Reversible photoswitching of the DNA-binding properties of styrylquinolizinium derivatives through photochromic [2 + 2] cycloaddition and cycloreversion

• Sarah Kölsch,
• Heiko Ihmels,
• Jochen Mattay,
• Norbert Sewald and
• Brian O. Patrick

Beilstein J. Org. Chem. 2020, 16, 111–124, doi:10.3762/bjoc.16.13

• single crystals after slow evaporation, their structure was determined by single crystal X-ray diffraction (XRD) analysis (Figure 8, cf. Supporting Information File 1). The cyclobutane 4b crystallized from water in the monoclinic space group P21/n, and the derivative 4c crystallized from water in the

[1,3]/[1,4]-Sulfur atom migration in β-hydroxyalkylphosphine sulfides

• Katarzyna Włodarczyk,
• Piotr Borowski and
• Marek Stankevič

Beilstein J. Org. Chem. 2020, 16, 88–105, doi:10.3762/bjoc.16.11

• compounds failed to give single crystals for X-ray analysis. The presence of an oxygen atom attached to the phosphorus atom in the products could be deduced based on 1H and 13C NMR analysis. In the 1H NMR spectra of phosphine sulfide 12, the chemical shifts of the signals belonging to the aromatic protons

Halogen-bonding-induced diverse aggregation of 4,5-diiodo-1,2,3-triazolium salts with different anions

• Xingyu Xu,
• Shiqing Huang,
• Zengyu Zhang,
• Lei Cao and
• Xiaoyu Yan

Beilstein J. Org. Chem. 2020, 16, 78–87, doi:10.3762/bjoc.16.10

• evaporation of dichloromethane solution. The treatment of 2-I with 2 equivalents iodine or 4 equivalents iodine afforded triazolium polyiodide 2-I.1.5I2 and 2-I.3.5I2, respectively. The single crystals were obtained by slow diffusion of ether into a dichloromethane solution. The crystal X-ray analyses of 2-I

• ), 110.0, 21.4, 17.4; anal. calcd. for C22H22F3I2N3O2 (671.24): C, 39.37, H, 3.30, N, 6.26%; found: C, 39.51, H, 3.49, N, 6.18%. 2-I.1.5I2: 2-I (35 mg, 0.05 mol) and I2 (25 mg, 0.1 mmol) were mixed in dichloromethane (6 mL) in a round bottom flask. The single crystals were obtained by slow diffusion of

• mixed in dichloromethane (10 mL) in a round bottom flask. The single crystals were obtained by slow diffusion of ether into a dichloromethane solution, Brown solid, 63 mg, 81% yield. 1H NMR (400 MHz, CDCl3) δ 7.21 (s, 4H),2.48 (s, 6H), 2.10 (s, 12H); anal. calcd. for C22H22I10N3 (1073.46): C, 15.72, H

Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles

• Sara Tejera,
• Giada Caniglia,
• Rosa L. Dorta,
• Andrea Favero,
• Javier González-Platas and
• Jesús T. Vázquez

Beilstein J. Org. Chem. 2019, 15, 2881–2888, doi:10.3762/bjoc.15.282

• 12 led to single crystals suitable for X-ray crystallography. Its analysis (Figure 3) not only confirmed the structure, but in addition showed a well-organized crystal packing (Figure 4) where the alternate disposition of the molecules displayed a parallelism between the p-bromophenyl groups as well

Nanangenines: drimane sesquiterpenoids as the dominant metabolite cohort of a novel Australian fungus, Aspergillus nanangensis

• Heather J. Lacey,
• Cameron L. M. Gilchrist,
• Andrew Crombie,
• John A. Kalaitzis,
• Daniel Vuong,
• Peter J. Rutledge,
• Peter Turner,
• John I. Pitt,
• Ernest Lacey,
• Yit-Heng Chooi and
• Andrew M. Piggott

Beilstein J. Org. Chem. 2019, 15, 2631–2643, doi:10.3762/bjoc.15.256

• their conversion to 4-bromobenzoyl ester derivatives, with substitution at the C-9 and C-1 hydroxy groups respectively, and the growth of crystals of these derivatives (2b and 3b). The X-ray diffraction data obtained from single crystals of 4 and 9 did not allow a definitive determination of their

Formation of alkyne-bridged ferrocenophanes using ring-closing alkyne metathesis on 1,1’-diacetylenic ferrocenes

• Celine Bittner,
• Dirk Bockfeld and
• Matthias Tamm

Beilstein J. Org. Chem. 2019, 15, 2534–2543, doi:10.3762/bjoc.15.246

• disorder on the iron position. Unfortunately, no single crystals for X-ray diffraction analysis could be obtained with such disorder being absent. For the catalytic RCAM (Scheme 1), the substrates 1a and 1b were dissolved in toluene at high dilution (4.5 mM), and the catalyst MoF6 (2 mol %) was added as a

• remained in a mixture with excess monomer. Single crystals of compound 2b suitable for X-ray diffraction analysis could be obtained at room temperature from a DCM or CDCl3 solution layered with hexane, respectively. An ORTEP drawing of 2b is shown in Figure 6. The ferrocenophane crystallises in the

• can be seen in Figure 9. Single crystals of the silver complex 5 suitable for X-ray diffraction analysis could be obtained after layering a THF solution with hexane. The resulting ORTEP drawing is shown in Figure 10. The molecular structure of 5 turned out to be a coordination polymer with a rather

Self-assembled coordination thioether silver(I) macrocyclic complexes for homogeneous catalysis

• Zhen Cao,
• Aline Lacoudre,
• Cybille Rossy and
• Brigitte Bibal

Beilstein J. Org. Chem. 2019, 15, 2465–2472, doi:10.3762/bjoc.15.239

• for 1a, AgOTFA for 1b, AgNO3 for 1c and PPh3AgOTf for 1d. Crystallographic structures of silver complexes Single crystals of 1a, 1c and 1d suitable for X-ray diffraction analysis were grown from the slow diffusion of hexane into a solution of each complex in dichloromethane. Interestingly, each

Reversible switching of arylazopyrazole within a metal–organic cage

• Anton I. Hanopolskyi,
• Soumen De,
• Michał J. Białek,
• Yael Diskin-Posner,
• Liat Avram,
• Moran Feller and
• Rafal Klajn

Beilstein J. Org. Chem. 2019, 15, 2398–2407, doi:10.3762/bjoc.15.232

• protons are correlated with H1, H3, and H7, whereas the Hc protons are correlated with H4, H8, and H5 (see the partial NOE spectrum in Figure 2; see below for further analysis of this spectrum). Single crystals of (E-1)22 suitable for X-ray diffraction were obtained by slow water evaporation from an

In water multicomponent synthesis of low-molecular-mass 4,7-dihydrotetrazolo[1,5-a]pyrimidines

• Irina G. Tkachenko,
• Sergey A. Komykhov,
• Vladimir I. Musatov,
• Svitlana V. Shishkina,
• Viktoriya V. Dyakonenko,
• Vladimir N. Shvets,
• Mikhail V. Diachkov,
• Valentyn A. Chebanov and
• Sergey M. Desenko

Beilstein J. Org. Chem. 2019, 15, 2390–2397, doi:10.3762/bjoc.15.231

• Irina G. Tkachenko Sergey A. Komykhov Vladimir I. Musatov Svitlana V. Shishkina Viktoriya V. Dyakonenko Vladimir N. Shvets Mikhail V. Diachkov Valentyn A. Chebanov Sergey M. Desenko State Scientific Institution "Institute for Single Crystals", National Academy of Sciences of Ukraine, Nauky Ave 60

Fluorinated azobenzenes as supramolecular halogen-bonding building blocks

• Esther Nieland,
• Oliver Weingart and
• Bernd M. Schmidt

Beilstein J. Org. Chem. 2019, 15, 2013–2019, doi:10.3762/bjoc.15.197

• the Supporting Information File 1, Figures S6–S8). In addition to that, slow evaporation of an equimolar solution of U1 and A2 in benzene furnished red-orange single crystals suitable for X-ray analysis of a [2 + 2] halogen-bonded box, U1···A2, over the course of a few days in quantitative yield

Synthesis and anion binding properties of phthalimide-containing corona[6]arenes

• Meng-Di Gu,
• Yao Lu and
• Mei-Xiang Wang

Beilstein J. Org. Chem. 2019, 15, 1976–1983, doi:10.3762/bjoc.15.193

• -corona[6]arenes in the solid state, high quality single crystals of 3a were grown at room temperature from diffusion of diethyl ether vapor into the solution of 3a in acetonitrile. X-ray diffraction analysis revealed that the macrocycle 3a adopted an interesting conformation. As depicted in Figure 1, it

• ability of 3a to bind various anion species in gas phase. To our delight, host molecule 3a co-crystalized with n-Bu4NX (X = Cl, Br) from diffusion of diethyl ether vapor into ethyl acetate solution at ambient temperature to give single crystals of the host–guest complexes (n-Bu4NX)3-3a (X = Cl, Br). X-ray

Tautomerism as primary signaling mechanism in metal sensing: the case of amide group

• Vera Deneva,
• Georgi Dobrikov,
• Aurelien Crochet,
• Daniela Nedeltcheva,
• Katharina M. Fromm and
• Liudmil Antonov

Beilstein J. Org. Chem. 2019, 15, 1898–1906, doi:10.3762/bjoc.15.185

• (Aldrich). X-ray crystallographic measurements Experimental Single crystals of 6 were crystallized from acetonitrile by slow evaporation. A suitable crystal was selected and was mounted on a loop in oil on a Stoe IPDS2T diffractometer. The crystallographic data of the single crystal were collected with Cu

Application of chiral 2-isoxazoline for the synthesis of syn-1,3-diol analogs

• Juanjuan Feng,
• Tianyu Li,
• Jiaxin Zhang and
• Peng Jiao

Beilstein J. Org. Chem. 2019, 15, 1840–1847, doi:10.3762/bjoc.15.179

• gave 16 in 87% yield [26][27]. The absolute stereochemistry of 16 was confirmed by crystal structure analysis [72] and the specific rotation [28] of 17. Centimeter-long prismatic single crystals of 17 were obtained by slow evaporation of a petroleum solution. Starting from 9, we tested several

Synthesis, photophysical and electrochemical properties of pyridine, pyrazine and triazine-based (D–π–)₂A fluorescent dyes

• Keiichi Imato,
• Toshiaki Enoki,
• Koji Uenaka and
• Yousuke Ooyama

Beilstein J. Org. Chem. 2019, 15, 1712–1721, doi:10.3762/bjoc.15.167

• dye molecules in the solid state, although we could not prepare single crystals of OUY-2, OUK-2 and OUJ-2 for the X-ray structural analysis. Electrochemical properties The electrochemical properties of OUY-2, OUK-2 and OUJ-2 were investigated by cyclic voltammetry (CV) in DMF containing 0.1 M

Selenophene-containing heterotriacenes by a C–Se coupling/cyclization reaction

• Pierre-Olivier Schwartz,
• Sebastian Förtsch,
• Astrid Vogt,
• Elena Mena-Osteritz and
• Peter Bäuerle

Beilstein J. Org. Chem. 2019, 15, 1379–1393, doi:10.3762/bjoc.15.138

• accordance with data for selenophene compared to thiophene [35]. Single crystal X-ray structure analysis Single crystals of heterotriacenes DTS 2, DST 3, and DSS 4 suitable for X-ray structure analysis were obtained and details of the refinements are summarized in Tables S1-S3 (Supporting Information File 1

• ). X-ray structure analysis of DTT 1 was already published by Brédas et al. [36][37]. Single crystals of DTS 2 and DSS 4 as very thin crystalline needles were obtainned by careful sublimation. Both heterotriacenes crystallized in the monoclinic space group P21/c with 18 molecules in the unit cell (DTS

• 2: a = 5.978(3), b = 29.005(11), c = 21.173(8) Å; α = 90°, β = 91.903(19)°, γ = 90°, V = 3669(3) Å3; DSS 4: a = 6.108(3), b = 29.049(17), c = 21.949(11) Å; α = 90°, β = 91.815 (12)°, γ = 90°, V = 3892(3) Å3). The molecules in both crystals evidenced some rotational disorder. Single crystals of

Formation of an unexpected 3,3-diphenyl-3H-indazole through a facile intramolecular [2 + 3] cycloaddition of the diazo intermediate

• Andrew T. King,
• Hugh G. Hiscocks,
• Lidia Matesic,
• Mohan Bhadbhade,
• Roger Bishop and
• Alison T. Ung

Beilstein J. Org. Chem. 2019, 15, 1347–1354, doi:10.3762/bjoc.15.134

• the indazole ring. The ambiguity was overcome through the X-ray structural analysis of the compound. The single crystals were easily obtained by recrystallisation from CH2Cl2. Crystal structure analysis The X-ray crystal analysis revealed that the product was not the diazonium intermediate 7, but

Doebner-type pyrazolopyridine carboxylic acids in an Ugi four-component reaction

• Maryna V. Murlykina,
• Oleksandr V. Kolomiets,
• Maryna M. Kornet,
• Yana I. Sakhno,
• Sergey M. Desenko,
• Victoriya V. Dyakonenko,
• Svetlana V. Shishkina,
• Oleksandr A. Brazhko,
• Vladimir I. Musatov,
• Alexander V. Tsygankov,
• Erik V. Van der Eycken and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2019, 15, 1281–1288, doi:10.3762/bjoc.15.126

• , State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Nauky Ave., 60, 61072, Kharkiv, Ukraine Faculty of Chemistry, V. N. Karazin Kharkiv National University, Svobody sq., 4, 61077, Kharkiv, Ukraine Laboratory for Organic & Microwave-Assisted Chemistry

Insertion of [1.1.1]propellane into aromatic disulfides

• Robin M. Bär,
• Gregor Heinrich,
• Martin Nieger,
• Olaf Fuhr and
• Stefan Bräse

Beilstein J. Org. Chem. 2019, 15, 1172–1180, doi:10.3762/bjoc.15.114

• obtain single-crystals of 14 to confirm the structure by X-ray diffraction (Scheme 4) [31]. The rod-like structure of the [2]staffane unit now becomes more tangible. The distance in one BCP unit equals 1.857(3) Å (C1–C5) and the two units are 1.491(4) Å apart from each other (C1–C1’). Reaction with

Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds

• Victoria V. Lipson,
• Tetiana L. Pavlovska,
• Nataliya V. Svetlichnaya,
• Anna A. Poryvai,
• Nikolay Yu. Gorobets,
• Erik V. Van der Eycken,
• Irina S. Konovalova,
• Svetlana V. Shiskina,
• Alexander V. Borisov,
• Vladimir I. Musatov and
• Alexander V. Mazepa

Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101

• Victoria V. Lipson Tetiana L. Pavlovska Nataliya V. Svetlichnaya Anna A. Poryvai Nikolay Yu. Gorobets Erik V. Van der Eycken Irina S. Konovalova Svetlana V. Shiskina Alexander V. Borisov Vladimir I. Musatov Alexander V. Mazepa SSI “Institute for Single Crystals” of National Academy of Sciences of

Coordination chemistry and photoswitching of dinuclear macrocyclic cadmium-, nickel-, and zinc complexes containing azobenzene carboxylato co-ligands

• Jennifer Klose,
• Tobias Severin,
• Peter Hahn,
• Alexander Jeremies,
• Jens Bergmann,
• Daniel Fuhrmann,
• Jan Griebel,
• Bernd Abel and
• Berthold Kersting

Beilstein J. Org. Chem. 2019, 15, 840–851, doi:10.3762/bjoc.15.81

• confirmation regarding the composition and structures of the complexes were obtained by single crystal X-ray diffraction studies. Single crystals could be obtained for the tetraphenylborates 3' and 8 and perchlorate salts 5–7. The molecular structures of the complexes are displayed in Figures 4–8. Selected

• an applied magnetic field of 0.5 and 1.0 Tesla. The observed susceptibility data were corrected for underlying diamagnetism. The synthesis of the complexes are shown in Supporting Information File 1. X-ray crystallography. Single crystals of 3', 5–8 suitable for X-ray crystallography were selected

Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors

• Kirill B. Polyanskii,
• Kseniia A. Alekseeva,
• Pavel V. Raspertov,
• Pavel A. Kumandin,
• Eugeniya V. Nikitina,
• Atash V. Gurbanov and
• Fedor I. Zubkov

Beilstein J. Org. Chem. 2019, 15, 769–779, doi:10.3762/bjoc.15.73

• were obtained as good crystals suitable for X-ray diffraction analysis. Unfortunately, we were not able to obtain single crystals of satisfactory quality for the morpholino-containing catalyst 11d. Still, the accessible X-ray structural information is sufficient to correlate structure with catalytic

Catalyst-free assembly of giant tris(heteroaryl)methanes: synthesis of novel pharmacophoric triads and model sterically crowded tris(heteroaryl/aryl)methyl cation salts

• Rodrigo Abonia,
• Luisa F. Gutiérrez,
• Braulio Insuasty,
• Jairo Quiroga,
• Kenneth K. Laali,
• Chunqing Zhao,
• Gabriela L. Borosky,
• Samantha M. Horwitz and
• Scott D. Bunge

Beilstein J. Org. Chem. 2019, 15, 642–654, doi:10.3762/bjoc.15.60

• 1D and 2D NMR spectroscopy and by EIMS, elemental analysis, and HRMS (see experimental section and Supporting Information File 1). Additionally, single crystals of compound 9{4,7,1} suitable for X-ray analysis were grown from ACN at room temperature. Compound 9{4,7,1} crystallizes in the triclinic

Synthesis of mono-functionalized S-diazocines via intramolecular Baeyer–Mills reactions

• Miriam Schehr,
• Daniel Hugenbusch,
• Tobias Moje,
• Christian Näther and
• Rainer Herges

Beilstein J. Org. Chem. 2018, 14, 2799–2804, doi:10.3762/bjoc.14.257

• -functionalized S-diazocine 3 single crystals could be obtained, which were characterized by single crystal X-ray diffraction. The structure of 3 is the first crystal structure of a S-diazocine reported in the Cambridge Structural Database (CSD; version 5.39; Feb. 2018) [28]. This compound crystallizes in the

Transition metal-free oxidative and deoxygenative C–H/C–Li cross-couplings of 2H-imidazole 1-oxides with carboranyl lithium as an efficient synthetic approach to azaheterocyclic carboranes

• Lidia A. Smyshliaeva,
• Mikhail V. Varaksin,
• Pavel A. Slepukhin,
• Oleg N. Chupakhin and
• Valery N. Charushin

Beilstein J. Org. Chem. 2018, 14, 2618–2626, doi:10.3762/bjoc.14.240

• be attributed to C-2 of the imidazole ring. The structure of imidazolyl carborane 5d has also been proved by the X-ray analysis (Figure 3). The single crystals were obtained by slow evaporation of imidazolyl carborane 5d from a mixture of CH2Cl2/heptane, 8:2. According to the XRD data, two

Some mechanistic aspects regarding the Suzuki–Miyaura reaction between selected ortho-substituted phenylboronic acids and 3,4,5-tribromo-2,6-dimethylpyridine

• Piotr Pomarański,
• Piotr Roszkowski,
• Jan K. Maurin,
• Armand Budzianowski and
• Zbigniew Czarnocki

Beilstein J. Org. Chem. 2018, 14, 2384–2393, doi:10.3762/bjoc.14.214

• possible by careful crystallization from methanol. The structure and configuration of the products 12–14 were established by NMR as well as the single-crystals X-ray analysis (see Supporting Information File 1 for details). The data presented in Table 4 clearly indicate that the substituent change from