Microwave-assisted Cu(I)-catalyzed, three-component synthesis of 2-(4-((1-phenyl-1H-1,2,3-triazol-4-yl)methoxy)phenyl)-1H-benzo[d]imidazoles

• Yogesh Kumar,
• Vijay Bahadur,
• Anil K. Singh,
• Virinder S. Parmar,
• Erik V. Van der Eycken and
• Brajendra K. Singh

Beilstein J. Org. Chem. 2014, 10, 1413–1420, doi:10.3762/bjoc.10.145

• . We explored the reaction between phenylazide (1a), 4-(prop-2-yn-1-yloxy)benzaldehyde (2a) and 1,2-diaminobenzene (3a). It was found that when the reactions were carried out in polar solvents, such as acetonitrile, N,N-dimethylformamide (DMF), dimethylsulfoxide (DMSO) or 1,4-dioxane, no product

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

• ). First the chain-transfer constant of 6a and 6b for the polymerization of DEAAm in N,N-dimethylformamide (DMF) at 70 °C was calculated from experimental results by using the Mayo method [39]. Chain-transfer constants of CTr,6a = 0.84 and CTr,6b = 0.87 were found (see Supporting Information File 1, Figure

Continuous-flow Heck synthesis of 4-methoxybiphenyl and methyl 4-methoxycinnamate in supercritical carbon dioxide expanded solvent solutions

• Phei Li Lau,
• Ray W. K. Allen and
• Peter Styring

Beilstein J. Org. Chem. 2013, 9, 2886–2897, doi:10.3762/bjoc.9.325

• are carried out in polar aprotic solvents, such as N,N-dimethylformamide (DMF), 1-methyl-2-pyrrolidone (NMP) and N,N-dimethylacetamide (DMA), though other organic solvents, such as toluene, hexane, methanol and ethanol have been utilised [6]. In addition, the reactions have been carried out in

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

Garner’s aldehyde as a versatile intermediate in the synthesis of enantiopure natural products

• Mikko Passiniemi and
• Ari M.P. Koskinen

Beilstein J. Org. Chem. 2013, 9, 2641–2659, doi:10.3762/bjoc.9.300

• stability of all intermediates. In his original paper, Garner first protected the amino group with Boc anhydride in dioxane, then esterified the carboxylic acid with iodomethane under basic conditions in dimethylformamide (DMF) and finally formed the dimethyloxazolidine ring of 4 with catalytic p

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

• [21], it worked inefficiently in the presence of water, and triple functionalized product 3 was obtained in low yield along with a large amount of oxynitration product 4 (Table 1, entry 1). The use of other polar solvents such as N,N-dimethylformamide (DMF) and tetrahydrofuran (THF) also did not give

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

• solubilize cellulose in N,N-dimethylformamide (DMF) or N,N-dimethylacetamide (DMA) with 5 to 10 wt % of lithium salts (LiCl or LiBr), and carry out grafted polymerization in this medium. The stability of nitroxides such as SG1 has not been studied under these conditions yet, even though these parameters are

• , 99+%), sodium perchlorate (NaClO4, Aldrich, ACS reagent ≥98%), tetrabutylammonium hexafluorophosphate (TBAPF6, Fluka, 98+%), TEMPO (Aldrich, 98%), styrene (Aldrich, 99+%), N,N-dimethylformamide (DMF, SDS, Analytical grade), N,N-dimethylacetamide (DMA, Aldrich, 99.5+%), sodium chloride (NaCl, Carlo

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

Camera-enabled techniques for organic synthesis

• Steven V. Ley,
• Richard J. Ingham,
• Matthew O’Brien and
• Duncan L. Browne

Beilstein J. Org. Chem. 2013, 9, 1051–1072, doi:10.3762/bjoc.9.118

• inline evaporation apparatus was developed to perform a solvent switch from dichloromethane (DCM) to dimethylformamide (DMF). The reactor output was dripped into a heated vial containing DMF where a flow of nitrogen gas removed the DCM solvent (Figure 23). A pump removed the concentrated solution through

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

Polar reactions of acyclic conjugated bisallenes

• Reiner Stamm and
• Henning Hopf

Beilstein J. Org. Chem. 2013, 9, 36–48, doi:10.3762/bjoc.9.5

• ) accounts for our experimental observations. Regardless of the exact structures of the silylation products 21, we did not observe any selectivity in this transformation. Quenching of 4 with N,N-dimethylformamide (DMF) and acetone Metalated allenes are known to be converted into allenic aldehydes on DMF

Influence of cyclodextrin on the solubility and the polymerization of (meth)acrylated Triton^® X-100

• Melanie Kemnitz and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 2176–2183, doi:10.3762/bjoc.8.245

• orientation of the CD ring could be drawn. An interaction between CD and the (meth)acrylic group could not be detected. In the course of DLS experiments with dimethylformamide (DMF) as solvent a hydrodynamic diameter of 1.4 nm for pure RAMEB-CD and 1.2 nm for 3 was found. For each complexed RAMEB-CD the

Cyclodextrin-induced host–guest effects of classically prepared poly(NIPAM) bearing azo-dye end groups

• Gero Maatz,
• Arkadius Maciollek and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 1929–1935, doi:10.3762/bjoc.8.224

• purification. RAMEB-CD and β-CD were obtained from Wacker Chemie GmbH, Burghausen, Germany and were used after being dried overnight with a vacuum oil pump over P4O10. N,N-Dimethylformamide (DMF) was purchased from Fluka, Germany. Dimethylsulfoxide-d6 (99.9 atom % D) and deuterium oxide, D2O were obtained from

Dimerization of a cell-penetrating peptide leads to enhanced cellular uptake and drug delivery

• Jan Hoyer,
• Ulrich Schatzschneider,
• Michaela Schulz-Siegmund and
• Ines Neundorf

Beilstein J. Org. Chem. 2012, 8, 1788–1797, doi:10.3762/bjoc.8.204

• acid, trypan blue, 5(6)-carboxyfluorescein (CF) and 2,2,2-trifluoroethanol were purchased from Fluka (Taufkirchen, Germany). Chlorambucil (Cbl) and the resazurin-based in vitro toxicology assay kit were purchased from Sigma-Aldrich (Taufkirchen, Germany). N,N-Dimethylformamide (DMF), dichloromethane

Polysiloxane ionic liquids as good solvents for β-cyclodextrin-polydimethylsiloxane polyrotaxane structures

• Narcisa Marangoci,
• Rodinel Ardeleanu,
• Laura Ursu,
• Constanta Ibanescu,
• Maricel Danu,
• Mariana Pinteala and
• Bogdan C. Simionescu

Beilstein J. Org. Chem. 2012, 8, 1610–1618, doi:10.3762/bjoc.8.184

• of β-CD-polydimethylsiloxane polyrotaxane (PRot) was carried out according to a method previously described [17][22] and the compound was obtained as a white powder (approximately 55% yield). PRot was prepared by mixing β-CD in dimethylformamide (DMF, saturated solution) with α,ω-bis(3

Regioselective synthesis of 7,8-dihydroimidazo[5,1-c][1,2,4]triazine-3,6(2H,4H)-dione derivatives: A new drug-like heterocyclic scaffold

• Nikolay T. Tzvetkov,
• Harald Euler and
• Christa E. Müller

Beilstein J. Org. Chem. 2012, 8, 1584–1593, doi:10.3762/bjoc.8.181

• alkylation reagent and potassium carbonate as a base in dry dimethylformamide (DMF) were used. The best yield (92%) was achieved with ethyl 2-bromopropionate and benzyl bromide as alkylating reagents. Although this procedure led to the direct formation of the desired N3-substituted products, the

• -position of 5,5-dimethylhydantoin (6). The subsequent N1-alkylation of 2,5-dioxoimidazolidines 7–10 to the corresponding N,N-disubstituted hydantoins 12–18 was performed with 1.0–1.2 equiv of the appropriate alkylating reagent by using sodium hydride as a base in dry dimethylformamide (DMF) (Table 2

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

• -Dimethylformamide (DMF) and dichloromethane (DCM) were purified by utilizing a glass contour solvent dispensing system. Water was purified by a Millipore Milli-Q system. β-CD and γ-CD were purchased from Junsei Chemical Co. Ltd. and recrystallized twice from water before use. N-1-Pyrenylmethylacrylamide (APy) was

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

Investigation of the network of preferred interactions in an artificial coiled-coil association using the peptide array technique

• Raheleh Rezaei Araghi,
• Carsten C. Mahrenholz,
• Rudolf Volkmer and
• Beate Koksch

Beilstein J. Org. Chem. 2012, 8, 640–649, doi:10.3762/bjoc.8.71

• . In the second coupling step, the anchor position Fmoc-β-alanine-OPfp in dimethylsulfoxide (DMSO) was used. Residual amino functions between the spots were capped by acetylation. The Fmoc group was cleaved by using 20% piperidine in dimethylformamide (DMF). The cellulose-bound peptide arrays were

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

• hexafluorophosphate (HBTU) in dimethylformamide (DMF) and N,N-diisopropylethylamine (DIEA) in N-methylpyrrolidone (NMP), assisted by microwave irradiation. After the final Fmoc-deprotection with 20% piperidine in DMF, the N-terminus was formylated with para-nitrophenyl formate (pNPF) in the presence of N

• /Carbolution Chemicals; c = 0.2 mol/L) was activated in situ with 5 equiv O-benzotriazole-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HBTU; Iris Biotech) in dimethylformamide (DMF; Acros Organics, Belgium; c = 0.5 mol/L) in the presence of 10 equiv N,N-diisopropylethylamine (DIEA; Novabiochem, Darmstadt

Synthesis of mesomeric betaine compounds with imidazolium-enolate structure

• Nina Gonsior,
• Fabian Mohr and
• Helmut Ritter

Beilstein J. Org. Chem. 2012, 8, 390–397, doi:10.3762/bjoc.8.42

• column set up with one Viscotek TSK guard column HHR-H 6.0 mm (ID)_4 cm (L) and two Viscotek TSK GMHHR-M 7.8 mm (ID)_30 cm (L) columns at 60 °C. N,N-Dimethylformamide (DMF, 0.1 M LiCl) was used as eluent at a flow rate of 1 mL min−1. A Viscotek VE 3500 RI detector and a Viscotek Viscometer model 250 were

Synthesis and characterization of new diiodocoumarin derivatives with promising antimicrobial activities

• Hany M. Mohamed,
• Ashraf H. F. Abd EL-Wahab,
• Ahmed M. EL-Agrody,
• Ahmed H. Bedair,
• Fathy A. Eid,
• Mostafa M. Khafagy and
• Kamal A. Abd-EL-Rehem

Beilstein J. Org. Chem. 2011, 7, 1688–1696, doi:10.3762/bjoc.7.199

• ampicillin (30 µg mL−1) as the standard antibiotic reference for antibacterial activity, and calforan (30 µg mL−1) was used as a reference antifungal activity. The tested compounds were dissolved in N,N-dimethylformamide (DMF) to give a solution of 1 mg mL−1. The inhibition zones (diameter of the hole) were

Studies on Pd/NiFe₂O₄ catalyzed ligand-free Suzuki reaction in aqueous phase: synthesis of biaryls, terphenyls and polyaryls

• Sanjay R. Borhade and
• Suresh B. Waghmode

Beilstein J. Org. Chem. 2011, 7, 310–319, doi:10.3762/bjoc.7.41

• Suzuki coupling reaction (Table 1). These results indicated that the reaction in polar aprotic solvents such as dimethylformamide (DMF), dimethylacetamide (DMA), N-methylpyrrolidin-2-one (NMP) and dimethylsulfoxide (DMSO) showed only 34–50% conversion after 2 h (Table 1, entries 1–4). The reaction in

Chiral recognition of macromolecules with cyclodextrins: pH- and thermosensitive copolymers from N-isopropylacrylamide and N-acryloyl-D/L-phenylalanine and their inclusion complexes with cyclodextrins

• Sabrina Gingter,
• Ella Bezdushna and
• Helmut Ritter

Beilstein J. Org. Chem. 2011, 7, 204–209, doi:10.3762/bjoc.7.27

• chloride (97%) and N-isopropylacrylamide (NIPAAm, 97%) were obtained from Aldrich, Germany, and used as received. Azobisisobutyronitrile (AIBN) (96%) and N,N-dimethylformamide (DMF) were purchased from Fluka, Germany. Dimethylsulfoxide-d6 (99.9 atom % D) and deuterium oxide D2O were obtained from Deutero

• Viscotek TSK GMHHR-M 7.8 mm (ID) × 30 cm (L) columns at 60 °C. N,N-Dimethylformamide (DMF, 0.1 M LiCl) was used as eluent at a flow rate of 1 mL·min−1. A Viscotek VE 3500 RI detector and a Viscotek Viscometer model 250 were used. The system was calibrated with polystyrene standards with a molecular range

Formation of epoxide-amine oligo-adducts as OH-functionalized initiators for the ring-opening polymerization of ε-caprolactone

• Julia Theis and
• Helmut Ritter

Beilstein J. Org. Chem. 2010, 6, 938–944, doi:10.3762/bjoc.6.105

• 1 186 000 Da. Dynamic light scattering (DLS) experiments were implemented on a Malvern HPPS-ET apparatus at a temperature of 25 °C using dimethylformamide (DMF) as solvent. Hellma Suprasil precision cells (110-QS) were used. The particle size distribution was derived from a deconvolution of the