolylphosphine ligands 68. The procedure could be performed in one pot by directly

• deprotection then furnished 83b in reasonable yields between 68 and 87%. Bis(diphenylphosphine)-substituted imidazoles were also synthesized by Karthik et al. [87] starting from the diiodoimidazole derivative 84. The lithium chloride mediated magnesium/iodine exchange reaction of 84 followed by the addition of

Formal preparation of regioregular and alternating thiophene–thiophene copolymers bearing different substituents

• Atsunori Mori,
• Keisuke Fujita,
• Chihiro Kubota,
• Toyoko Suzuki,
• Kentaro Okano,
• Takuya Matsumoto,
• Takashi Nishino and
• Masaki Horie

Beilstein J. Org. Chem. 2020, 16, 317–324, doi:10.3762/bjoc.16.31

• to afford the regioregular polythiophene in which 2,5-dihalo-3-substituted thiophene 1 is employed as a monomer precursor, converting to the corresponding organometallic monomer by a halogen−magnesium exchange reaction with a Grignard reagent. The employment of 1 leading to polythiophene has been

• shown to proceed in a dehalogenative manner [3]. We have recently shown that the generation of the organometallic monomer species can alternatively also be achieved by deprotonation, using 2-halo-3-substituted thiophene 2 or 3 with a bulky magnesium amide Knochel–Hauser base (TMPMgCl⋅LiCl) [7], followed

Understanding the role of active site residues in CotB2 catalysis using a cluster model

• Keren Raz,
• Ronja Driller,
• Thomas Brück,
• Bernhard Loll and
• Dan T. Major

Beilstein J. Org. Chem. 2020, 16, 50–59, doi:10.3762/bjoc.16.7

• reaction. The coordinates of the amino acids and the substrate GGPP were taken from the corresponding X-ray structure, with a resolution of 1.8 Å [42]. In this approach, geometry optimizations with the “Modredundant” keyword were performed, and the active site residues, diphosphate moiety, and magnesium

Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles

• Hoang Huy Do,
• Saif Ullah,
• Alexander Villinger,
• Joanna Lecka,
• Jean Sévigny,
• Peter Ehlers,
• Jamshed Iqbal and
• Peter Langer

Beilstein J. Org. Chem. 2019, 15, 2830–2839, doi:10.3762/bjoc.15.276

• considering an already reported colorimetric method with minor modifications [38][39][40][41]. The reaction buffer was comprised of 50 mM Tris-hydrochloric acid, 5 mM magnesium chloride (MgCl2) and 0.1 mM zinc chloride (ZnCl2) with final pH 9.5. For initial screening of compounds, first enzyme and substrate

Acid-catalyzed rearrangements in arenes: interconversions in the quaterphenyl series

• Sarah L. Skraba-Joiner,
• Carter J. Holt and
• Richard P. Johnson

Beilstein J. Org. Chem. 2019, 15, 2655–2663, doi:10.3762/bjoc.15.258

• , 3H). Synthesis of o,o’-quaterphenyl (17) [36]: A solution of 2-bromobiphenyl (0.15 g, 0.65 mmol), magnesium turnings (0.02 g, 0.69 mmol), and THF (2 mL) was stirred at ambient temperature overnight under a nitrogen atmosphere. Additional THF (4 mL) was added and the reaction mixture was cooled to −78

A new approach to silicon rhodamines by Suzuki–Miyaura coupling – scope and limitations

• Thines Kanagasundaram,
• Antje Timmermann,
• Carsten S. Kramer and
• Klaus Kopka

Beilstein J. Org. Chem. 2019, 15, 2569–2576, doi:10.3762/bjoc.15.250

• added the double Grignard reagent 4 to methyl esters 5 [26]. A similar approach was established by Lavis, herein electrophiles (anhydrides or esters) were added to lithium or magnesium organyls 4 [27]. Johnsson and co-workers could establish dye formation by addition of aryllithium 7 to the silicon

Chiral terpene auxiliaries V: Synthesis of new chiral γ-hydroxyphosphine oxides derived from α-pinene

• Anna Kmieciak and
• Marek P. Krzemiński

Beilstein J. Org. Chem. 2019, 15, 2493–2499, doi:10.3762/bjoc.15.242

• added dropwise. After 3 h, the mixture was filtered, 10% sodium metabisulphite (15 mL) was added to the filtrate, and the mixture was stirred for 10 min. The layers were separated, the organic layer was washed with 1 M NaOH (2 × 15 mL), brine (10 mL), and dried over anhydrous magnesium sulfate. The

• solution. The layers were separated and the aqueous layer was extracted with diethyl ether (2 × 20 mL). The combined organic layers were washed with brine (15 mL), dried with anhydrous magnesium sulfate, filtered and the solvents were removed using a rotary evaporator. The product was purified by column

• brine (5 mL). After drying the solution with anhydrous magnesium sulfate and filtration, the solvent was evaporated and the product was purified by flash chromatography on silica gel (hexane/ethyl acetate 80:20). Phosphine 23 (0.131 g, 62%) was obtained as a colorless oil. 1H NMR (700 MHz, CDCl3) δ 0.93

Functionalization of 4-bromobenzo[c][2,7]naphthyridine via regioselective direct ring metalation. A novel approach to analogues of pyridoacridine alkaloids

• Benedikt C. Melzer,
• Alois Plodek and
• Franz Bracher

Beilstein J. Org. Chem. 2019, 15, 2304–2310, doi:10.3762/bjoc.15.222

• bromo substituent of the appropriate substrates 20a or 20b should converted into the respective organomagnesium product by bromine–magnesium exchange. In an expected subsequent Parham-type ring-closing reaction [33] the nucleophilic carbon at position 4 should trap the ester (or nitrile) group to lead

• . Reaction of 20a with 2.2 equiv iPrMgCl∙LiCl, which is a very mild reagent for bromine–magnesium exchange reactions in the presence of labile functional groups like esters [35], at 0 °C led, after aqueous work-up, to the formation of the expected pyridoacridone 22 in 28% yield (Scheme 5). Although starting

• material could not be recovered, another product 23, which is most likely the debrominated, not cyclized analogue of 20a, was observed in traces. The outcome of this experiment shows that the bromine–magnesium exchange reaction was most likely completed, but the intramolecular trapping of the ester group

1,2,3,4-Tetrahydro-1,4,5,8-tetraazaanthracene revisited: properties and structural evidence of aromaticity loss

• Arnault Heynderickx,
• Sébastien Nénon,
• Olivier Siri,
• Vladimir Lokshin and
• Vladimir Khodorkovsky

Beilstein J. Org. Chem. 2019, 15, 2059–2068, doi:10.3762/bjoc.15.203

• ). The extracts were dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel using CH2Cl2/AcOEt/MeOH (8:2:1) as eluent, to give the titled product (696 mg, 96%) as colorless solid. Mp: 232 °C (244 °C [8]); 1H NMR (CDCl3) δ 2.37 (s, 6H), 4.05

• , the solvents were evaporated in vacuo and the residue was dissolved in dichloromethane (50 mL). The organic layer was washed with an aqueous sodium hydroxide (1 M, 2 × 5 mL), then with water (10 mL), dried over magnesium sulfate, evaporated. The crude product was purified by column chromatography on

• hydroxide (1 M, 2 × 5 mL), then with water (10 mL), dried over magnesium sulfate, and evaporated. The crude product was purified by column chromatography on silica gel using cyclohexane/AcOEt (3:7) to furnish the titled product in 48% yield (348 mg) as a yellow solid. 1H NMR (CDCl3) δ 1.38 (s, 9H), 3.67 (t