The synthesis of α-aryl-α-aminophosphonates and α-aryl-α-aminophosphine oxides by the microwave-assisted Pudovik reaction

• Erika Bálint,
• Ádám Tajti,
• Anna Ádám,
• István Csontos,
• Konstantin Karaghiosoff,
• Mátyás Czugler,
• Péter Ábrányi-Balogh and
• György Keglevich

Beilstein J. Org. Chem. 2017, 13, 76–86, doi:10.3762/bjoc.13.10

• plates was dissected and used for X-ray measurement at low temperatures. There seems to be a slight disorder, which becomes evident in the ellipsoids of the aniline ring and one of the methyl carbon atoms (Figure 4). The crystal structure of compound 5b was published almost 40 years ago [61], and a

Synthesis of multi-lactose-appended β-cyclodextrin and its cholesterol-lowering effects in Niemann–Pick type C disease-like HepG2 cells

• Keiichi Motoyama,
• Rena Nishiyama,
• Yuki Maeda,
• Taishi Higashi,
• Yoichi Ishitsuka,
• Yuki Kondo,
• Tetsumi Irie,
• Takumi Era and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2017, 13, 10–18, doi:10.3762/bjoc.13.2

• NPC-like HepG2 cells via asialoglycoprotein receptor (ASGPR)-mediated endocytosis. Keywords: asialoglycoprotein receptor; cholesterol; cyclodextrin; lactose; Niemann–Pick type C disease; Introduction The Niemann–Pick type C (NPC) disease is a lipid storage disorder with the accumulation of membrane

From betaines to anionic N-heterocyclic carbenes. Borane, gold, rhodium, and nickel complexes starting from an imidazoliumphenolate and its carbene tautomer

• Ming Liu,
• Jan C. Namyslo,
• Martin Nieger,
• Mika Polamo and
• Andreas Schmidt

Beilstein J. Org. Chem. 2016, 12, 2673–2681, doi:10.3762/bjoc.12.264

• . peak/hole = 0.404/−0.489 e Å−3, disorder of the halogen counter anion (occupancy Cl/Br 0.813(2):0.187(2)). 11: yellow crystals, C39H45N6O3Rh, Mr = 748.72, crystal size 0.38 × 0.32 × 0.16 mm, monoclinic, space group P21/n (No. 14), a = 11.7692(5) Å, b = 18.8111(7) Å, c = 16.2459(7) Å, β = 104.615(2)°, V

• , disorder of the n-butyl group. 12: yellow crystals, C26H30N4NiO2∙H2O, Mr = 507.26, crystal size 0.22 × 0.12 × 0.04 mm, monoclinic, space group P21/n (No. 14), a = 11.2267(5) Å, b = 22.8310(9) Å, c = 19.1274(8) Å, β = 100.099(2)°, V = 4826.7(4) Å3, Z = 8, ρ = 1.396 Mg/m−3, µ(Mo Kα) = 0.839 mm−1, F(000

• ; crystallographic numbering). Molecular drawing of rhodium complex 11 (minor disorder parts omitted for clarity, displacement parameters are drawn at 50% probability level; crystallographic numberings). Molecular drawing of the dimeric nickel complex 12 (displacement parameters are drawn at 50% probability level

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

Combined experimental and theoretical studies of regio- and stereoselectivity in reactions of β-isoxazolyl- and β-imidazolyl enamines with nitrile oxides

• Ilya V. Efimov,
• Marsel Z. Shafikov,
• Nikolai A. Beliaev,
• Natalia N. Volkova,
• Tetyana V. Beryozkina,
• Wim Dehaen,
• Zhijin Fan,
• Viktoria V. Grishko,
• Gert Lubec,
• Pavel A. Slepukhin and
• Vasiliy A. Bakulev

Beilstein J. Org. Chem. 2016, 12, 2390–2401, doi:10.3762/bjoc.12.233

• in the literature in comparison with monocyclic and fused derivatives [1][6]. Recently isoxazoles conjugated to pyrazole A [12], imidazole B [13] and tetrazole C [4] rings were found as promising candidates for anticancer and antidiabetic drugs and for the treatment of cognitive disorder (Figure 1

Comparing blends and blocks: Synthesis of partially fluorinated diblock polythiophene copolymers to investigate the thermal stability of optical and morphological properties

• Pierre Boufflet,
• Sebastian Wood,
• Jessica Wade,
• Zhuping Fei,
• Ji-Seon Kim and
• Martin Heeney

Beilstein J. Org. Chem. 2016, 12, 2150–2163, doi:10.3762/bjoc.12.205

• such temperatures, and thus result in increased absorption in the high-energy region. It is interesting to note that the vibronic structure is more resistant to higher annealing temperatures in the blends, perhaps indicating that in the block copolymers the disorder of the melted P3OT sections help

Effect of the π-conjugation length on the properties and photovoltaic performance of A–π–D–π–A type oligothiophenes with a 4,8-bis(thienyl)benzo[1,2-b:4,5-b′]dithiophene core

• Ni Yin,
• Lilei Wang,
• Yi Lin,
• Jinduo Yi,
• Lingpeng Yan,
• Junyan Dou,
• Hai-Bo Yang,
• Xin Zhao and
• Chang-Qi Ma

Beilstein J. Org. Chem. 2016, 12, 1788–1797, doi:10.3762/bjoc.12.169

• broad absorption band peaking at 494, 491, and 485 nm, respectively, while two absorption bands peaking at 440 and 498 nm were found for 1. Elongation of the π-conjugated bridge leads to a slight hypochromic shift of the absorption band, presumably ascribed to a disorder of the complex structures of the

Synthesis of ferrocenyl-substituted 1,3-dithiolanes via [3 + 2]-cycloadditions of ferrocenyl hetaryl thioketones with thiocarbonyl S-methanides

• Grzegorz Mlostoń,
• Róża Hamera-Fałdyga,
• Anthony Linden and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2016, 12, 1421–1427, doi:10.3762/bjoc.12.136

• 5b and 5f (with 50% probability ellipsoids; arbitrary numbering of the atoms; only the major disorder conformation of the selenophene ring is shown). Reactions of aromatic thiocarbonyl S-methanides 2a,b with ferrocenyl thioketones 1 (Table 1). Reactions of cycloaliphatic thiocarbonyl S-methanides

Exploring architectures displaying multimeric presentations of a trihydroxypiperidine iminosugar

• Camilla Matassini,
• Stefania Mirabella,
• Andrea Goti,
• Inmaculada Robina,
• Antonio J. Moreno-Vargas and
• Francesca Cardona

Beilstein J. Org. Chem. 2015, 11, 2631–2640, doi:10.3762/bjoc.11.282

• metabolic disorder and Helicobacter pylori infection, as well as in the elucidation of the biological role of α-L-fucosidase in spermiogenesis and sperm maturation [23]. Following our interest in the synthesis of natural alkaloids and their unnatural analogs we recently developed a straightforward synthetic

Inclusion complexes of 2-methoxyestradiol with dimethylated and permethylated β-cyclodextrins: models for cyclodextrin–steroid interaction

• Mino R. Caira,
• Susan A. Bourne,
• Halima Samsodien and
• Vincent J. Smith

Beilstein J. Org. Chem. 2015, 11, 2616–2630, doi:10.3762/bjoc.11.281

• host and guest during complexation [1]. Complex units A and B of TRIMEB·2ME, related by a pseudo-translation of ≈b/2, have nearly identical structural features, namely common TRIMEB host conformations and lack of host disorder, apparent twofold disorder of the 2ME methylene group at C6 (site-occupancy

• O19–H and a host glycosidic O4 atom (O···O 2.894(6) Å). This is evident in the cutaway diagram in Figure 4b. Complex unit C is unique in having neither host nor guest disorder and complex unit D also shows a unique feature, namely disorder in both the C- and D-rings of the 2ME molecule, which is thus

• present as two conformers in the ratio 0.61:0.39. One consequence of this is that there are two distinct positions for the O19–H phenolic group, each conformer forming a hydrogen bond with a different TRIMEB acceptor oxygen atom. Further details of this disorder and its implications are given below

Synthesis of racemic and chiral BEDT-TTF derivatives possessing hydroxy groups and their achiral and chiral charge transfer complexes

• Sara J. Krivickas,
• Chiho Hashimoto,
• Junya Yoshida,
• Akira Ueda,
• Kazuyuki Takahashi,
• John D. Wallis and
• Hatsumi Mori

Beilstein J. Org. Chem. 2015, 11, 1561–1569, doi:10.3762/bjoc.11.172

• )methyloxazoline)2X, (52X, X = AsF6 [7], PF6 [8]) where disorder within the racemic salt leads to lower conductivity. Recently, Pop et al., have also reported electrical magnetochiral anisotropy in chiral molecular conductors, (R,R)- and (S,S)-[dimethyl-(ethylenedithio)tetrathiafulvalene]2ClO4 (62ClO4) [9][10

Pd(OAc)₂-catalyzed dehydrogenative C–H activation: An expedient synthesis of uracil-annulated β-carbolinones

• Biplab Mondal,
• Somjit Hazra,
• Tarun K. Panda and
• Brindaban Roy

Beilstein J. Org. Chem. 2015, 11, 1360–1366, doi:10.3762/bjoc.11.146

• ]. For example, SL651498 was documented as a potential drug development candidate in a research program designed to discover subtype-selective GABAA receptor agonists for the treatment of muscle spasms and generalized anxiety disorder [13]. β-Carbolinones such as strychnocarpine, the alkaloid from

The chemical behavior of terminally tert-butylated polyolefins

• Dagmar Klein,
• Henning Hopf,
• Peter G. Jones,
• Ina Dix and
• Ralf Hänel

Beilstein J. Org. Chem. 2015, 11, 1246–1258, doi:10.3762/bjoc.11.139

• and angles were unrealistic. Possible sources of error would include disorder, unidentified weak reflections corresponding to a larger cell (the data were recorded on a serial diffractometer), or an incorrect space group. Refinements in lower symmetry space groups were, however, not better. We believe

Regioselective synthesis of chiral dimethyl-bis(ethylenedithio)tetrathiafulvalene sulfones

• Flavia Pop and
• Narcis Avarvari

Beilstein J. Org. Chem. 2015, 11, 1105–1111, doi:10.3762/bjoc.11.124

• ethylenedithiotetrathiafulvalene-oxazoline (EDT-TTF-Ox) donors [5][6], due to a structural disorder effect [7]. Evidence was thus provided, and confirmed later on with a second complete series of conducting salts based on the same donors [8], that the presence of chiral centers can modulate the structural disorder of radical

Indolizines and pyrrolo[1,2-c]pyrimidines decorated with a pyrimidine and a pyridine unit respectively

• Marcel Mirel Popa,
• Emilian Georgescu,
• Mino R. Caira,
• Florentina Georgescu,
• Constantin Draghici,
• Raluca Stan,
• Calin Deleanu and
• Florea Dumitrascu

Beilstein J. Org. Chem. 2015, 11, 1079–1088, doi:10.3762/bjoc.11.121

• are given in Supporting Information File 1. Structural refinements were non-routine owing to subtle disorder occurring in both crystals. Taking into account the values of Z (the number of molecules per unit cell) for the crystals of 6 and 8, their respective space groups, P21/n and P−1, require that

Donor–acceptor type co-crystals of arylthio-substituted tetrathiafulvalenes and fullerenes

• Xiaofeng Lu,
• Jibin Sun,
• Shangxi Zhang,
• Longfei Ma,
• Lei Liu,
• Hui Qi,
• Yongliang Shao and
• Xiangfeng Shao

Beilstein J. Org. Chem. 2015, 11, 1043–1051, doi:10.3762/bjoc.11.117

• measurements. In most cases, the fullerene molecules and solvent molecules are disordered. The disorder of fullerenes and solvents cannot be suppressed even at low temperature, and can thus be characterized as having statistic rather than rotational disorder. The selected crystallographic data are summarized

Design, synthesis and photochemical properties of the first examples of iminosugar clusters based on fluorescent cores

• Mathieu L. Lepage,
• Antoine Mirloup,
• Manon Ripoll,
• Fabien Stauffert,
• Anne Bodlenner,
• Raymond Ziessel and
• Philippe Compain

Beilstein J. Org. Chem. 2015, 11, 659–667, doi:10.3762/bjoc.11.74

• chaperones were thus disclosed in the field of Gaucher disease, the most common lysosomal storage disorder (Figure 1) [24][25]. DNJ clusters 2 and 3 are indeed able to increase mutant β-glucocerebrosidase (GCase) residual activity levels as much as 3.3-fold in cells of Gaucher patients at micromolar

Trifluoromethyl-substituted tetrathiafulvalenes

• Olivier Jeannin,
• Frédéric Barrière and
• Marc Fourmigué

Beilstein J. Org. Chem. 2015, 11, 647–658, doi:10.3762/bjoc.11.73

• EDT-TTF derivatives with either one ester (in 2ac) or one cyano group (in 2bc) in ortho position to the CF3 group. 2ac crystallizes in the monoclinic system, space group P21, with one molecule in general position in the unit cell (Figure 3), affected by disorder on the ethylene bridge. On the other

• positional disorder of the fluorine atoms, at variance with the other structures described above. Furthermore, the two ester groups are not coplanar, one of them lies flat with the TTF core while the other one is almost perpendicular. Charge-transfer complex and radical cation salt The relatively low

TTFs nonsymmetrically fused with alkylthiophenic moieties

• Rafaela A. L. Silva,
• Bruno J. C. Vieira,
• Marta M. Andrade,
• Isabel C. Santos,
• Sandra Rabaça,
• Dulce Belo and
• Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 628–637, doi:10.3762/bjoc.11.71

• orthorhombic system, space group P212121. The unit cell contains one independent molecule. The terminal sulfur atom presents an orientation disorder as denoted by two nearly identical occupation factors of 49% and 51% for S3 and S3A, respectively (Figure 2). This is most likely the result of orientation

• disorder of the molecule in the most stable trans configuration, rather than a cis–trans disorder. The bond lengths are within the expected range for thiophenic dithiol ketones [12][20]. The crystal structure is composed of pairs of side-by-side chains of ketone 1 running parallel to b. Within these bi

• present, in both molecules, an orientation disorder with occupation factors of 77 and 23% for the pair S8/S8A and 71 and 29% for the pair S1/S1A. The bond lengths of the molecule are within the expected range of values for neutral TTF derivatives [11]. The crystal structure is composed of layers of side

Attempts to prepare an all-carbon indigoid system

• Şeref Yildizhan,
• Henning Hopf and
• Peter G. Jones

Beilstein J. Org. Chem. 2015, 11, 363–372, doi:10.3762/bjoc.11.42

• observed (H5···π 2.76 Å, H9A···π 2.83 Å). The structure determination of 25 was of limited accuracy because of twinning and disorder problems (indeed, there may be a small amount of contamination by 24) and we therefore do not discuss it in detail. Both independent molecules display non-crystallographic

Novel biphenyl-substituted 1,2,4-oxadiazole ferroelectric liquid crystals: synthesis and characterization

• Mahabaleshwara Subrao,
• Dakshina Murthy Potukuchi,
• Girish Sharada Ramachandra,
• Poornima Bhagavath,
• Sangeetha G. Bhat and
• Srinivasulu Maddasani

Beilstein J. Org. Chem. 2015, 11, 233–241, doi:10.3762/bjoc.11.26

• phase is also noticed in the 13b (C12.Ox.C*Cn) series along with the 1D orthogonal SmA phase. Due to the presence of long chains on both sides of the oxadiazole core, the molecules are argued to favour [44][45][46] the orientational disorder, which leads to the stabilization of tilt layered structures

• orientational disorder in chiral LCs with flexible end chain on both sides. It is noticed that the isotropic temperatures are higher for the 13b (C12.Ox.C*Cn) series than the other phenyl substituted 13a homologs. Higher clearing temperatures are argued due to the chain geometry and close packing of the

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

• presence of guest disorder in two cases. An account of the key features of the inclusion of the RSV molecule within the respective host cavities as well as descriptions of the crystal packing arrangements follows. The asymmetric unit of the complex TMA·RSV·6.25H2O, namely two TMA molecules, two RSV

• longer axis of each macrocycle being approximately parallel to the planes of the respective included 4-hydroxyphenyl rings. In addition, the crystallographically independent TMA host molecules adopt somewhat different conformations given the fact that their contents differ, owing to the disorder

• )°], reflecting a more ‘closed’ primary side. Regarding the mode of guest inclusion, the angle between the mean plane of the RSV molecule and the mean O4-plane of the host molecule A is ca. 85.6°, with that between the RSV major disorder component B and the mean O4-plane of host molecule B being virtually the

Mono- and multilayers of molecular spoked carbazole wheels on graphite

• Stefan-S. Jester,
• A. Vikas Aggarwal,
• Daniel Kalle and
• Sigurd Höger

Beilstein J. Org. Chem. 2014, 10, 2783–2788, doi:10.3762/bjoc.10.295

• is fitted to match the MSW orientation (by rotation). The corners of adjacent hexagons are connected by solid black lines to form triangles and tetragons, the variation of the shapes of which points out the high degree of disorder. (f) The data obtained in (d) and (e) is translated into a

Encapsulation of biocides by cyclodextrins: toward synergistic effects against pathogens

• Véronique Nardello-Rataj and
• Loïc Leclercq

Beilstein J. Org. Chem. 2014, 10, 2603–2622, doi:10.3762/bjoc.10.273

• the modified ones reached the same level after 240 min because of the formation of inclusion complexes. However, the presence of β-CD and biocide increased the disorder of cellulose microstructure and modified its mechanical properties. The bacterial activity against E. coli and S. aureus exhibited

Molecular ordering at electrified interfaces: Template and potential effects

• Thanh Hai Phan and
• Klaus Wandelt

Beilstein J. Org. Chem. 2014, 10, 2243–2254, doi:10.3762/bjoc.10.233

• /P1’ and P3/P3’) [5][6][7][13][14][15][16], as well as to an order/disorder phase transition due to chloride desorption/adsorption [17]. As mentioned in the Introduction, the viologen dication (DBV2+) is known to undergo two successive one-electron transfer steps in the electrochemical environment