Nucleophilic dearomatization of 4-aza-6-nitrobenzofuroxan by CH acids in the synthesis of pharmacology-oriented compounds

• Alexey M. Starosotnikov,
• Dmitry V. Shkaev,
• Maxim A. Bastrakov,
• Ivan V. Fedyanin,
• Svyatoslav A. Shevelev and
• Igor L. Dalinger

Beilstein J. Org. Chem. 2017, 13, 2854–2861, doi:10.3762/bjoc.13.277

• drawn at 50% probability; a DMF molecule is omitted for clarity. Partial 1H NMR spectrum of compound 15 in DMSO-d6. General view of molecule 15 in crystal. Anisotropic displacement parameters for non-hydrogen atoms are drawn at 50% probability; a DMSO molecule and the minor component of the disordered

The use of 4,4,4-trifluorothreonine to stabilize extended peptide structures and mimic β-strands

• Yaochun Xu,
• Isabelle Correia,
• Tap Ha-Duong,
• Nadjib Kihal,
• Jean-Louis Soulier,
• Julia Kaffy,
• Benoît Crousse,
• Olivier Lequin and
• Sandrine Ongeri

Beilstein J. Org. Chem. 2017, 13, 2842–2853, doi:10.3762/bjoc.13.276

• the aforementioned extended conformations. More specifically, the probability of each residue to be in α- or β-conformation can be quantified by calculating the area under the peaks of the ψ distribution functions centered around −30° or +140°, respectively. The probability of the three central

• CSDs and 3JHN-Hα coupling constant values. The probability of each peptide to have all its three central residues in β-conformation (which is equal to the product of the three central residue probabilities) is a good indication of its propensity to adopt a global extended structure. According to this

• -protected pentapeptides 1a–4a and free amine pentapeptides 1b–4b. Probability distribution of the peptide conformations as a function of end-to-end distance (defined as the distance between the nitrogen of residue Ala1 and the carbon of the C-terminal carbonyl). Probability distribution of the peptide

Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes

• Takeshi Fujita,
• Ryo Kinoshita,
• Tsuyoshi Takanohashi,
• Naoto Suzuki and
• Junji Ichikawa

Beilstein J. Org. Chem. 2017, 13, 2682–2689, doi:10.3762/bjoc.13.266

• probability. ORTEP diagram of 6a with 50% ellipsoid probability. Intramolecular site-selective iodoarylation of 1,1-difluoro-1-alkenes bearing a biaryl group. Mechanism for formation of 3a. Transformation of a CF2I group of 2a into a CHF2 group. Construction of seven-membered carbocycles via iodoarylation of

A Brønsted base-promoted diastereoselective dimerization of azlactones

• Danielle L. J. Pinheiro,
• Gabriel M. F. Batista,
• Pedro P. de Castro,
• Leonã S. Flores,
• Gustavo F. S. Andrade and
• Giovanni W. Amarante

Beilstein J. Org. Chem. 2017, 13, 2663–2670, doi:10.3762/bjoc.13.264

• dimer. X-ray crystallographic structure of 2a (30% ellipsoids probability). Plausible mechanism for the dimerization of azlactone. Plot of vs time for the dimerization of azlactone 1a. X-ray crystallographic structure of 6 (30% ellipsoids probability). Diastereoselective dimerization of azlactones

Regioselective decarboxylative addition of malonic acid and its mono(thio)esters to 4-trifluoromethylpyrimidin-2(1H)-ones

• Sergii V. Melnykov,
• Andrii S. Pataman,
• Yurii V. Dmytriv,
• Svitlana V. Shishkina,
• Mykhailo V. Vovk and
• Volodymyr A. Sukach

Beilstein J. Org. Chem. 2017, 13, 2617–2625, doi:10.3762/bjoc.13.259

• heterochiral dimer in the crystal state. Intermolecular hydrogen bonds in the dimer are shown as dashed lines. Thermal ellipsoids are defined at 50% probability. Hydrogenation of compounds 4–6 and preparation of N1(3)-unsubstituted compounds 9–11d. Screening of the reaction conditions for organic base

Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes

• Jury J. Medvedev,
• Ilya V. Efimov,
• Yuri M. Shafran,
• Vitaliy V. Suslonov,
• Vasiliy A. Bakulev and
• Valerij A. Nikolaev

Beilstein J. Org. Chem. 2017, 13, 2569–2576, doi:10.3762/bjoc.13.253

• structure of thiophene 5c according to the data of X-ray analysis (Olex2 plot with 50% probability level of ellipsoids). The structure of the complex 6e according to the data of X-ray analysis (Olex2 plot with 50% probability level of ellipsoids). General scheme for intramolecular heterocylization of

Pyrene–nucleobase conjugates: synthesis, oligonucleotide binding and confocal bioimaging studies

• Artur Jabłoński,
• Yannic Fritz,
• Hans-Achim Wagenknecht,
• Rafał Czerwieniec,
• Tytus Bernaś,
• Damian Trzybiński,
• Krzysztof Woźniak and
• Konrad Kowalski

Beilstein J. Org. Chem. 2017, 13, 2521–2534, doi:10.3762/bjoc.13.249

• –nucleobase conjugates A1–A3. ORTEP diagram of 2 at 50% probability level. The hydrogen and halogen bonds are represented by dashed lines. Selected bond lengths (Å) and angles (°): O26–C17, 1.223(2); O27–C21, 1.233(2); O28–C23, 1.225(2); N20–C25, 1.380(2); N22–C21, 1.372(2); N22–C23, 1.389(2); C1–C17, 1.501(2

Synthesis and supramolecular properties of regioisomers of mononaphthylallyl derivatives of γ-cyclodextrin

• Markéta Bláhová,
• Sergey K. Filippov,
• Lubomír Kováčik,
• Jiří Horský,
• Simona Hybelbauerová,
• Zdenka Syrová,
• Tomáš Křížek and
• Jindřich Jindřich

Beilstein J. Org. Chem. 2017, 13, 2509–2520, doi:10.3762/bjoc.13.248

• consequently, longer oligomers can be expected for it. The fraction of suprapolymer with polymerization degree n is then given for negligible cyclisation as where θ is the degree of occupation, i.e., the probability that the particular group, either naphthyl or CD, is in a bound state. θ is determined by the

Syntheses, structures, and stabilities of aliphatic and aromatic fluorous iodine(I) and iodine(III) compounds: the role of iodine Lewis basicity

• Tathagata Mukherjee,
• Soumik Biswas,
• Andreas Ehnbom,
• Subrata K. Ghosh,
• Ibrahim El-Zoghbi,
• Nattamai Bhuvanesh,
• Hassan S. Bazzi and
• John A. Gladysz

Beilstein J. Org. Chem. 2017, 13, 2486–2501, doi:10.3762/bjoc.13.246

• para and ortho to the iodine atoms are denoted ° and ◊ (red = ArI; blue = ArICl2). Two views of the molecular structure of 1,3,5-(Rf6)2C6H3I with thermal ellipsoids at the 50% probability level. Key bond lengths (Å) and angles (°): C1–I1 2.099(3), C1–C2 1.391(4), C2–C3 1.386(4), C3–C4 1.393(4), C4–C5

Synthesis, effect of substituents on the regiochemistry and equilibrium studies of tetrazolo[1,5-a]pyrimidine/2-azidopyrimidines

• Elisandra Scapin,
• Paulo R. S. Salbego,
• Caroline R. Bender,
• Alexandre R. Meyer,
• Anderson B. Pagliari,
• Tainára Orlando,
• Geórgia C. Zimmer,
• Clarissa P. Frizzo,
• Helio G. Bonacorso,
• Nilo Zanatta and
• Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 2396–2407, doi:10.3762/bjoc.13.237

• (3JH-H) of (a) H6–H7 for 3a and (b) H5–H6 for 5h. LUMO coefficients for (a) β-enaminones 1a,h, and their (b) conjugated acids. (a) 1H and (b) 13C NMR spectra demonstrating the 3d4d equilibrium in DMSO-d6 at 25 °C. ORTEP® [45] plot of 7a with thermal ellipsoids drawn at 50% probability level. Tetrazolo

• [1,5-a]pyrimidine observed in solution (CDCl3 and DMSO-d6) and 2-azidopyrimidine observed in the solid state based on equilibrium. ORTEP® [45] plot of 8i with thermal ellipsoids drawn at 50% probability level. Representation of the possible equilibrium existing between 6i, 7i, and 8i. Reaction

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 atom-numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level. Only the major component of disordered fluorine atoms is presented. (b) Overlap of molecules 5–8 showing almost identical molecular conformation. Color code: 5 green, 6 orange, 7 purple, 8

One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P^® activation of 3-arylpropiolic acids

• Melanie Denißen,
• Alexander Kraus,
• Guido J. Reiss and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231

• and non-conjugated bichromophores in a rapid fashion. Studies directed towards the one-pot synthesis of more complex polycyclic emitters are currently underway. The ORTEP-style plot of crystal structure 4b (ellipsoids are draw at the 40% probability level). The ORTEP-type plot of the crystal structure

• 5 (left) and a centrosymmetric dimer formation by π–π interactions (right) (ellipsoids are drawn at the 40% probability level). The ORTEP-type plot of the asymmetric unit of the crystal structure 6 (top) and π-stacking interactions (bottom) (ellipsoids are drawn at the 40% probability level

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 heteroacenes. ORTEP drawing of compound 3 (left) and 4 (right) with 50% probability. All hydrogen atoms are omitted for clarity. One of two geometries in the unit cell was drawn for 4. UV–vis absorption (left) and normalized fluorescence emission (right, excitation at 335 nm) spectra in CH2Cl2

Regiodivergent condensation of 5-alkoxycarbonyl-1H-pyrrol-2,3-diones with cyclic ketazinones en route to spirocyclic scaffolds

• Alexey Yu. Dubovtsev,
• Maksim V. Dmitriev,
• Аndrey N. Maslivets and
• Michael Rubin

Beilstein J. Org. Chem. 2017, 13, 2179–2185, doi:10.3762/bjoc.13.218

• switched towards the formation of either of the products by tweaking steric parameters of the employed ketazinones. ORTEP drawing of compound 12ab (CCDC 1546062) showing 50% probability amplitude displacement ellipsoids. ORTEP drawing of compound 21ab (CCDC 1546063) showing 50% probability amplitude

• displacement ellipsoids. ORTEP drawing of compound 22a (CCDC 1546065) showing 50% probability amplitude displacement ellipsoids. ORTEP drawing of compound 23aa (CCDC 1546064) showing 50% probability amplitude displacement ellipsoids. Spirocyclization of enamines with 5-methoxycarbonyl-1H-pyrrolediones. Non

Mechanochemical enzymatic resolution of N-benzylated-β³-amino esters

• Mario Pérez-Venegas,
• Gloria Reyes-Rangel,
• Adrián Neri,
• Jaime Escalante and
• Eusebio Juaristi

Beilstein J. Org. Chem. 2017, 13, 1728–1734, doi:10.3762/bjoc.13.167

• affording the desired amino acids with good ee although with a decrease in conversion due to a partial denaturation process and partial destruction of the enzyme support. X-ray crystallographic structure of product (R)-2a (50% of probability ellipsoids). CCDC registry number 1552645. Enantioselective

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

• region at a given force, the remaining spectral lines were broadened using a Lorentzian with a full width at half maximum of 34 cm−1. To simulate spectra of polymer solids, the broadened spectra were convoluted with the probability distribution P(F) derived by Adhikari and Makarov [81], Equation 1, with

Chemical systems, chemical contiguity and the emergence of life

• Terrence P. Kee and
• Pierre-Alain Monnard

Beilstein J. Org. Chem. 2017, 13, 1551–1563, doi:10.3762/bjoc.13.155

• activity, the inserted PAH molecules in turn contributed to stabilizing the aggregates and reducing the bilayer permeability to additional small solutes [74]. That is, feedback interactions between system components significantly increase the probability of coupled functionality, in this case coupling of a

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

• opportunities for design of ICZ-cored molecules. ICZ-cored materials for organic electronic devices. General positions for SEAr in ICZs 1. X-ray single crystal structure of compound 2a. Thermal ellipsoids of 50% probability are presented. X-ray single crystal structure of compounds 9b and 10b. Thermal

• ellipsoids of 50% probability are presented. X-ray single crystal structure of compounds 12b and 13b. Thermal ellipsoids of 50% probability are presented. Double nitration of indolo[3,2-b]carbazole 1a. C2- and C2,8-nitration of indolo[3,2-b]carbazoles 1. Reduction of nitro-substituted ICZs 2 and 3. Nitration

From chemical metabolism to life: the origin of the genetic coding process

• Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

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

Metal-free hydroarylation of the side chain carbon–carbon double bond of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles in triflic acid

• Anna S. Zalivatskaya,
• Dmitry S. Ryabukhin,
• Marina V. Tarasenko,
• Alexander Yu. Ivanov,
• Irina A. Boyarskaya,
• Elena V. Grinenko,
• Ludmila V. Osetrova,
• Eugeniy R. Kofanov and
• Aleksander V. Vasilyev

Beilstein J. Org. Chem. 2017, 13, 883–894, doi:10.3762/bjoc.13.89

• ); ellipsoid contours of probability levels are 50%. The hydroarylation of 5-(2-arylethenyl)-3-aryl-1,2,4-oxadiazoles 1 under superelectrophilic activation leading to compounds 2. Selected electronic characteristics for cations A–F calculated by DFT from protonation of oxadiazole 1a. Hydroarylation of

Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

• Işıl Yenice,
• Sinan Basceken and
• Metin Balci

Beilstein J. Org. Chem. 2017, 13, 825–834, doi:10.3762/bjoc.13.83

• and methylene protons in 13c and 16 with the relevant carbon atoms (from the HMBC spectrum). Single-crystal X-ray structure of 12c shown with 40% probability displacement ellipsoids. The structure of allene 17 formed during the reaction of 7d with a base. Single-crystal X-ray structure of 19c shown

• with 40% probability displacement ellipsoids. Potential energy profile related to the formation of pyrrolooxazinone 19c in the polarizable continuum model (PCM) [34][35] with the hybrid functional M06 [36] using 6-31+G(d)/LANL2DZ level in dichloromethane. Distances are given in angstroms. (Relative

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

• ···O8 (1−x, 1−y, 1−z), O11–Ha 0.95 Å, O11···O8 2.979(3) Å, Ha···O8 2.05 Å, <(O11–Ha···O8) 169°. Solid-state structure of mesoionic compound 7a (ORTEP plot); thermal displacement ellipsoids are drawn at the 30% probability level. Selected bond lengths (Å): C1–N1 1.343(1), C1–N3 1.398(1), C1–N5 1.322(1

Regiochemistry of cyclocondensation reactions in the synthesis of polyazaheterocycles

• Patrick T. Campos,
• Leticia V. Rodrigues,
• Andrei L. Belladona,
• Caroline R. Bender,
• Juliana S. Bitencurt,
• Fernanda A. Rosa,
• Davi F. Back,
• Helio G. Bonacorso,
• Nilo Zanatta,
• Clarissa P. Frizzo and
• Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 257–266, doi:10.3762/bjoc.13.29

• are thermodynamically controlled. The proposed reaction mechanism, which is based on DFT-B3LYP data, demonstrates that an intermediate amide is expected, rather than an imine amide. ORTEP plot of 6, 9c, and 12g with the thermal ellipsoids drawn at the following probability levels: (a) 20%, (b) 50

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

• (50 mL), the resulted solution was concentrated under vacuum and the desired biaryl was isolated by column chromatography. The steric geometry-constrained iminopyridyl–palladium complexes. ORTEP drawing of Pd2 with thermal ellipsoids at 30% probability level. Hydrogen atoms and the solvent CH2Cl2 have