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

Recent advances in transition-metal-catalyzed intermolecular carbomagnesiation and carbozincation

• Kei Murakami and
• Hideki Yorimitsu

Beilstein J. Org. Chem. 2013, 9, 278–302, doi:10.3762/bjoc.9.34

• allylmagnesiation of alkynyl sulfone. Copper-catalyzed four-component reaction of alkynyl sulfoxide with alkylzinc reagent, diiodomethane, and benzaldehyde. Rhodium-catalyzed reaction of aryl alkynyl ketones with arylzinc reagents. Allylmagnesiation of propargyl alcohol, which provides the anti-addition product

Interaction of cyclodextrins with pyrene-modified polyacrylamide in a mixed solvent of water and dimethyl sulfoxide as studied by steady-state fluorescence

• Akihito Hashidzume,
• Yongtai Zheng and
• Akira Harada

Beilstein J. Org. Chem. 2012, 8, 1312–1317, doi:10.3762/bjoc.8.150

• Gobancho, Chiyoda-ku, Tokyo 102-0076, Japan 10.3762/bjoc.8.150 Abstract The interaction of β- and γ-cyclodextrins (β-CD and γ-CD, respectively) with polyacrylamide modified with pyrenyl (Py) residues (pAAmPy) was investigated in a mixed solvent of water and dimethyl sulfoxide (DMSO) by steady-state

• ][36]. Recently, we have demonstrated this selectivity switching on macroscopic molecular recognition for polyacrylamide-based gels carrying pyrenyl (Py) and CD residues, by changing the composition of a mixed solvent of water and dimethyl sulfoxide (DMSO) [37]. In the present study, the interaction of

Cyclodextrin nanosponge-sensitized enantiodifferentiating photoisomerization of cyclooctene and 1,3-cyclooctadiene

• Wenting Liang,
• Cheng Yang,
• Masaki Nishijima,
• Gaku Fukuhara,
• Tadashi Mori,
• Andrea Mele,
• Franca Castiglione,
• Fabrizio Caldera,
• Francesco Trotta and
• Yoshihisa Inoue

Beilstein J. Org. Chem. 2012, 8, 1305–1311, doi:10.3762/bjoc.8.149

• very low temperatures (below −100 °C). Results and Discussion CDNSs 3, 4 and 5 were prepared in almost quantitative yields by reacting pyromellitic dianhydride (PDA) with β-CD or γ-CD in the presence of triethylamine in dimethyl sulfoxide at room temperature (Scheme 1) and purified by extensive Soxhlet

Control over molecular motion using the cis–trans photoisomerization of the azo group

• Estíbaliz Merino and
• María Ribagorda

Beilstein J. Org. Chem. 2012, 8, 1071–1090, doi:10.3762/bjoc.8.119

• arylhydrazines 18 [134]. In both cases, the sulfoxide group preferentially adopts a rigid S-cis conformation [135], situating the sulfinylic oxygen in 1,3-parallel arrangement with the neighbouring hydrogen (blue arrow, Scheme 1). This arrangement is essential to force a specific final conformation of the

• standard techniques (UV–vis, circular dichroism, chiral HPLC and NMR) has established that the chiral optical response differs greatly depending on the position of the sulfoxide group (C-2 or C-3). Cis isomers in both p-tolylsulfinyl azocompounds show an opposite arrangement of substituents around the N=N

• group, with an S-shaped structure for cis-20 or a U-shaped structure for cis-21. The conformational rigidity of the chiral sulfinyl group is the key to controlling the directionality of the molecular motion of photoisomerization. Thus, choosing the position of the sulfoxide group in the azobenzene

Intramolecular bridges formed by photoswitchable click amino acids

• Christian Hoppmann,
• Ronald Kühne and
• Michael Beyermann

Beilstein J. Org. Chem. 2012, 8, 884–889, doi:10.3762/bjoc.8.100

• the yield of the intramolecular thiol click reaction increased (Figure 2, data shown for peptide 1). At the highest GSH concentration tested (10 mM), only the intermolecular click product 5 ([M + 2H]2+ = 960.90) was detected as the corresponding sulfoxide of the thioether formed in the crosslinked

Synthesis and characterization of a novel carboxyl group containing (co)polyimide with sulfur in the polymer backbone

• Miroslav Mrsevic,
• David Düsselberg and
• Claudia Staudt

Beilstein J. Org. Chem. 2012, 8, 776–786, doi:10.3762/bjoc.8.88

• solubility in amidic solvents, such as dimethylacetamide (DMAC), dimethylformamide (DMF), and N-methyl-2-pyrrolidone (NMP), as well as in other non-amidic solvents, such as tetrahydrofuran (THF), dimethyl sulfoxide (DMSO) and acetone. No differences in solubility either between the different (co)polyimides

Alkoxide-induced ring opening of bicyclic 2-vinylcyclobutanones: A convenient synthesis of 2-vinyl-substituted 3-cycloalkene-1-carboxylic acid esters

• Xiufang Ji,
• Zhiming Li,
• Quanrui Wang and
• Andreas Goeke

Beilstein J. Org. Chem. 2012, 8, 650–657, doi:10.3762/bjoc.8.72

• ][7][8]. In this context, α,α-dihalosubstituents, thioketal, sulfoxide, ester or aryl substituents have been reported to facilitate the ring cleavage [6][7][8]. We recently reported a novel metathetic cycloreversion of 7-vinyl and aryl bicyclo[3.2.0]hept-2-en-6-ones giving rise to linear polyene

Synthesis of szentiamide, a depsipeptide from entomopathogenic Xenorhabdus szentirmaii with activity against Plasmodium falciparum

• Friederike I. Nollmann,
• Andrea Dowling,
• Marcel Kaiser,
• Klaus Deckmann,
• Sabine Grösch,
• Richard ffrench-Constant and
• Helge B. Bode

Beilstein J. Org. Chem. 2012, 8, 528–533, doi:10.3762/bjoc.8.60

• cells were treated with increasing concentrations of the compound (10, 50 and 100 µM) or dimethyl sulfoxide. After 24 h, 10 µL of WST-1 reagent was added to each well and the cells were incubated for a further 90–150 min. The formation of the formazan was measured at 450 nm against a reference