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

• . 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

Synthesis of spiro[isoindole-1,5’-isoxazolidin]-3(2H)-ones as potential inhibitors of the MDM2-p53 interaction

• Salvatore V. Giofrè,
• Santa Cirmi,
• Raffaella Mancuso,
• Francesco Nicolò,
• Giuseppe Lanza,
• Laura Legnani,
• Agata Campisi,
• Maria A. Chiacchio,
• Michele Navarra,
• Bartolo Gabriele and
• Roberto Romeo

Beilstein J. Org. Chem. 2016, 12, 2793–2807, doi:10.3762/bjoc.12.278

• ’, respectively). Crystal packing is a racemate due to the centrosymmetric symmetry and in the picture the choice of the enantiomer is arbitrary. C: light blue, H: white, O: red, N: magenta. Probability of the ORTEP ellipsoids is set to 50%, whereas H size is arbitrary. Three-dimensional plots of TSs of reaction

Computational methods in drug discovery

• Sumudu P. Leelananda and
• Steffen Lindert

Beilstein J. Org. Chem. 2016, 12, 2694–2718, doi:10.3762/bjoc.12.267

• bringing a drug to the market has increased nearly 150% in the last decade. The cost is now estimated to be a staggering $2.6 billion dollars. The probability of a failure in the drug discovery and development pipeline is high and 90% of the drugs entering clinical trials fail to get FDA approval and reach

• target molecule is simulated in an aqueous solution that contains different fragments. Using multiple simulations SILCS determines high probability binding areas of the target for the different fragments which can be used in fragment-based drug design. Another de novo ligand design program is LigBuilder

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

• carbenes. Molecular drawing of one of the two crystallographic independent molecules of borane adduct 8 (displacement parameters are drawn at 50% probability level; crystallographic numbering). Molecular drawing of the cation of the gold complex 9 (displacement parameters are drawn at 50% probability level

• ; 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

Thiazol-4-one derivatives from the reaction of monosubstituted thioureas with maleimides: structures and factors determining the selectivity and tautomeric equilibrium in solution

• Alena S. Pankova,
• Pavel R. Golubev,
• Alexander F. Khlebnikov,
• Alexander Yu. Ivanov and
• Mikhail A. Kuznetsov

Beilstein J. Org. Chem. 2016, 12, 2563–2569, doi:10.3762/bjoc.12.251

• can be used for the targeted synthesis of various aminothiazolidinones. OLEX2 representation of the crystal structure of thiazolidine 3b. Thermal ellipsoids are given at the 50% probability level. Fragments of the 1H NMR spectra of thiazolidine 3g at −20 °C (1), 23 °C (2) and 120 °C (3). Spectrum (1

Sydnone C-4 heteroarylation with an indolizine ring via Chichibabin indolizine synthesis

• Florin Albota,
• Mino R. Caira,
• Constantin Draghici,
• Florea Dumitrascu and
• Denisa E. Dumitrescu

Beilstein J. Org. Chem. 2016, 12, 2503–2510, doi:10.3762/bjoc.12.245

• significant intramolecular distortion in the other. Sydnone-pyrroloazines hybrids 1, indolizine (2), sydnone 3, indolizines attached directly to C-4 of a sydnone 4, indolizines attached via a keto group to C-4 of a sydnone 5. The molecular structure of 9d with thermal ellipsoids drawn at the 50% probability

• ), C4–C5 1.414(2), C5–O1 1.402(2), and C5–O6 1.222(2). Centrosymmetric C–H···O hydrogen bonded dimeric motif in the crystal of 9d. Molecular structure of 12c with atoms represented as thermal ellipsoids at the 50% probability level. Dotted lines indicate intramolecular hydrogen bonds. Bond distances (Å

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

• Constantin Mamat,
• Marc Pretze,
• Matthew Gott and
• Martin Köckerling

Beilstein J. Org. Chem. 2016, 12, 2478–2489, doi:10.3762/bjoc.12.242

• ). Molecular structure of compound 3a (ORTEP plot with 50% probability level). Molecular structure of compound 4b (ORTEP plot with 50% probability level). Superimposition fit of the two conformers, which exist in the ratio of 1:1 in the solid state structure of compound 4b (label A marks the atoms of the

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

• Artem N. Semakin,
• Aleksandr O. Kokuev,
• Yulia V. Nelyubina,
• Alexey Yu. Sukhorukov,
• Petr A. Zhmurov,
• Sema L. Ioffe and
• Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

• amine, 3.1 equiv of 1a, 3 equiv of K2CO3; D. 1 equiv of amine, 4.2 equiv of 1a, 4 equiv of K2CO3. Yield based on the amine used. General view of 13b in representation of atoms with thermal ellipsoids at 50% probability level; all hydrogen atoms (except for those of the NH groups) are omitted for clarity

A direct method for the N-tetraalkylation of azamacrocycles

• Andrew J. Counsell,
• Angus T. Jones,
• Matthew H. Todd and
• Peter J. Rutledge

Beilstein J. Org. Chem. 2016, 12, 2457–2461, doi:10.3762/bjoc.12.239

• ] and POV-Ray [52]. Ellipsoids shown at 50% probability. The asymmetric unit consists of one half of the ligand and one perchlorate anion. N-Tetraalkylation of cyclam (1) and cyclen (2) with alkyl halides in partially miscible aqueous–organic biphasic systems. Reagents and conditions: H2O/CH3CN (1:1

A new paradigm for designing ring construction strategies for green organic synthesis: implications for the discovery of multicomponent reactions to build molecules containing a single ring

• John Andraos

Beilstein J. Org. Chem. 2016, 12, 2420–2442, doi:10.3762/bjoc.12.236

• economy; green organic synthesis; integer partitioning; reactions; probability; retrosynthetic analysis; ring construction strategy; Introduction The ring motif is a key feature in chemical structures that has long attracted the attention of synthetic organic chemists in their quest to implement novel

• starting materials to the final desired products. Recently, a measure of the associated probability of achieving reaction intrinsic “greenness” based on simple reaction yield (RY) and atom economy (AE) threshold constraints was advanced [9]. That work demonstrated that both of these metrics, which define

• that AE(min) > 60% and RY > 80%. Additionally, since the experimental reaction yield quantity is fractional, the analysis interpreted it as a probability of reaction occurrence to a given product given a set of reaction conditions and starting materials. Reaction outcomes with high yields mean that the

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

• chlorides 2. Imidazolylisoxazole 4a according to XRD data in the thermal ellipsoids of the 50% probability level. Isoxazolylisoxazole 4p according to XRD data with thermal ellipsoids of 50% probability level. Geometries of enamine 1a appropriate to the calculated minima on the PES, and their relative free

Robust C–C bonded porous networks with chemically designed functionalities for improved CO₂ capture from flue gas

• Damien Thirion,
• Joo S. Lee,
• Ercan Özdemir and
• Cafer T. Yavuz

Beilstein J. Org. Chem. 2016, 12, 2274–2279, doi:10.3762/bjoc.12.220

• kJ mol−1 (Table 1, Figure 2 and Supporting Information File 1, Figure S3). COP-157 gave a similar isotherm but with lesser surface area (Supporting Information File 1, Figures S4 and S5). This could be explained by a higher interpenetration probability of the network structure than in COP-156, as the

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

• Alexei N. Izmest’ev,
• Galina A. Gazieva,
• Natalya V. Sigay,
• Sergei A. Serkov,
• Valentina A. Karnoukhova,
• Vadim V. Kachala,
• Alexander S. Shashkov,
• Igor E. Zanin,
• Angelina N. Kravchenko and
• Nina N. Makhova

Beilstein J. Org. Chem. 2016, 12, 2240–2249, doi:10.3762/bjoc.12.216

• ), isatins 3 (0.5 mmol), and sarcosine (0.5 mmol) in the mixture of acetonitrile (30 mL) and chloroform (10 mL) for 72 h. Key interactions in {1H-13C}HMBC spectrum of 4f. General view of 4c in the crystal in thermal ellipsoids representation (50% probability). Hydrogen atoms connected to carbon atoms are

• omitted for clarity. General view of 4e in the crystal in thermal ellipsoids representation (40% probability). Hydrogen atoms connected to carbon atoms are omitted for clarity. General view of 4r in the crystal in thermal ellipsoids representation (50% probability). Hydrogen atoms connected to carbon

Superelectrophilic activation of 5-hydroxymethylfurfural and 2,5-diformylfuran: organic synthesis based on biomass-derived products

• Dmitry S. Ryabukhin,
• Dmitry N. Zakusilo,
• Mikhail O. Kompanets,
• Anton A.Tarakanov,
• Irina A. Boyarskaya,
• Tatiana O. Artamonova,
• Mikhail A. Khohodorkovskiy,
• Iosyp O. Opeida and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2016, 12, 2125–2135, doi:10.3762/bjoc.12.202

• -glucose or D-fructose followed by oxidation to 2,5-DFF. X-ray crystal structure of compounds 5a (a), and 5c (b) (ORTEP diagrams, ellipsoid contour of probability levels is 50%, CCDC reference numbers 5a: 1483523, 5c: 1483524). Protonation of 5-HMF (1a) and 2,5-DFF (2) leading to cationic species A, B, C

Chiral ammonium betaine-catalyzed asymmetric Mannich-type reaction of oxindoles

• Masahiro Torii,
• Kohsuke Kato,
• Daisuke Uraguchi and
• Takashi Ooi

Beilstein J. Org. Chem. 2016, 12, 2099–2103, doi:10.3762/bjoc.12.199

• (Ellipsoids displayed at 50% probability. Calculated hydrogen atoms except it attaches to stereogenic carbon are omitted for clarity. Black: carbon, Red: oxygen, Blue: nitrogen, Green: chlorine). Optimization of catalyst structure.a Substrate scope.a Supporting Information Supporting Information File 379

Diastereoselective synthesis of 3,4-dihydro-2H-pyran-4-carboxamides through an unusual regiospecific quasi-hydrolysis of a cyano group

• Mikhail Yu. Ievlev,
• Oleg V. Ershov,
• Mikhail Yu. Belikov,
• Angelina G. Milovidova,
• Viktor A. Tafeenko and
• Oleg E. Nasakin

Beilstein J. Org. Chem. 2016, 12, 2093–2098, doi:10.3762/bjoc.12.198

• biological studies. The molecular structure of 2a with atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are drawn as small spheres of arbitrary radii. An exclusive approach to 3,4-dihydro-2H-pyran-4-carboxamides from non-pyran sources. Known approach to pyran

Synthesis and characterization of fluorinated azadipyrromethene complexes as acceptors for organic photovoltaics

• Forrest S. Etheridge,
• Roshan J. Fernando,
• Sandra Pejić,
• Matthias Zeller and
• Geneviève Sauvé

Beilstein J. Org. Chem. 2016, 12, 1925–1938, doi:10.3762/bjoc.12.182

• cyclic voltammetry from the E1/2 values in dichloromethane solution, using the value of −5.1 eV for Fc/Fc+. The included HOMO and LUMO levels of P3HT films were estimated in our laboratory from the oxidation onset and the optical gap. ORTEP drawing of Zn(L2)2 with ellipsoids drawn at the 50% probability

• level and a partial labeling scheme. The hydrogen atoms, and dichloromethane solvate were omitted for clarity. ORTEP drawing of Zn(L2)2 with ellipsoids drawn at the 50% probability level and a partial labeling scheme. The hydrogen atoms, and dichloromethane solvate were omitted for clarity. a) Shows the

Bridgehead vicinal diallylation of norbornene derivatives and extension to propellane derivatives via ring-closing metathesis

• Sambasivarao Kotha and
• Rama Gunta

Beilstein J. Org. Chem. 2016, 12, 1877–1883, doi:10.3762/bjoc.12.177

• allyl groups and oxa-bowl/propellane hybrids. Since non-flattened molecules are implicated in biological systems, our results would be useful in drug design [42]. Retrosynthetic approach to propellane derivatives. The molecular structure of 1a, with displacement ellipsoids drawn at the 50% probability

Experimental and theoretical insights in the alkene–arene intramolecular π-stacking interaction

• Valeria Corne,
• Ariel M. Sarotti,
• Carmen Ramirez de Arellano,
• Rolando A. Spanevello and
• Alejandra G. Suárez

Beilstein J. Org. Chem. 2016, 12, 1616–1623, doi:10.3762/bjoc.12.158

• (in kcal/mol) computed for 6d and 6b (in grey). X-ray thermal ellipsoid plot of 6a (50% probability level) showing the labeling scheme (hydrogen and carbon labels have been omitted for clarity). Synthesis of acrylates 6a,b. Complexes between methyl acrylate (7) and representative anisole derivatives

A T-shape diphosphinoborane palladium(0) complex

• Patrick Steinhoff and
• Michael E. Tauchert

Beilstein J. Org. Chem. 2016, 12, 1573–1576, doi:10.3762/bjoc.12.152

• chelating diphosphine ligand by introduction of a borane acceptor functionality. Selected M→B coordination modes 1–5 [6][7][8][9][10] and Hofmann’s Rucaphos complex 6 [11]. Thermal ellipsoid plots of complex 9 at the 50% probability level. H atoms and one molecule of hexane have been omitted for clarity

Methylpalladium complexes with pyrimidine-functionalized N-heterocyclic carbene ligands

• Dirk Meyer and
• Thomas Strassner

Beilstein J. Org. Chem. 2016, 12, 1557–1565, doi:10.3762/bjoc.12.150

• ]. Possible isomers. ORTEP [39] style plot of complex 9 in the solid state. Thermal ellipsoids are given at the 50% probability level. Selected bond lengths in angstrom and angles in degrees: Pd–C1 2.031(4), Pd–N3 2.137(2), Pd–C12 2.030(2), Pd–Cl1 2.342(1), C1–Pd–N3 80.1(1), C1–N1–C4–N3 −9.7(3). ORTEP [39

• ] style plot of complex 12 in the solid state. Thermal ellipsoids are drawn at the 50% probability level. Selected bond lengths in angstrom and angles in degrees: Pd–C1 1.966(4), Pd–N3 2.145(3), Pd–C14 2.035(3), Pd–Cl1 2.341(1), C1–Pd–N3 79.0(1), C1–N1–C4–N3 −5.9(5). ORTEP [39] style plot of complex 13 in

• the solid state. Thermal ellipsoids are drawn at the 50% probability level. Selected bond lengths in angstrom and angles in degrees: Pd–C1 1.956(2), Pd–N3 2.151(2), Pd–C20 2.015(2), Pd–O1 2.098(2), C1–Pd–N3 79.6(1), C1–N1–C4–N3 −3.3(3). Synthesis of the monomethylpalladium(II) complexes 9–11 (in DCM

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

Molecular weight control in organochromium olefin polymerization catalysis by hemilabile ligand–metal interactions

• Stefan Mark,
• Hubert Wadepohl and
• Markus Enders

Beilstein J. Org. Chem. 2016, 12, 1372–1379, doi:10.3762/bjoc.12.131

• produce without lowering their very high catalytic activity. Solid-state molecular structures of selected complexes 4, 7 and 8 (left, middle and right, respectively). Probability level: 50%. Hydrogen atoms and carbon labels are omitted for clarity. a) Calculated structures of cationic chromium complexes

Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides

• Mizuki Yamada,
• Mio Matsumura,
• Yuki Uchida,
• Masatoshi Kawahata,
• Yuki Murata,
• Naoki Kakusawa,
• Kentaro Yamaguchi and
• Shuji Yasuike

Beilstein J. Org. Chem. 2016, 12, 1309–1313, doi:10.3762/bjoc.12.123

• ammonia and water, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane:AcOEt) to give 3b, 3i (8:1), 3f (6:1), 3g, 3h (5:1), 3c, 3d, 3e, 3j (4:1), 3k (1:1). Ortep drawing of 3a with 50% probability. All hydrogen atoms are omitted for

Stereoselective synthesis of tricyclic compounds by intramolecular palladium-catalyzed addition of aryl iodides to carbonyl groups

• Jakub Saadi,
• Christoph Bentz,
• Kai Redies,
• Dieter Lentz,
• Reinhold Zimmer and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2016, 12, 1236–1242, doi:10.3762/bjoc.12.118

• the discovered aryl iodide addition to carbonyl groups may be limited it is attractive since only low catalyst loadings are required and interesting products are formed with high stereoselectivity. Molecular structure (ORTEP, [14]) of compound 12a (thermal ellipsoids at 50% probability). Molecular

• structure (ORTEP, [14]) of compound 14a (thermal ellipsoids at 50% probability). Molecular structure (ORTEP, [14]) of compound 15a (thermal ellipsoids at 50% probability). Molecular structure (ORTEP [14]) of compound 15b (thermal ellipsoids at 50% probability). Planned Heck reaction of A to compound B and