Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• the reaction was not complete. ESR spectra of samples obtained after milling by methods 2a (black), 2b (red) and 2c (blue). The inset shows the spectrum of [Cu(OAc)2(H2O)]2 [53]. All spectra are recorded at room temperature. X-ray structure of the triazole compounds. (a) Molecular structure of 5, with

Synthesis and photophysical properties of novel benzophospholo[3,2-b]indole derivatives

• Mio Matsumura,
• Mizuki Yamada,
• Atsuya Muranaka,
• Misae Kanai,
• Naoki Kakusawa,
• Daisuke Hashizume,
• Masanobu Uchiyama and
• Shuji Yasuike

Beilstein J. Org. Chem. 2017, 13, 2304–2309, doi:10.3762/bjoc.13.226

• tetracyclic moieties are planar. The benzophosphole-fused indoles, such as phosphine oxide, phospholium salt, and borane complex, exhibited strong photoluminescence in dichloromethane (Φ = 67–75%). Keywords: benzophospholo[3,2-b]indole; DFT calculation; molecular structure; phosphole derivatives

• -fused benzoheteroles containing the group 15 and 16 elements using the ring-closing reaction of dilithium compounds with electrophiles bearing heteroatoms [36]. In continuation of our research, we were interested in the synthesis, molecular structure, and physicochemical properties of the parent

Synthesis and application of trifluoroethoxy-substituted phthalocyanines and subphthalocyanines

• Satoru Mori and
• Norio Shibata

Beilstein J. Org. Chem. 2017, 13, 2273–2296, doi:10.3762/bjoc.13.224

• 14 exhibited aggregation behavior by an intramolecular stacking interaction between the units (Figure 5). On the other hand, the trifluoroethoxy-substituted trimer 13 did not exhibit such aggregation behavior and adopted a “windmill-like molecular structure” by the repulsive action of the

• spectra of 9 (A) and 5 (B). Structure of binuclear phthalocyanines linked by a triazole linker. Structure of trinuclear phthalocyanines linked by a triazole linker, and windmill-like molecular structure vs aggregated structure. Direction of energy transfer of phthalocyanine–fullerene conjugates. Structure

Structural diversity in the host–guest complexes of the antifolate pemetrexed with native cyclodextrins: gas phase, solution and solid state studies

• Magdalena Ceborska,
• Magdalena Zimnicka,
• Aneta Aniela Kowalska,
• Kajetan Dąbrowa and
• Barbara Repeć

Beilstein J. Org. Chem. 2017, 13, 2252–2263, doi:10.3762/bjoc.13.222

• still presents a challenge for medicinal and pharmaceutical studies, involving the search for new molecules acting as folate inhibitors [11][12], as well as their recognition mechanisms [13][14]. The molecular structure of PTX closely resembles folic acid (FA, Figure 1a), and hence, it belongs to the

The effect of milling frequency on a mechanochemical organic reaction monitored by in situ Raman spectroscopy

• Patrick A. Julien,
• Ivani Malvestiti and
• Tomislav Friščić

Beilstein J. Org. Chem. 2017, 13, 2160–2168, doi:10.3762/bjoc.13.216

• molecular structure rather than its crystallinity, offering a powerful tool for in situ studies of mechanochemical organic reactions that often proceed through amorphous or eutectic intermediates. We now report a Raman spectroscopy study of the effect of ball milling frequency on the course of a model

Mechanochemical synthesis of thioureas, ureas and guanidines

• Vjekoslav Štrukil

Beilstein J. Org. Chem. 2017, 13, 1828–1849, doi:10.3762/bjoc.13.178

• -thiourea 21a with 4-chloro- and 4-nitrophenyl isothiocyanates. This study demonstrated that solid-state ball milling can efficiently be employed for desymmetrization of ortho- and para-phenylenediamines, enabling selective functionalization of small symmetrical molecules through the extension of molecular

• structure in a one-pot two-step mechanochemical sequence. Another typical synthetic method for the preparation of thioureas, particularly if the desired isothiocyanate is not available, is the condensation of an amine with carbon disulfide [36]. This reaction proceeds through the formation of a

Theoretical simulation of the infrared signature of mechanically stressed polymer solids

• Matthew S. Sammon,
• Milan Ončák and
• Martin K. Beyer

Beilstein J. Org. Chem. 2017, 13, 1710–1716, doi:10.3762/bjoc.13.165

• in stress-induced aging of polymeric materials [1][10]. On the other hand, elegant routes have been established to harness this effect for the design of self-healing and stress-responsive materials [11][12][13][14][15]. The influence of an external force on the molecular structure of a polymer can be

Grip on complexity in chemical reaction networks

• Albert S. Y. Wong and
• Wilhelm T. S. Huck

Beilstein J. Org. Chem. 2017, 13, 1486–1497, doi:10.3762/bjoc.13.147

• true when those changes induce systems beyond a critical value, where the resulting abrupt shifts or phase transitions become unpredictable [20][21][22]. The analysis of the structure and the dynamics of a complex web of intricate interactions is a risk in removing the link between molecular structure

• borrowing principles from chemical engineering [37]. Isolating the influence of molecular structure on network function and dynamics will reveal the rules governing CRNs, as well as the complexity in systems like the cell. Minimal chemical reaction networks Network motifs assembled from feedback loops Much

• oscillation periods enable the construction of more complex systems capable of dynamical self-assembly. In this case, it is a dynamic self-assembly that is exactly out-of-phase with the initial oscillations. Correlating the molecular structure to network behavior This design strategy enables the chemist to

Nitration of 5,11-dihydroindolo[3,2-b]carbazoles and synthetic applications of their nitro-substituted derivatives

• Roman A. Irgashev,
• Nikita A. Kazin,
• Gennady L. Rusinov and
• Valery N. Charushin

Beilstein J. Org. Chem. 2017, 13, 1396–1406, doi:10.3762/bjoc.13.136

• desired product in 88% yield. At the same time, in the experiment with fuming nitric acid (5 equiv), used instead of acetyl nitrate (Table 1, entry 5), we have obtained a mixture of compound 2a and byproducts again. The molecular structure of compound 2a has been proved unequivocally by X-ray

Detection of therapeutic radiation in three-dimensions

• John A. Adamovics

Beilstein J. Org. Chem. 2017, 13, 1325–1331, doi:10.3762/bjoc.13.129

• quantified spectrophotometrically. In order to stabilize the geometric dose information in the Fricke solution aqueous based gel matrices containing the chelator xylenol orange were reported [9][10][11] with the molecular structure shown in Figure 1. When analyzed spectrophotometrically, a non-irradiated

Towards open-ended evolution in self-replicating molecular systems

• Herman Duim and
• Sijbren Otto

Beilstein J. Org. Chem. 2017, 13, 1189–1203, doi:10.3762/bjoc.13.118

• information only appeared later. These self-replicating molecules carry hereditary information in the form of their molecular structure that can be passed on to successive generations. If mutations occur during the replication process, genetic information can change from one generation to the next. Natural

• transfer of information in replicating molecules may be less obvious, but if one considers a polymer with a specific sequence of subunits, it is clear that some form of genetic information is transferred if the copies have an identical sequence to the parent molecule. The survival of a particular molecular

• structure under a set of environmental conditions depends on both the rate of replication and the rate of decomposition of this replicator. If a replicator decomposes at a higher rate than that it is produced, that particular replicator may become extinct. If, on the other hand, the sequence and structure

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• procedure in direct space to locate the molecule in the unit cell. Once the carbohydrate backbone was positioned, the refinement continued by an adjustment of the rotations of the glycosidic linkages and side chains. The final construction and model completion provided the crystal and molecular structure

New tricks of well-known aminoazoles in isocyanide-based multicomponent reactions and antibacterial activity of the compounds synthesized

• Maryna V. Murlykina,
• Maryna N. Kornet,
• Sergey M. Desenko,
• Svetlana V. Shishkina,
• Oleg V. Shishkin,
• Aleksander A. Brazhko,
• Vladimir I. Musatov,
• Erik V. Van der Eycken and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2017, 13, 1050–1063, doi:10.3762/bjoc.13.104

• compounds 4 and 6. Selected data of HSQC and HMBC experiments for compound 4a. Molecular structure of 3-(tert-butylamino)-2-(4-chlorophenyl)-N-(4-fluorophenyl)-1H-imidazo[1,2-b]pyrazole-7-carboxamide (4e) (X-ray diffraction data). Non-hydrogen atoms are presented as thermal ellipsoids with 50% probability

• . Selected data of NOE and HSQC experiments for compound 9d. Molecular structure of N-(2-(tert-butylamino)-1-(4-chlorophenyl)-2-oxoethyl)-N-(5-methylisoxazol-3-yl)-3-phenylpropiolamide (9e) (X-ray diffraction data). Non-hydrogen atoms are presented as thermal ellipsoids with 50% probability. Aminoazoles in

Regioselective (thio)carbamoylation of 2,7-di-tert-butylpyrene at the 1-position with iso(thio)cyanates

• Anna Wrona-Piotrowicz,
• Marzena Witalewska,
• Janusz Zakrzewski and
• Anna Makal

Beilstein J. Org. Chem. 2017, 13, 1032–1038, doi:10.3762/bjoc.13.102

• , 7.98; O, 4.48; found: C, 87.57; H, 8.05. Sites of electrophilic attack in 1 and 2. Molecular structure of 4. Triflic acid promoted reaction of 2 with iso(thio)cyanates. Triflic acid promoted reaction of 2 with ethoxycarbonyl isothiocyanate. Friedel–Crafts acylation of 2. Reaction of 2 with

Molecular-level architectural design using benzothiadiazole-based polymers for photovoltaic applications

• Vinila N. Viswanathan,
• Arun D. Rao,
• Upendra K. Pandey,
• Arul Varman Kesavan and
• Praveen C. Ramamurthy

Beilstein J. Org. Chem. 2017, 13, 863–873, doi:10.3762/bjoc.13.87

• significant role in increasing the efficiency for OPVs [30][31]. However, fused π-bridges (such as thienothiophene) having a larger molecular structure and higher degree of conjugation are less explored with respect to thiophene and furan spacers. Thienothiophene ensures a highly delocalized electron system

Continuous-flow processes for the catalytic partial hydrogenation reaction of alkynes

• Carmen Moreno-Marrodan,
• Francesca Liguori and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2017, 13, 734–754, doi:10.3762/bjoc.13.73

• scope An explanation for efficiency differences observed in catalytic flow reactors in relation to the molecular structure and/or substituent groups of alkynes substrates is not apparent due to a number of reasons. For example, although a higher selectivity in partial hydrogenation was reported for 1

Membrane properties of hydroxycholesterols related to the brain cholesterol metabolism

• Malte Hilsch,
• Ivan Haralampiev,
• Peter Müller,
• Daniel Huster and
• Holger A. Scheidt

Beilstein J. Org. Chem. 2017, 13, 720–727, doi:10.3762/bjoc.13.71

• constituents, resulting in highly characteristic effects on the packing and lateral organization of the membrane lipids and proteins [1][10][11][12][13]. Even very small alterations in the molecular structure of cholesterol cause large differences in the interaction with phospholipids and its membrane’s

Derivatives of the triaminoguanidinium ion, 5. Acylation of triaminoguanidines leading to symmetrical tris(acylamino)guanidines and mesoionic 1,2,4-triazolium-3-aminides

• Jan Szabo,
• Julian Greiner and
• Gerhard Maas

Beilstein J. Org. Chem. 2017, 13, 579–588, doi:10.3762/bjoc.13.57

• with respect to their structural and electronic properties, we herein present some relevant data of the 1,2,4-triazolium-hydrazinides 7. Thus, the molecular structure of 7a in the solid state was determined by X-ray diffraction analysis and is shown in Figure 4. Two symmetrically independent molecules

• chemistry. Molecular structure of 6b·2C2H5OH in the solid state, with numbering of atoms (ORTEP plot). Selected bond lengths (Å): C1–N1 1.297(4), C1–C2 1.390(4), C1–N3 1.365(4). Selected bond angles (°): N1–C1–N2 117.3(3), N2–C1–N3 115.6(2), N1–C1–N3 126.9(3). Hydrogen bonds to the two ethanol molecules: N2

• –H···O13: N2···O13 3.060(1) Å, NH···O13 1.96(2) Å; N3–H···O14(1.5−x, y−0.5, 0.5−z): N3···O14 2.917(4) Å, NH···O14 2.11(2) Å; O13–H···O5(−x+1, -y, −z+1): O13···O5 2.733(3) Å, (O13–)H···O5 1.97 Å; O14–H···O1: O14···O1 2.846(4) Å, (O14–)H···O1 2.07(6) Å. Left: molecular structure of 8b in the solid

Adsorption of RNA on mineral surfaces and mineral precipitates

• Elisa Biondi,
• Yoshihiro Furukawa,
• Jun Kawai and
• Steven A. Benner

Beilstein J. Org. Chem. 2017, 13, 393–404, doi:10.3762/bjoc.13.42

• more than either resembles calcite. Together, these results suggest, at least at the level of hypothesis, that the molecular structure of RNA is more compatible with the surface of an orthorhombic carbonate crystal (the “aragonite group”) having cations arranged with pseudo-hexagonal symmetry, than

Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties

• Maximilian Maier,
• Magnus S. Schmidt,
• Markus Ringwald and
• Christoph P. Fik

Beilstein J. Org. Chem. 2017, 13, 372–383, doi:10.3762/bjoc.13.40

• , connecting two N-allylacrylamide groups, thus adding a two-way, intramolecular reaction site. In order to individually assess the effect of “internal” and “external” (at the molecules’ periphery) N-allylic functions on the physical/polymerization properties, a systematic variation of the molecular structure

Highly bulky and stable geometry-constrained iminopyridines: Synthesis, structure and application in Pd-catalyzed Suzuki coupling of aryl chlorides

• Yi Lai,
• Zhijian Zong,
• Yujie Tang,
• Weimin Mo,
• Nan Sun,
• Baoxiang Hu,
• Zhenlu Shen,
• Liqun Jin,
• Wen-hua Sun and
• Xinquan Hu

Beilstein J. Org. Chem. 2017, 13, 213–221, doi:10.3762/bjoc.13.24

• by slow diffusion of diethyl ether to a saturated dichloromethane solution and the molecular structure in solid state was determined by X-ray diffraction [73]. Presented in Figure 2, the molecular structure and the predicted conformation was unambiguously confirmed. The same as before, the complexes

Dynamics and interactions of ibuprofen in cyclodextrin nanosponges by solid-state NMR spectroscopy

• Monica Ferro,
• Franca Castiglione,
• Nadia Pastori,
• Carlo Punta,
• Lucio Melone,
• Walter Panzeri,
• Barbara Rossi,
• Francesco Trotta and
• Andrea Mele

Beilstein J. Org. Chem. 2017, 13, 182–194, doi:10.3762/bjoc.13.21

• ) pure IbuNa (reference spectrum). The molecular structure and atom numbering of IbuNa are shown in the inset. The notation CDNS-IbuNa indicates the original preparation, irrespective of the conversion of the sodium salt into the undissociated acid. 13C CP-MAS NMR spectra of CDNS(1:4) acquired with CP

A new class of organogelators based on triphenylmethyl derivatives of primary alcohols: hydrophobic interactions alone can mediate gelation

• Wangkhem P. Singh and
• Rajkumar S. Singh

Beilstein J. Org. Chem. 2017, 13, 138–149, doi:10.3762/bjoc.13.17

• coordination, ionic, hydrophobic forces, etc.) into the gelator molecular structure and studying their gelation behaviour. H-bonding interaction (present in amide, urea, carbamate linkages, etc) alone or in combination with other interactions is the most extensively used strategy in the design of gelators [23

cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

• Dimpee Gogoi,
• Runjun Devi,
• Pallab Pahari,
• Bipul Sarma and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2016, 12, 2816–2822, doi:10.3762/bjoc.12.280

• evidences for the structural assignment were sought from X-ray crystallography. Fortunately, we got the single crystals of (±)-5k by slow evaporation of a solution of 5k in hexane/EtOAc, and its molecular structure was confirmed by X-ray diffraction analysis (Figure 3). The 1H and 13C NMR spectra of all the

Characterization of the synthetic cannabinoid MDMB-CHMCZCA

• Carina Weber,
• Stefan Pusch,
• Dieter Schollmeyer,
• Sascha Münster-Müller,
• Michael Pütz and
• Till Opatz

Beilstein J. Org. Chem. 2016, 12, 2808–2815, doi:10.3762/bjoc.12.279

• Chiralpak IA-3 column (length: 25 cm, diameter: 4.6 mm, particle size: 3 μm; Daicel) was used at a temperature of 40 °C. Synthetic cannabinoids JWH-018 (1), MDMB-CHMICA (2), MDMB-CHMCZCA (3), and EG-018 (4). Molecular structure of (S)-MDMB-CHMCZCA (3) with numbering scheme. ESI-MSn pattern of 3 (m/z values

• . Molecular structure of (S)-3 in the solid state at 110 K (ORTEP-ellipsoids drawn at 30% probability, C black, H gray, N blue, O red). UV traces (254 nm) of the chiral HPLC for commercial (S)-3 (top) and the (R/S)-3 (bottom). tR = 6.84 min (R) and 7.93 min (S). Enantiomeric excesses of (S)-3 as determined by