Inclusion of trans-resveratrol in methylated cyclodextrins: synthesis and solid-state structures

• Lee Trollope,
• Dyanne L. Cruickshank,
• Terence Noonan,
• Susan A. Bourne,
• Milena Sorrenti,
• Laura Catenacci and
• Mino R. Caira

Beilstein J. Org. Chem. 2014, 10, 3136–3151, doi:10.3762/bjoc.10.331

• with a DSC821e Module and an Intracooler device for sub-ambient temperature analysis (Julabo FT 900) on 2–4 mg (Mettler M3 Microbalance) samples in sealed aluminium pans with pierced lid [heating rate β = 10 K min−1, nitrogen atmosphere (flux 50 mL min−1), 30–350 °C temperature range)]. The instrument

• was previously calibrated with indium as standard reference. Measurements were carried out at least in triplicate. For co-precipitated, crystalline products, traces were recorded on a DSC-Q200 differential scanning calorimeter with samples in closed aluminium pans heated at 10 K min−1 and dry nitrogen

Removal of volatile organic compounds using amphiphilic cyclodextrin-coated polypropylene

• Ludmilla Lumholdt,
• Sophie Fourmentin,
• Thorbjørn T. Nielsen and
• Kim L. Larsen

Beilstein J. Org. Chem. 2014, 10, 2743–2750, doi:10.3762/bjoc.10.290

• were introduced into 20 mL glass vials and sealed with a silicone septum and aluminium foil and left overnight. Measurements were conducted with an Agilent G1888 headspace autosampler. A 1 mL sample was withdrawn from the vial using a gas-tight syringe and injected directly into the chromatography

Solution processable diketopyrrolopyrrole (DPP) cored small molecules with BODIPY end groups as novel donors for organic solar cells

• Diego Cortizo-Lacalle,
• Calvyn T. Howells,
• Upendra K. Pandey,
• Joseph Cameron,
• Neil J. Findlay,
• Anto Regis Inigo,
• Tell Tuttle,
• Peter J. Skabara and
• Ifor D. W. Samuel

Beilstein J. Org. Chem. 2014, 10, 2683–2695, doi:10.3762/bjoc.10.283

• deposition. 20 nm of calcium and 200 nm of aluminium were thermally evaporated at a base pressure of 2 × 10−6 mbar. Devices were then encapsulated with a glass cover slip and a UV curable optical adhesive from Thorlabs. The active area of the devices was 6 mm2. Characterisation was performed in air using a

Preparation of neuroprotective condensed 1,4-benzoxazepines by regio- and diastereoselective domino Knoevenagel–[1,5]-hydride shift cyclization reaction

• László Tóth,
• Yan Fu,
• Hai Yan Zhang,
• Attila Mándi,
• Katalin E. Kövér,
• Tünde-Zita Illyés,
• Attila Kiss-Szikszai,
• Balázs Balogh,
• Tibor Kurtán,
• Sándor Antus and
• Péter Mátyus

Beilstein J. Org. Chem. 2014, 10, 2594–2602, doi:10.3762/bjoc.10.272

• C15H13NO2Na, 262.0844; found, 262.0839; Anal. calcd for C15H13NO2 (239.09): C, 75.30; H, 5.48; N, 5.85; found: C, 75.28; H, 5.49; N, 5.85. 2-Phenyl-2,3,4,5-tetrahydro-1,4-benzoxazepine (rac-10): To a stirred solution of rac-9 (8.13 g, 33.98 mmol) in dry THF (80 mL), 2.0 M lithium aluminium hydride solution in

Synthesis and biological evaluation of novel N-α-haloacylated homoserine lactones as quorum sensing modulators

• Michail Syrpas,
• Ewout Ruysbergh,
• Christian V. Stevens,
• Norbert De Kimpe and
• Sven Mangelinckx

Beilstein J. Org. Chem. 2014, 10, 2539–2549, doi:10.3762/bjoc.10.265

• appropriate acid chloride 2 (5 mmol) which was kept under a nitrogen atmosphere at 0 °C, P(OMe)3 (1.16 equiv, 1.45 mL, 5.8 mmol) was added. The mixture was stirred for 4 h at room temperature. Then the excess of P(OMe)3 and MeCl were evaporated under reduced pressure. The flask was covered with aluminium foil

Synthesis and immunological evaluation of protein conjugates of Neisseria meningitidis X capsular polysaccharide fragments

• Laura Morelli,
• Damiano Cancogni,
• Marta Tontini,
• Alberto Nilo,
• Sara Filippini,
• Paolo Costantino,
• Maria Rosaria Romano,
• Francesco Berti,
• Roberto Adamo and
• Luigi Lay

Beilstein J. Org. Chem. 2014, 10, 2367–2376, doi:10.3762/bjoc.10.247

• all animal studies. For the formulation of the vaccines, to a volume of glycoconjugate corresponding to 0.3 μg or 1 μg/dose) aluminium phosphate (100 μl of a solution 1.2 mg/mL, 120 μg/dose) was added. The final volume of the formulation was diluted to 200 μL/dose by addition of PBS pH 7.2 buffer. An

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

• -caprolactam (2) A mixture of 40 g (219 mmol) of L-lysine monohydrochloride (1), 8.76 g (219 mmol) sodium hydroxide, 120 g (1.178 mol) aluminium oxide and 450 ml of n-butanol is heated to reflux for 48 h in a reaction vessel equipped with a water trap. Subsequently, the mixture is filtrated and the obtained

Convergent synthetic methodology for the construction of self-adjuvanting lipopeptide vaccines using a novel carbohydrate scaffold

• Vincent Fagan,
• Istvan Toth and
• Pavla Simerska

Beilstein J. Org. Chem. 2014, 10, 1741–1748, doi:10.3762/bjoc.10.181

• absence of other important immuno-stimulatory components, known as adjuvants [4]. Adjuvant development has advanced slowly and for many decades, aluminium salts were the only adjuvants approved for clinical use [5]. Recently, research efforts have focused on the development of adjuvants which activate

The search for new amphiphiles: synthesis of a modular, high-throughput library

• George C. Feast,
• Thomas Lepitre,
• Xavier Mulet,
• Charlotte E. Conn,
• Oliver E. Hutt,
• G. Paul Savage and
• Calum J. Drummond

Beilstein J. Org. Chem. 2014, 10, 1578–1588, doi:10.3762/bjoc.10.163

• amphiphile–water interface and thus move towards desired inverse phase formation. Experimental General procedure for the synthesis of amphiphiles. To each of 24 glass vials (18 mm × 45 mm) in a 4 × 6 array aluminium reaction block, was added a solution of azido-sugar (1.0 equiv, ca. 15 mg) in 2:1 t-BuOH

Unusual polymorphism in new bent-shaped liquid crystals based on biphenyl as a central molecular core

• Anna Kovářová,
• Svatopluk Světlík,
• Václav Kozmík,
• Jiří Svoboda,
• Vladimíra Novotná,
• Damian Pociecha,
• Ewa Gorecka and
• Natalia Podoliak

Beilstein J. Org. Chem. 2014, 10, 794–807, doi:10.3762/bjoc.10.75

• in X-ray measurements. Experimental Measurements All compounds were studied using differential scanning calorimetry (DSC). The materials of 2–5 mg were hermetically closed in the aluminium pans and placed in nitrogen atmosphere of a Perkin–Elmer Pyris Diamond calorimeter. Cooling and heating rates of

Asymmetric total synthesis of a putative sex pheromone component from the parasitoid wasp Trichogramma turkestanica

• Danny Geerdink,
• Jeffrey Buter,
• Teris A. van Beek and
• Adriaan J. Minnaard

Beilstein J. Org. Chem. 2014, 10, 761–766, doi:10.3762/bjoc.10.71

• flash-column chromatography over either silica gel or neutral aluminium oxide, however, led to rapid degradation of 2. In the process, we were unable to isolate a pure sample of either isomer. This approach was ultimately abandoned, and only delivered the knowledge that 2 is unstable upon purification

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

• enhance the solvating properties of the scCO2. The 60 mL autoclave was charged with 2.4 mL of the reaction solution, corresponding to 4% of the autoclave volume. 2% Palladium on a silica support catalyst (20.4 mg, 2.463 mmol) was then added and the autoclave sealed and inserted into a pre-heated aluminium

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

• apparatus was set under constant nitrogen-flow and 17.2 mmol of sodium hydride were added. Afterwards, the suspension was stirred for 2 h and subsequently, 35 mmol of allyl bromide (4), which was filtrated through neutral aluminium oxide, was added dropwise. The resulting mixture was stirred at 50 °C for 18

Oligomeric epoxide–amine adducts based on 2-amino-N-isopropylacetamide and α-amino-ε-caprolactam: Solubility in presence of cyclodextrin and curing properties

• Julian Fischer and
• Helmut Ritter

Beilstein J. Org. Chem. 2013, 9, 2803–2811, doi:10.3762/bjoc.9.315

• (acetone) m/z: 117.1 [M + H]+. Synthesis of 7 [22]: A mixture of 20 g (109.5 mmol) L-lysine monohydrochloride (6), 4.38 g (109.5 mmol) sodium hydroxide, 60 g (589 mmol) aluminium oxide and 300 mL n-butanol is heated to reflux for 48 h in a reaction vessel equipped with a water trap. Subsequently, the

New syntheses of 5,6- and 7,8-diaminoquinolines

• Maroš Bella and
• Viktor Milata

Beilstein J. Org. Chem. 2013, 9, 2669–2674, doi:10.3762/bjoc.9.302

• heterocycles. Experimental General. Thin-layer chromatography (TLC) was performed on aluminium plates precoated with 0.2 mm silica gel (25 μm) containing fluorescent indicator 254 nm (Fluka) and stains were visualised by UV light (254 nm or 366 nm). Flash liquid chromatography (FLC) was performed on silica gel

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

• times causes problems during work-up, especially in larger scale reactions. We, among others, have observed the gelatinous aluminium salts after the addition of an aqueous solution. Due to the formation of insoluble gel-like aluminium salts, the extraction procedure gets more challenging and sometimes a

• small portion of the substrate remains with the aluminium salts. Another drawback of DIBAL-H is the overreduction to alcohol 6. When only small amounts of the overreduced alcohol are present, one high vacuum distillation is enough to purify the crude aldehyde. When present in amounts greater than 10

A combined continuous microflow photochemistry and asymmetric organocatalysis approach for the enantioselective synthesis of tetrahydroquinolines

• Erli Sugiono and
• Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 2457–2462, doi:10.3762/bjoc.9.284

• programmable syringe pump. The product solution was collected in a flask wrapped with aluminium foil to prevent further irradiation. Our initial investigation of reaction conditions involved the photocyclization–reduction cascade of 2-aminochalcone 1a in the presence of Hantzsch dihydropyridine 4 as hydrogen

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

• moderate yield the benzoxazine 1.118; via the imine intermediate. This material can then be condensed with diethyl ethoxymethylenemalonate (1.123), and further cyclised via an intramolecular Friedel–Crafts acylation promoted by polyphosphate. Aluminium tribromide assisted demethylation of the pendant

Elucidation of the regio- and chemoselectivity of enzymatic allylic oxidations with Pleurotus sapidus – conversion of selected spirocyclic terpenoids and computational analysis

• Verena Weidmann,
• Mathias Schaffrath,
• Holger Zorn,
• Julia Rehbein and
• Wolfgang Maison

Beilstein J. Org. Chem. 2013, 9, 2233–2241, doi:10.3762/bjoc.9.262

• the literature protocol using m-chloroperbenzoic acid. The major epoxide 4a was obtained in good yield and a diastereoselectivity of 11:1. Isomerisation of epoxide 4a to allyl alcohol 22 was reported with aluminium triisopropoxide at 140 °C [46]. However, in our hands this procedure gave only complex

Regioselective 1,4-trifluoromethylation of α,β-unsaturated ketones via a S-(trifluoromethyl)diphenylsulfonium salts/copper system

• Satoshi Okusu,
• Yutaka Sugita,
• Etsuko Tokunaga and
• Norio Shibata

Beilstein J. Org. Chem. 2013, 9, 2189–2193, doi:10.3762/bjoc.9.257

• aluminium-centered Lewis acid with low to moderate yields [18]. Dilman and co-workers partially overcame this problem by using highly electrophilic alkenes bearing either Meldrum’ acids [19], or two geminal nitrile groups [20]. However, direct 1,4-trifluoromethylation to conventional α,β-unsaturated ketones

Continuous flow photocyclization of stilbenes – scalable synthesis of functionalized phenanthrenes and helicenes

• Quentin Lefebvre,
• Marc Jentsch and
• Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 1883–1890, doi:10.3762/bjoc.9.221

• enhance the efficiency of irradiation by reflection, the setup was placed into a laboratory Dewar flask and the exposed parts of the setup were covered with aluminium foil (the temperature inside the Dewar was determined to be around 40 °C). The reaction mixture was injected into the system using a

The first example of the Fischer–Hepp type rearrangement in pyrimidines

• Inga Cikotiene,
• Mantas Jonusis and
• Virginija Jakubkiene

Beilstein J. Org. Chem. 2013, 9, 1819–1825, doi:10.3762/bjoc.9.212

• aluminium plates (Merck). Visualization was accomplished by UV light. Preparation of the starting materials 1, N-nitrosation and denitrosation reactions were performed according the methods published earlier [15][16]. Typical one-pot nucleophilic substitution–rearrangement procedure. A solution of the

A Lewis acid-promoted Pinner reaction

• Dominik Pfaff,
• Gregor Nemecek and
• Joachim Podlech

Beilstein J. Org. Chem. 2013, 9, 1572–1577, doi:10.3762/bjoc.9.179

•  1, entries 2 and 3). The 3% yield in acetonitrile/water (10:1) suggests that water is detrimental in the Pinner reaction. Among various tested Lewis acids, the best results were obtained with aluminium tribromide at 50 °C (65%, Table 1, entry 5) and with trimethylsilyl triflate at room temperature

• (83%, Table 1, entry 7). The less expensive trimethylsilyl chloride turned out to be an unsuitable alternative (Table 1, entry 8). The yield could not be improved, when two equivalents of aluminium bromide were used together with catalytic amounts of hafnium triflate (Table 1, entry 6). Since two

Space filling of β-cyclodextrin and β-cyclodextrin derivatives by volatile hydrophobic guests

• Sophie Fourmentin,
• Anca Ciobanu,
• David Landy and
• Gerhard Wenz

Beilstein J. Org. Chem. 2013, 9, 1185–1191, doi:10.3762/bjoc.9.133

• solutions of 10 mL containing 1 ppm of guest were introduced into 20 mL headspace vials and sealed by using a silicone septa and aluminium foil. The vials were then thermostated at 25 ± 0.1 °C. After the equilibrium had been established (30 min), 1 mL of vapor from the above solution was withdrawn from the

Synthesis of the tetracyclic core of Illicium sesquiterpenes using an organocatalyzed asymmetric Robinson annulation

• Lynnie Trzoss,
• Jing Xu,
• Michelle H. Lacoske and
• Emmanuel A. Theodorakis

Beilstein J. Org. Chem. 2013, 9, 1135–1140, doi:10.3762/bjoc.9.126

• under Meerwein’s conditions to afford β-ketoester 17. Treatment of 17 with TMSOTf/Et3N followed by enolate alkylation [82] under TBAF/MeI conditions afforded the desired C-5 quaternary center of 18 as a single isomer (35% over four steps). Global reduction of 18 with lithium aluminium hydride produced