Cyclodextrins tethered with oligolactides – green synthesis and structural assessment

• Cristian Peptu,
• Mihaela Balan-Porcarasu,
• Alena Šišková,
• Ľudovít Škultéty and
• Jaroslav Mosnáček

Beilstein J. Org. Chem. 2017, 13, 779–792, doi:10.3762/bjoc.13.77

• ) spectroscopy, however, in case of CD-oligolactides no such structural proofs were presented. Later, the LA was polymerized in dimethylformamide (DMF) solution to result in well-defined and homogenous β-CD functionalized with oligolactides as demonstrated by electrospray mass spectrometry (ESI–MS) and NMR

Continuous-flow synthesis of highly functionalized imidazo-oxadiazoles facilitated by microfluidic extraction

• Ananda Herath and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2017, 13, 239–246, doi:10.3762/bjoc.13.26

• using polar organic solvents such as dimethylformamide (DMF) [7][8][9][15]. However, the challenges of removing large amounts of high boiling solvents during the purification and isolation process can limit scalability and efficiency. Furthermore, many useful synthetic reactions are incompatible with

• reaction conditions using a single microreactor we found that the combination of EDC/HOBt/DIPEA (1:1:1) for 10 min at 150 °C provided the best conditions for complete conversion of 3-bromobenzoic acid to the corresponding 1,2,4-oxadiazole derivative (Table 1, entry 5). The use of N,N-dimethylformamide (DMF

Electron-transfer-initiated benzoin- and Stetter-like reactions in packed-bed reactors for process intensification

• Anna Zaghi,
• Daniele Ragno,
• Graziano Di Carmine,
• Carmela De Risi,
• Olga Bortolini,
• Pier Paolo Giovannini,
• Giancarlo Fantin and
• Alessandro Massi

Beilstein J. Org. Chem. 2016, 12, 2719–2730, doi:10.3762/bjoc.12.268

• -unsaturated acceptors [27][28][29]. Indeed, activation of aromatic α-diketones may occur through a double electron-transfer (ET) process triggered by the carbamoyl anion derived from N,N-dimethylformamide (DMF) solvent with catalytic base, which generates an enediolate anion as key reactive species of

• heterogeneous continuous-flow procedure for the polarity reversal of aromatic α-diketones is presented. Propaedeutic batch experiments have been initially performed to select the optimal supported base capable to initiate the two electron-transfer process from the carbamoyl anion of the N,N-dimethylformamide

• (DMF) solvent to the α-diketone and generate the corresponding enediolate active species. After having identified the 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine on polystyrene (PS-BEMP) as the suitable base, packed-bed microreactors (pressure-resistant stainless-steel

Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

• Laszlo Jicsinszky,
• Marina Caporaso,
• Katia Martina,
• Emanuela Calcio Gaudino and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2016, 12, 2364–2371, doi:10.3762/bjoc.12.230

• as sodium hydride, to activate the thiol group of 3-mercaptopropionic acid (MPA) and N,N-dimethylformamide (DMF) [16]. In the reaction solution and particularly on larger scales (from 10 g to kilo lab scale), impurities that arise from incomplete conversions, product and byproduct decomposition as

Rapid regio- and multi-coupling reactivity of 2,3-dibromobenzofurans with atom-economic triarylbismuths under palladium catalysis

• Maddali L. N. Rao,
• Jalindar B. Talode and
• Venneti N. Murty

Beilstein J. Org. Chem. 2016, 12, 2065–2076, doi:10.3762/bjoc.12.195

• -dimethylformamide (DMF) and N,N-dimethylacetamide (DMA) furnished lowered yields (Table 1, entries 6 and 7) in comparison with NMP solvent. Carrying out the cross-couplings at different temperatures also gave lower yields (Table 1, entries 8 and 9). Additionally, the stoichiometric combination of 3 equiv of 2,3

Hydroxy-functionalized hyper-cross-linked ultra-microporous organic polymers for selective CO₂ capture at room temperature

• Partha Samanta,
• Priyanshu Chandra and
• Sujit K. Ghosh

Beilstein J. Org. Chem. 2016, 12, 1981–1986, doi:10.3762/bjoc.12.185

• -(hydroxymethyl)anthracene, respectively (Figure 1). HCP-91 and HCP-94 have been synthesized by using a Friedel–Crafts alkylation reaction. The thus obtained as-synthesized compounds were washed repeatedly with dimethylformamide (DMF), methanol, water, chloroform, dichloromethane and tetrahydrofuran (THF) to

TMSBr-mediated solvent- and work-up-free synthesis of α-2-deoxyglycosides from glycals

• Mei-Yuan Hsu,
• Yi-Pei Liu,
• Sarah Lam,
• Su-Ching Lin and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2016, 12, 1758–1764, doi:10.3762/bjoc.12.164

• , dimethylformamide (DMF) (64%, Table 2, entry 2) [76], acetonitrile (ACN) [74] (44%, Table 2, entry 3), tetrahydrofuran (THF) (56%, Table 2, entry 4), and dioxane [75] (50%, Table 2, entry 5) were tested as glycosylation modulators and similar yields of 25 were obtained, but their α-selectivities dramatically

Rh-Catalyzed reductive Mannich-type reaction and its application towards the synthesis of (±)-ezetimibe

• Motoyuki Isoda,
• Kazuyuki Sato,
• Yurika Kunugi,
• Satsuki Tokonishi,
• Atsushi Tarui,
• Masaaki Omote,
• Hideki Minami and
• Akira Ando

Beilstein J. Org. Chem. 2016, 12, 1608–1615, doi:10.3762/bjoc.12.157

• 0.25 mm × 15 m, carrier; He). Peak areas were calculated on a Hitachi D-2500 Chromato-Integrator. Materials Tetrahydrofuran (THF) was purchased from Kanto Chemical Co. Inc. (Tokyo, Japan) in the dehydrated form. N,N-Dimethylformamide (DMF) and dichloromethane (CH2Cl2) were distilled over CaH2 and

Flow carbonylation of sterically hindered ortho-substituted iodoarenes

• Carl J. Mallia,
• Gary C. Walter and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2016, 12, 1503–1511, doi:10.3762/bjoc.12.147

• . Interestingly the addition of up to 20 mol % of dimethylformamide (DMF) as an additive did not improve the yield which had been suggested by evaluation of similar reactions in the literature [6][10]. However as anticipated, an increase in carbon monoxide pressure did pertain to a raise in product yield to 62

Mycothiol synthesis by an anomerization reaction through endocyclic cleavage

• Shino Manabe and
• Yukishige Ito

Beilstein J. Org. Chem. 2016, 12, 328–333, doi:10.3762/bjoc.12.35

• -disaccharide 2 in 90% yield (Scheme 4). After removing the phthaloyl and acetyl groups by using ethylenediamine in dimethylformamide (DMF), a carbamate group was introduced using triphosgene in the presence of NaHCO3. Acetylation of both the hydroxy and carbamate groups was carried out using acetic anhydride

Synthesis and photophysical characteristics of polyfluorene polyrotaxanes

• Aurica Farcas,
• Giulia Tregnago,
• Ana-Maria Resmerita,
• Pierre-Henri Aubert and
• Franco Cacialli

Beilstein J. Org. Chem. 2015, 11, 2677–2688, doi:10.3762/bjoc.11.288

• the generation of active layers in organic electronic devices. Experimental Materials and methods 1, 2, tetrakis(triphenylphosphine)palladium(0) [Pd(PPh3)4], β- and γCD, bromobenzene (Br–Ph), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), and quinine sulfate dehydrate in 0.5 M sulfuric acid were

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