Influence of cyclodextrin on the UCST- and LCST-behavior of poly(2-methacrylamido-caprolactam)-co-(N,N-dimethylacrylamide)

• Alexander Burkhart and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 1951–1958, doi:10.3762/bjoc.10.203

• Avance DRX 300 by using dimethyl sulfoxide-d6 or chloroform-d as solvents. The chemical shifts (δ) are given in parts per million (ppm) using the solvent peak as an internal standard. 2D NMR-spectroscopy was performed using a Bruker Avance III DRX 300 at 300 MHz in D2O as a solvent. The samples were

• molar ratios (according to Table 1) with N,N-dimethylacrylamide (5) in dimethyl sulfoxide (total monomer concentration 1.8 mol L−1). 1 mol % of 2,2’-azobis(2-methylpropionitrile) with respect to monomers 4 and 5 were added to the solution under nitrogen. Under stirring, the solution was heated to 110 °C

Macrocyclic bis(ureas) as ligands for anion complexation

• Claudia Kretschmer,
• Gertrud Dittmann and
• Johannes Beck

Beilstein J. Org. Chem. 2014, 10, 1834–1839, doi:10.3762/bjoc.10.193

• ring with two ethynylene groups as linkers and 2 the larger ring with two butadiynylene groups. On thermal treatment to 130 °C molecule 1 splits up into two dihydroindoloquinolinone (3) molecules. Both compounds 1 and 2 form adducts with polar molecules such as dimethyl sulfoxide (DMSO) and

• isocyanates lead to indoloquinolinones. The crystal structure of the N-methylated congener of 3 has been determined [15]. Thermal treatment of 2 does not lead to fragmentation or sublimation of volatile material as observed for 1. Macrocycle 2 is soluble in dimethylformamide (DMF) or dimethyl sulfoxide (DMSO

Multivalent scaffolds induce galectin-3 aggregation into nanoparticles

• Candace K. Goodman,
• Mark L. Wolfenden,
• Pratima Nangia-Makker,
• Anna K. Michel,
• Avraham Raz and
• Mary J. Cloninger

Beilstein J. Org. Chem. 2014, 10, 1570–1577, doi:10.3762/bjoc.10.162

• reported in ppm from tetramethylsilane with the residual protic solvent resonance as the internal standard (chloroform: δ 7.25 ppm; dimethyl sulfoxide: δ 2.50 ppm). Data are reported as follows: chemical shift, multiplicity (s = singlet, bs = broad singlet, d = doublet, t = triplet, q = quartet, p = pentet

Bis(β-lactosyl)-[60]fullerene as novel class of glycolipids useful for the detection and the decontamination of biological toxins of the Ricinus communis family

• Hirofumi Dohi,
• Takeru Kanazawa,
• Akihiro Saito,
• Keita Sato,
• Hirotaka Uzawa,
• Yasuo Seto and
• Yoshihiro Nishida

Beilstein J. Org. Chem. 2014, 10, 1504–1512, doi:10.3762/bjoc.10.155

• aggregates were diluted with dimethyl sulfoxide (DMSO) and dialyzed against distilled water for 2 days to give a colloidal suspension of bis-Lac-C60 with a deep brown color. The derived suspension was stable for at least 6 months when stored at 4 °C in the dark. Dynamic light scattering (DLS) analysis

• dimethyl sulfoxide (2 mL), and the solution was poured into a dialysis tube (Cellulose Dialyzer Tubing VT351, molecular weight cut-off: 3500, Nacalai Tesque, Inc., Japan) suffused with distilled water (20 mL). After 2 days of dialysis, the solution was subjected to ultrafiltration at 3,000g for 15 min by

Biantennary oligoglycines and glyco-oligoglycines self-associating in aqueous medium

• Svetlana V. Tsygankova,
• Alexander A. Chinarev,
• Alexander B. Tuzikov,
• Nikolai Severin,
• Alexey A. Kalachev,
• Juergen P. Rabe,
• Alexandra S. Gambaryan and
• Nicolai V. Bovin

Beilstein J. Org. Chem. 2014, 10, 1372–1382, doi:10.3762/bjoc.10.140

• ). Et3N (8 mmol) followed by BocGlyONSu or BocGly2ONSu (3 mmol) were added to a solution of diamine (1 mmol) in dimethyl sulfoxide (DMSO; 5 mL). The reaction mixture was stirred until the disappearance of the starting diamine (1–24 h, TLC control) and the solvent was removed under vacuum. The dry residue

Direct C–H trifluoromethylation of di- and trisubstituted alkenes by photoredox catalysis

• Ren Tomita,
• Yusuke Yasu,
• Takashi Koike and
• Munetaka Akita

Beilstein J. Org. Chem. 2014, 10, 1099–1106, doi:10.3762/bjoc.10.108

• dibenzothiophene to sulfoxide, which was more easily separated from the products. After the solution was stirred at room temperature for 2 h, an aqueous solution of Na2S2O3·5H2O was added to the solution, which was extracted with CH2Cl2. The organic layer was washed with H2O, dried (Na2SO4), and filtered. The

End-group-functionalized poly(N,N-diethylacrylamide) via free-radical chain transfer polymerization: Influence of sulfur oxidation and cyclodextrin on self-organization and cloud points in water

• Sebastian Reinelt,
• Daniel Steinke and
• Helmut Ritter

Beilstein J. Org. Chem. 2014, 10, 680–691, doi:10.3762/bjoc.10.61

• wave length of 1024 cm−1 corresponding to the S=O stretching vibration of the sulfoxide [11] and no shift of the C=O vibration at 1625 cm–1. Additionally, the 1H NMR spectrum clearly indicated an upfield shift of the OCH2-group supporting also a successful oxidation. Thus the analytical data reveals no

• influence of their oxidation to sulfoxides on the cloud point was investigated. The more hydrophilic polar sulfoxide group in comparison to the thioether group should lead to an increase of solubility in water. Thus higher cloud point values for all polymers were found (see Table 2). The cloud point shifts

An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y

• Suresh Babu Meruva,
• Akula Raghunadh,
• Raghavendra Rao Kamaraju,
• U. K. Syam Kumar and
• P. K. Dubey

Beilstein J. Org. Chem. 2014, 10, 471–480, doi:10.3762/bjoc.10.45

• -ketoamides (9a–9j) A mixture of 2,2-dibromo-1-phenylethanone (11a, 6.0 g, 21.6 mmol) and sodium iodide (6.48 g, 43.2 mmol) in dimethyl sulfoxide (30.0 mL) at 25–45 °C was stirred for 40–50 minutes. Triethylamine (6.55 g, 64.8 mmol) and tryptamine (10, 3.45 g, 21.6 mmol) were then added to the mixture under a

A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-(arylamino)allyl]chromen-4-ones

• Pitchaimani Prasanna,
• Pethaiah Gunasekaran,
• Subbu Perumal and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2014, 10, 459–465, doi:10.3762/bjoc.10.43

• ), (E)-3-(dimethylamino)-1-(3-nitrophenyl)prop-2-en-1-one (1 mmol) and 4-methoxyaniline (1 mmol). This three-component reaction was initially examined in solvents such as acetonitrile, dioxane, dimethyl sulfoxide, toluene and ethanol under heating. However, the only isolable product was compound 4d

• , acetonitrile, dimethyl sulfoxide, ethanol, ethylene glycol) in the presence of one equivalent of HCl, but all these attempts failed, while the same conditions were successful in DMF. These results can be explained by assuming that the initial aldol-type reaction between 1 and 4 to give 6 is reversible and is

Carbenoid-mediated nucleophilic “hydrolysis” of 2-(dichloromethylidene)-1,1,3,3-tetramethylindane with DMSO participation, affording access to one-sidedly overcrowded ketone and bromoalkene descendants^§

• Rudolf Knorr,
• Thomas Menke,
• Johannes Freudenreich and
• Claudio Pires

Beilstein J. Org. Chem. 2014, 10, 307–315, doi:10.3762/bjoc.10.28

• (dimethylamino)phosphinoxide, five hours at 150 °C], and in acetonitrile (23 hours, 70 °C). Reisolation of pure 6 from hot formic acid (44 hours, 90 °C) or from dimethyl sulfoxide solution (DMSO, five hours at 156 °C without a base) showed that C–Cl bond heterolysis (vinylic SN1 reaction) did not occur in these

• (ca. 0.001 M [21]) of KOH in DMSO. Granting preference to the chlorine transfer from 6 to 11, the byproduct 13 of 12 would hardly be traceable: even if 13 reacted with 11, for example, the resultant water-soluble [28] bis(sulfoxide) 16 might get lost in the usual procedure of aqueous work-up. As an

• (2.80 g, 11.0 mmol), dimethyl sulfoxide (45 mL), and a magnetic stirring bar were placed in a round-bottomed flask carrying either a wide-bore connection to a cooled trap or a T-shaped glass-tube with a bubbler and gas inlet. This suspension was stirred at 60 °C until 6 was completely dissolved. Freshly

Synthesis of five- and six-membered cyclic organic peroxides: Key transformations into peroxide ring-retaining products

• Alexander O. Terent'ev,
• Dmitry A. Borisov,
• Vera A. Vil’ and
• Valery M. Dembitsky

Beilstein J. Org. Chem. 2014, 10, 34–114, doi:10.3762/bjoc.10.6

Charge-transfer interaction mediated organogels from 18β-glycyrrhetinic acid appended pyrene

• Jun Hu,
• Jindan Wu,
• Qian Wang and
• Yong Ju

Beilstein J. Org. Chem. 2013, 9, 2877–2885, doi:10.3762/bjoc.9.324

• 30 min to see whether there was any flow of solvent. It showed that dark red CT gels (Figure 1c) were obtained in dimethyl sulfoxide (DMSO)/water and N,N-dimethylformamide (DMF)/water mixed solvents (Table 1, entries 3, 4 and 9, 10), but not in respective individual solvent system (DMSO, water or DMF

N,N'-(Hexane-1,6-diyl)bis(4-methyl-N-(oxiran-2-ylmethyl)benzenesulfonamide): Synthesis via cyclodextrin mediated N-alkylation in aqueous solution and further Prilezhaev epoxidation

• Julian Fischer,
• Simon Millan and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2834–2840, doi:10.3762/bjoc.9.318

• (99+%) were purchased from Acros Organics, bisphenol A diglycidyl ether and deuterium oxide (99.9%) were provided from Sigma Aldrich, chloroform-d (99.80%) was obtained from Euriso-Top and dimethyl sulfoxide-d6 (99.9%) was purchased from Deutero. 1H NMR, 13C NMR and 2D ROESY spectra were recorded on a

• Bruker Avance DRX 300 and a Bruker Avance III – 600 by using deuterium oxide, dimethyl sulfoxide-d6 or chloroform-d as solvents. The chemical shifts (δ) are given in parts per million (ppm) using the solvent peak as an internal standard. FTIR spectra were recorded on a Nicolet 6700 FTIR spectrometer

3-Pyridinols and 5-pyrimidinols: Tailor-made for use in synergistic radical-trapping co-antioxidant systems

• Luca Valgimigli,
• Daniele Bartolomei,
• Riccardo Amorati,
• Evan Haidasz,
• Jason J. Hanthorn,
• Susheel J. Nara,
• Johan Brinkhorst and
• Derek A. Pratt

Beilstein J. Org. Chem. 2013, 9, 2781–2792, doi:10.3762/bjoc.9.313

• solvents of different HBA ability [30]: acetonitrile ( = 0.44), ethyl acetate ( = 0.45), and dimethyl sulfoxide ( = 0.78) using IR spectroscopy [25]. Representative results are shown in Figure 2. Addition of a HBA solvent to solutions of the pyri(mi)dinols in non-H-bonding CCl4 resulted in the progressive

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

• added in three- to ten-fold excess (Scheme 2) [18]. This procedure is tolerant towards most functional groups, even free amines, alcohols and carboxylic acids, and can be carried out in aqueous reaction media with organic co-solvents such as alcohols or dimethyl sulfoxide. As an alternative reducing

• investigations have focused on kinetic measurements. The catalytic activity in the presence of the ligands presented in Table 1 (0.2 mM) was assessed in the test reaction of phenylacetylene (2 mM) with benzyl azide (1 mM) in a solvent mixture of dimethyl sulfoxide and aqueous buffer in the presence of sodium

• consequence, they suggested two copper centres to be required for catalytic turnover. Mechanistic studies for the “ligand-free” CuAAC followed [160]. The reaction of benzyl azide with phenylacetylene in dimethyl sulfoxide/water in the presence of copper(II) sulfate pentahydrate and an excess of sodium

Recent advances in transition metal-catalyzed Csp²-monofluoro-, difluoro-, perfluoromethylation and trifluoromethylthiolation

• Grégory Landelle,
• Armen Panossian,
• Sergiy Pazenok,
• Jean-Pierre Vors and
• Frédéric R. Leroux

Beilstein J. Org. Chem. 2013, 9, 2476–2536, doi:10.3762/bjoc.9.287

An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles

• Marcus Baumann and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2013, 9, 2265–2319, doi:10.3762/bjoc.9.265

• proton pump inhibitors; numerous examples such as omeprazole (1.29, Losec), rabeprazole (1.33, Aciphex), pantoprazole (1.34, Protonix) and lansoprazole (1.35, Prevacid) populate this area [28]. All these API’s contain the characteristic benzimidazole unit bearing a sulfoxide substituent at the 2-position

Gold-catalyzed regioselective oxidation of propargylic carboxylates: a reliable access to α-carboxy-α,β-unsaturated ketones/aldehydes

• Kegong Ji,
• Jonathan Nelson and
• Liming Zhang

Beilstein J. Org. Chem. 2013, 9, 1925–1930, doi:10.3762/bjoc.9.227

• the sulfoxide, 5a-OAc was formed in only 5% yield even at 60 °C after 12 h (Scheme 4); moreover, the major product in the reaction was the expected enone 6 (56% yield, 88% conversion) due to a dominant gold-catalyzed 3,3-rearrangement; c) this alternative could not rationalize the formation of 5a-H

• approach. Gold-catalyzed regioselective oxidation of a sterically biased internal alkyne. Gold-catalyzed oxidation of the propargylic acetate 4a and the mechanistic rationale. A drastically different outcome by using diphenyl sulfoxide as the oxidant. Reaction scope studies for the formation of α

Aerobic radical multifunctionalization of alkenes using tert-butyl nitrite and water

• Daisuke Hirose and
• Tsuyoshi Taniguchi

Beilstein J. Org. Chem. 2013, 9, 1713–1717, doi:10.3762/bjoc.9.196

• radical oxynitration. Results and Discussion Our investigation started with the screening of solvents in the reaction of alkene 1 with t-BuONO (3 equiv) and oxygen in the presence of water (3 equiv). Although dimethyl sulfoxide (DMSO) was the best solvent in the reaction without water to obtain γ-lactol 2

New tridecapeptides of the theonellapeptolide family from the Indonesian sponge Theonella swinhoei

• Annamaria Sinisi,
• Barbara Calcinai,
• Carlo Cerrano,
• Henny A. Dien,
• Angela Zampella,
• Claudio D’Amore,
• Barbara Renga,
• Stefano Fiorucci and
• Orazio Taglialatela-Scafati

Beilstein J. Org. Chem. 2013, 9, 1643–1651, doi:10.3762/bjoc.9.188

• 3.86, with these latter signals showing HMBC correlations both with the methyl carbon at δC 39.2 and an amide carbonyl resonating at δC 166.5. The 1H and 13C NMR chemical shift values of both the methyl and the methylene groups strongly suggested their linkage to a sulfoxide group, and the presence of

Stability of SG1 nitroxide towards unprotected sugar and lithium salts: a preamble to cellulose modification by nitroxide-mediated graft polymerization

• Guillaume Moreira,
• Laurence Charles,
• Mohamed Major,
• Florence Vacandio,
• Yohann Guillaneuf,
• Catherine Lefay and
• Didier Gigmes

Beilstein J. Org. Chem. 2013, 9, 1589–1600, doi:10.3762/bjoc.9.181

• efficient to solubilize polysaccharides, is DMA in the presence of LiCl (generally 5 to 10 wt % versus DMA) [15]. This system has already been reported to successfully solubilize cellulose before grafting modification by ATRP in dimethyl sulfoxide (DMSO) [16], but not in the case of NMP yet. Indeed, to our

Molecular assembly of amino acid interlinked, topologically symmetric, π-complementary donor–acceptor–donor triads

• M. B. Avinash,
• K. V. Sandeepa and
• T. Govindaraju

Beilstein J. Org. Chem. 2013, 9, 1565–1571, doi:10.3762/bjoc.9.178

• then subjected to amide coupling with pyrenemethylamine to obtain the triads (1–3) in good yield. UV–vis absorption spectra of 1 in dimethyl sulfoxide (DMSO) exhibit absorption bands in the region of 270–400 nm due to characteristic π–π* transitions of pyrene and NDI (Figure 2a). With the successive

A³-Coupling catalyzed by robust Au nanoparticles covalently bonded to HS-functionalized cellulose nanocrystalline films

• Jian-Lin Huang,
• Derek G. Gray and
• Chao-Jun Li

Beilstein J. Org. Chem. 2013, 9, 1388–1396, doi:10.3762/bjoc.9.155

• , tetrahydrofuran (THF), ethyl acetate (EA), dimethyl sulfoxide (DMSO), and N,N-dimethylformamide (DMF) afforded the products in moderate or low conversions (Table 1, entries 16–22). The optimized reaction conditions include 1.0 equiv of aldehyde, 1.2 equiv of amine, 1.5 equiv of alkyne, and 4.4 mol % of Au

Appel-reagent-mediated transformation of glycosyl hemiacetal derivatives into thioglycosides and glycosyl thiols

• Tamashree Ghosh,
• Abhishek Santra and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2013, 9, 974–982, doi:10.3762/bjoc.9.112

• ][2][3][4][5]. Due to their thermal and chemical stability, they have been used as stable intermediates for functional-group transformations as well as stereoselective glycosylations. Thioglycosides can be transformed into various other glycosyl donors [6][7][8][9][10] (e.g., sulfoxide, sulfone

Superstructures of fluorescent cyclodextrin via click-reaction

• Arkadius Maciollek,
• Helmut Ritter and
• Rainer Beckert

Beilstein J. Org. Chem. 2013, 9, 827–831, doi:10.3762/bjoc.9.94

• without further purification. β-CD was obtained from Wacker Chemie GmbH, Burghausen, Germany and was used after drying overnight with a vacuum oil pump over P4O10. N,N-Dimethylformamide (DMF) was purchased from Fluka, Germany. Dimethyl sulfoxide-d6 (99.9 atom % D) and deuterium oxide, D2O, were obtained