Preparation of Pickering emulsions through interfacial adsorption by soft cyclodextrin nanogels

• Shintaro Kawano,
• Toshiyuki Kida,
• Mitsuru Akashi,
• Hirofumi Sato,
• Motohiro Shizuma and
• Daisuke Ono

Beilstein J. Org. Chem. 2015, 11, 2355–2364, doi:10.3762/bjoc.11.257

• to use. Anhydrous N,N-dimethylformamide (DMF) and 1,4-phenylene diisocyanate (PDI) were purchased from Wako Pure Chemical Industries, Ltd. (Japan). Toluene and n-dodecane were purchased from Kanto Chemical Co., Ltd. (Japan). Fluorescein-4-isothiocyanate was purchased from Dojin Chemical Co. Ltd

Syntheses of 2-substituted 1-amino-4-bromoanthraquinones (bromaminic acid analogues) – precursors for dyes and drugs

• Enas M. Malik,
• Younis Baqi and
• Christa E. Müller

Beilstein J. Org. Chem. 2015, 11, 2326–2333, doi:10.3762/bjoc.11.253

• formaldehyde under alkaline conditions to yield 1-amino-2-hydroxymethylanthraquinone (5) in good isolated yield [56] (Scheme 2). Compound 5 was subjected to bromination using bromine in N,N-dimethylformamide (DMF). The reaction proceeded smoothly at room temperature affording 1-amino-4-bromo-2

Dimethylamine as the key intermediate generated in situ from dimethylformamide (DMF) for the synthesis of thioamides

• Weibing Liu,
• Cui Chen and
• Hailing Liu

Beilstein J. Org. Chem. 2015, 11, 1721–1726, doi:10.3762/bjoc.11.187

• ., Haidian District, Beijing 100875, P. R. China; Tel: +86-15010928428 10.3762/bjoc.11.187 Abstract An improved and efficient method for the synthesis of thioamides is presented. For this transformation, dimethylamine as the key intermediate is generated in situ from dimethylformamide (DMF). All the tested

• substrates produced the desired products with excellent isolated yields. Keywords: aldehydes; dimethylformamide (DMF); elemental sulfur; ketones; thioamides; Introduction Thioamides, a well-known structural element of many sulfur-containing molecules, synthetic agents [1][2], heterocycles, natural products

Qualitative evaluation of regioselectivity in the formation of di- and tri-6-O-tritylates of α-cyclodextrin

• Keisuke Yoshikiyo,
• Yoshihisa Matsui and
• Tatsuyuki Yamamoto

Beilstein J. Org. Chem. 2015, 11, 1530–1540, doi:10.3762/bjoc.11.168

• pyridine was dried over CaH2 and distilled in the presence of CaH2 before use. N,N-Dimethylformamide (DMF) was also dried over CaH2 and distilled before use. Acetonitrile for high performance liquid chromatography was purchased from Wako Pure Chemical Industries Ltd. DMSO-d6 containing 0.05% v/v

Synthesis and evaluation of the biostability and cell compatibility of novel conjugates of nucleobase, peptidic epitope, and saccharide

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum,
• Khalid Omar Al Footy,
• Khadija Omar Badahdah and
• Bing Xu

Beilstein J. Org. Chem. 2015, 11, 1352–1359, doi:10.3762/bjoc.11.145

• dimethylformamide (DMF) to expose the amino group. The second amino acid, Fmoc-Pro-OH, was reacted with the free amino group using the coupling reagent N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate/N,N-diisopropylethylamine (HBTU/DIPEA). The elongation of the peptide chain was done by

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

• Rupert G. D. Taylor,
• Joseph Cameron,
• Iain A. Wright,
• Neil Thomson,
• Olena Avramchenko,
• Alexander L. Kanibolotsky,
• Anto R. Inigo,
• Tell Tuttle and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

• poor solubility of 5 in common organic solvents. However, under microwave conditions successful couplings could be readily achieved in dimethylformamide (DMF) at 160 °C (Scheme 2). It is noteworthy that in both cases no partially substituted TTFs were observed as reaction byproducts (due to the

Quarternization of 3-azido-1-propyne oligomers obtained by copper(I)-catalyzed azide–alkyne cycloaddition polymerization

• Shun Nakano,
• Akihito Hashidzume and
• Takahiro Sato

Beilstein J. Org. Chem. 2015, 11, 1037–1042, doi:10.3762/bjoc.11.116

• gradient pulse was rectangular, and its strength varied automatically during the course of the experiments. 3-Bromo-1-propyne (BrP), sodium azide (NaN3), N,N-dimethylformamide (DMF), copper sulfate pentahydrate (CuSO4·5H2O), (+)-sodium L-ascorbate (NaAsc), and methyl iodide were purchased from Wako Pure

A versatile δ-aminolevulinic acid (ΑLA)-cyclodextrin bimodal conjugate-prodrug for PDT applications with the help of intracellular chemistry

• Chrysie Aggelidou,
• Theodossis A. Theodossiou,
• Antonio Ricardo Gonçalves,
• Mariza Lampropoulou and
• Konstantina Yannakopoulou

Beilstein J. Org. Chem. 2014, 10, 2414–2420, doi:10.3762/bjoc.10.251

• acid with heptakis(6-hydroxyethylamino-6-deoxy)-β-cyclodextrin (9). Heptakis(6-hydroxyethylamino-6-deoxy)-β-cyclodextrin (4, 62 mg, 0.043 mmol) was dissolved in dimethylformamide (DMF, 2 mL), cooled to 0 °C and stirred for 15 min. Then, 4-dimethylaminopyridine (DMAP, 3.7 mg, 0.0302 mmol) and Ν,Ν

Synthesis of novel conjugates of a saccharide, amino acids, nucleobase and the evaluation of their cell compatibility

• Dan Yuan,
• Xuewen Du,
• Junfeng Shi,
• Ning Zhou,
• Abdulgader Ahmed Baoum and
• Bing Xu

Beilstein J. Org. Chem. 2014, 10, 2406–2413, doi:10.3762/bjoc.10.250

• -Asp (20). After loading the first amino acid (Fmoc-Asp(Ot-Bu)-OH) on the 2-chlorotrityl chloride resin, we blocked the resin by dichloromethane (DCM)/methanol (MeOH)/N,N-diisopropylethylamine (DIEA) (8:1.5:0.5), next removed the Fmoc protecting group by 20% piperidine in N,N-dimethylformamide (DMF

Phosphinocyclodextrins as confining units for catalytic metal centres. Applications to carbon–carbon bond forming reactions

• Matthieu Jouffroy,
• Rafael Gramage-Doria,
• David Sémeril,
• Dominique Armspach,
• Dominique Matt,
• Werner Oberhauser and
• Loïc Toupet

Beilstein J. Org. Chem. 2014, 10, 2388–2405, doi:10.3762/bjoc.10.249

• styrene and aryl bromides using [Pd(OAc)2] (OAc = acetate) as a palladium source [65]. In a preliminary study, 4-bromoanisole was reacted for 1 h with styrene in N,N-dimethylformamide (DMF) in the presence of Cs2CO3 (Table 3). The runs were carried out at different temperatures and L:M ratios. The highest

The effect of permodified cyclodextrins encapsulation on the photophysical properties of a polyfluorene with randomly distributed electron-donor and rotaxane electron-acceptor units

• Aurica Farcas,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert,
• Flavian Farcas,
• Iuliana Stoica and
• Anton Airinei

Beilstein J. Org. Chem. 2014, 10, 2145–2156, doi:10.3762/bjoc.10.222

• )4], β-CD and γ-CD, bromobenzene (Br–Ph), dimethylformamide (DMF), and dimethyl sulfoxide (DMSO) were purchased from (Sigma-Aldrich) and used as received. Malononitrile (Merck), tetrabutylammonium perchlorate (TBAP) for electrochemical analysis (99.0%) (Fluka) were used without further purification

Photorelease of phosphates: Mild methods for protecting phosphate derivatives

• Sanjeewa N. Senadheera,
• Abraham L. Yousef and
• Richard S. Givens

Beilstein J. Org. Chem. 2014, 10, 2038–2054, doi:10.3762/bjoc.10.212

• conditions used for the photolysis of the esters. Photolysis samples were analyzed for product formation and ester disappearance using 1H NMR and RP-HPLC methods. Dimethylformamide (DMF, 2 μL, 2.6 × 10−2 mmol) was used as an internal standard in 1H NMR analyses. For HPLC analyses the solvent was 70% CH3CN

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

• dimethylformamide (DMF) and act as complexing agents towards a series of anions (Cl−, Br−, I−, NO3−, HSO4−). The crystal structures of 3, 2·2DMSO, 2·2DMF, and of the complex NEt4[Br·2] have been determined. Quantitative investigations of the complexation equilibria were performed via 1H NMR titrations. While 1 is a

• 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

A promising cellulose-based polyzwitterion with pH-sensitive charges

• Thomas Elschner and
• Thomas Heinze

Beilstein J. Org. Chem. 2014, 10, 1549–1556, doi:10.3762/bjoc.10.159

• of (3-ethoxy-3-oxopropyl)(N-Boc-2-aminoethyl)cellulose carbamate 4 In a centrifuge tube β-alanine ethyl ester hydrochloride (11.27 g, 73 mmol) dissolved in 70 mL N,N-dimethylformamide (DMF) and a solution of triethylamine (5.93 g, 59 mmol) in 20 mL DMF was added. The tube was shaken immediately and

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