Synthesis, fluorescence properties and the promising cytotoxicity of pyrene–derived aminophosphonates

• Jarosław Lewkowski,
• Maria Rodriguez Moya,
• Anna Wrona-Piotrowicz,
• Janusz Zakrzewski,
• Renata Kontek and
• Gabriela Gajek

Beilstein J. Org. Chem. 2016, 12, 1229–1235, doi:10.3762/bjoc.12.117

• isopropylamine) was present in the reaction mixture (Scheme 1). All obtained aminophosphonates 3Aa–j, 3Ba–e, 3Ca–d and 3Cg as well as the hydroxyphosphonate 5A gave satisfactory results of in the elemental analysis and were characterized by means of 1H, 13C and 31P NMR and IR spectroscopy with all signals

• dichloromethane. After 24-hours reaction, the reaction was quenched by methanol to give, after routine work-up the desired acids 4a and 4c (Scheme 1). They were characterized by NMR spectroscopy (1H, 13C and 31P), IR spectroscopy, melting point measurements and elemental analysis. The obtained phosphonic

1H-Imidazol-4(5H)-ones and thiazol-4(5H)-ones as emerging pronucleophiles in asymmetric catalysis

• Antonia Mielgo and
• Claudio Palomo

Beilstein J. Org. Chem. 2016, 12, 918–936, doi:10.3762/bjoc.12.90

• 2012 supported by Schreiner [91] after an exhaustive study based on NMR/IR spectroscopy, mass spectrometry and theoretical DFT calculations. By taking into account these characteristics, the authors considered that the combination of ureidopetide’s structure, which have been recognized by their ability

A convenient route to symmetrically and unsymmetrically substituted 3,5-diaryl-2,4,6-trimethylpyridines via Suzuki–Miyaura cross-coupling reaction

• Dariusz Błachut,
• Joanna Szawkało and
• Zbigniew Czarnocki

Beilstein J. Org. Chem. 2016, 12, 835–845, doi:10.3762/bjoc.12.82

• GC–MS analysis All isolated products were characterized by 1H NMR, 13C NMR, IR spectroscopy and MS and HR-MS spectrometry. The examination of the 1H NMR spectra of pyridine 22 revealed the presence the separated signals of methyl groups at position C-2, C-6 and 2-methylthio groups attached to the

Strecker degradation of amino acids promoted by a camphor-derived sulfonamide

• M. Fernanda N. N. Carvalho,
• M. João Ferreira,
• Ana S. O. Knittel,
• Maria da Conceição Oliveira,
• João Costa Pessoa,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2016, 12, 732–744, doi:10.3762/bjoc.12.73

• compensated in the products 7a, 7b and 8, respectively (Figure 7). A mechanism of the type 5 → 7 (azomethine ylide route) has been proposed for the ninhydrin reaction [30] and other Strecker-type degradation processes [31]. Oxazolidin-5-ones were shown by IR spectroscopy to be formed from amino acids and

Opportunities and challenges for direct C–H functionalization of piperazines

• Zhishi Ye,
• Kristen E. Gettys and
• Mingji Dai

Beilstein J. Org. Chem. 2016, 12, 702–715, doi:10.3762/bjoc.12.70

• N-Boc-piperazine 10 using a combination of sec-BuLi and 28 to produce (S)-30 with an 89:11 er. In 2015, O’Brien and co-workers expanded this work and reported an elegant and detailed study of asymmetric lithiation trapping of N-Boc-piperazines [43]. With the help of in situ IR spectroscopy, they

New synthetic strategies for xanthene-dye-appended cyclodextrins

• Milo Malanga,
• Andras Darcsi,
• Mihaly Balint,
• Gabor Benkovics,
• Tamas Sohajda and
• Szabolcs Beni

Beilstein J. Org. Chem. 2016, 12, 537–548, doi:10.3762/bjoc.12.53

• inexpensive dyes, we prepared rhodamine- and fluorescein-appended cyclodextrins. The compounds were characterized by NMR and IR spectroscopy and MS spectrometry, their UV–vis spectra were recorded at various pH, and their purity was determined by capillary electrophoresis. Two potential models for the

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• version and are not only used in IR spectroscopy but also on the preparative scale for homogenization and cracking solid components. The common weakness of these simple accessories is the critical rotation/mixing speed, which can be overcome by a new generation of equipment; planetary BM, that consist of

Solving the puzzling competition of the thermal C²–C⁶ vs Myers–Saito cyclization of enyne-carbodiimides

• Anup Rana,
• Mehmet Emin Cinar,
• Debabrata Samanta and
• Michael Schmittel

Beilstein J. Org. Chem. 2016, 12, 43–49, doi:10.3762/bjoc.12.6

• assignment of which was further confirmed by 1H, 13C, 1H,1H-COSY NMR and also by IR spectroscopy and mass spectrometry. For 14, a broad singlet at 10.02 ppm that is characteristic for its NH proton was observed in the crude NMR mixture. In summary, the Myers–Saito product 12 was produced as major product, 67

Rhodium, iridium and nickel complexes with a 1,3,5-triphenylbenzene tris-MIC ligand. Study of the electronic properties and catalytic activities

• Carmen Mejuto,
• Beatriz Royo,
• Gregorio Guisado-Barrios and
• Eduardo Peris

Beilstein J. Org. Chem. 2015, 11, 2584–2590, doi:10.3762/bjoc.11.278

• obtaining a series of Rh(I), Ir(I) and Ni(II) complexes. Interestingly, the tris-MIC complex of Ni is the first trimetallic Ni complex with a tris-carbene ligand. The electron-donating properties of the ligand were assessed by cyclic voltammetry and by IR spectroscopy of the corresponding carbonylated tris

Easy access to heterobimetallic complexes for medical imaging applications via microwave-enhanced cycloaddition

• Nicolas Desbois,
• Sandrine Pacquelet,
• Adrien Dubois,
• Clément Michelin and
• Claude P. Gros

Beilstein J. Org. Chem. 2015, 11, 2202–2208, doi:10.3762/bjoc.11.239

• preparation of bimetallic compounds 5–7 as shown in Table 1. The reaction conditions used for all the reported examples were identical to those for 5a, and the yields were from moderate to good. All the final products were characterized by HRMS, UV–vis and IR spectroscopy. Relaxivity measurements The

2-Hetaryl-1,3-tropolones based on five-membered nitrogen heterocycles: synthesis, structure and properties

• Yury A. Sayapin,
• Inna O. Tupaeva,
• Alexandra A. Kolodina,
• Eugeny A. Gusakov,
• Vitaly N. Komissarov,
• Igor V. Dorogan,
• Nadezhda I. Makarova,
• Anatoly V. Metelitsa,
• Valery V. Tkachev,
• Sergey M. Aldoshin and
• Vladimir I. Minkin

Beilstein J. Org. Chem. 2015, 11, 2179–2188, doi:10.3762/bjoc.11.236

• been characterized by 1H NMR, IR spectroscopy and mass spectrometry and also by the X-ray diffraction studies of the two compounds 5g and 6e, representing trichloro- and tetrachloro derivatives of the prepared tropolones. The overall views of the molecules are shown in Figure 1 and Figure 2

A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines

• Mingxing Liu,
• Jiarong Li,
• Hongxin Chai,
• Kai Zhang,
• Deli Yang,
• Qi Zhang and
• Daxin Shi

Beilstein J. Org. Chem. 2015, 11, 2125–2131, doi:10.3762/bjoc.11.229

• -component condensation of hydrazines, methylenemalononitriles, aldehydes and alcohols has been developed via two different reaction pathways. The structures of target products were characterized by IR spectroscopy, NMR (1H and 13C) spectroscopy and HRMS (ESI) spectrometry. The crystal structure of 4-ethoxy

Fe(II)/Et₃N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives

• Ekaterina E. Galenko,
• Olesya A. Tomashenko,
• Alexander F. Khlebnikov,
• Mikhail S. Novikov and
• Taras L. Panikorovskii

Beilstein J. Org. Chem. 2015, 11, 1732–1740, doi:10.3762/bjoc.11.189

• for 6–7 h at 45 °C, gave 5-alkoxycarbonylpyrrol-3-ylimidazolium bromides 1 in reasonable yields (Table 1). All new compounds were characterized by 1H and 13C NMR, IR spectroscopy, and mass spectrometry. 1-Benzyl-3-(1H-pyrrol-3-yl)-1H-imidazol-3-ium bromides 1 can be easily debenzylated on Pd/C, with

Tetrathiafulvalene-based azine ligands for anion and metal cation coordination

• Awatef Ayadi,
• Aziz El Alamy,
• Olivier Alévêque,
• Magali Allain,
• Nabil Zouari,
• Mohammed Bouachrine and
• Abdelkrim El-Ghayoury

Beilstein J. Org. Chem. 2015, 11, 1379–1391, doi:10.3762/bjoc.11.149

• desired ligands L1 and L2 in 75% and 63% isolated yields, respectively. The structures of the new ligands were characterized by 1H and 13C NMR, UV–visible and IR spectroscopy, high resolution mass spectrometry and elemental analysis. Crystal structure description Details about data collection and

Carboxylated dithiafulvenes and tetrathiafulvalene vinylogues: synthesis, electronic properties, and complexation with zinc ions

• Yunfei Wang and
• Yuming Zhao

Beilstein J. Org. Chem. 2015, 11, 957–965, doi:10.3762/bjoc.11.107

• coordination polymer is considerably reduced in comparison with the smaller-sized Zn-DTF complex. The structural properties of Zn-TTFV coordination polymer 8 and Zn-DTF complex 9 were examined by IR spectroscopy (Figure 3). Compared with the IR spectra of carboxyl-TTFV 6 and carboxyl-DTF 7, the vibrational

Synthesis and characterization of the cyanobenzene-ethylenedithio-TTF donor

• Sandrina Oliveira,
• Dulce Belo,
• Isabel C. Santos,
• Sandra Rabaça and
• Manuel Almeida

Beilstein J. Org. Chem. 2015, 11, 951–956, doi:10.3762/bjoc.11.106

• voltammetry, NMR, UV-visible and IR spectroscopy. Keywords: cross-coupling; cyanobenzene; cyclic voltammetry; dissymmetric tetrathiafulvalene; electro-active donors; Introduction The tetrathiafulvalene molecule (TTF) and its many derivatives, due to its unique π-donor properties, have been at the basis of

• , UV–vis and IR spectroscopy, mass spectrometry and elemental analysis. In the IR spectra of 3, the characteristic C≡N and C=C stretching absorption bands appeared around 2229 cm−1 and 1637 and 1446 cm−1, respectively. The 1H NMR spectra showed signals at 7.48–7.31 and 3.33 ppm, integrating with ratios

Multivalent polyglycerol supported imidazolidin-4-one organocatalysts for enantioselective Friedel–Crafts alkylations

• Tommaso Pecchioli,
• Manoj Kumar Muthyala,
• Rainer Haag and
• Mathias Christmann

Beilstein J. Org. Chem. 2015, 11, 730–738, doi:10.3762/bjoc.11.83

• reaction was monitored by IR spectroscopy and TLC. Purification of the products 4a–c was carried out by washing with aqueous saturated EDTA solution followed by dialysis in methanol/chloroform mixture for 24 h, and then in methanol and chloroform, respectively, for additional 12 h each. The catalyst

Probing multivalency in ligand–receptor-mediated adhesion of soft, biomimetic interfaces

• Stephan Schmidt,
• Hanqing Wang,
• Daniel Pussak,
• Simone Mosca and
• Laura Hartmann

Beilstein J. Org. Chem. 2015, 11, 720–729, doi:10.3762/bjoc.11.82

• acid in PEG-SCPs The carboxylic acids in the PEG-SCPs were quantified by titration with TBO, zeta potential measurements and IR spectroscopy. The TBO measurement was conducted as follows. 1.5 mL of PEG-SCP dispersion were centrifuged and a solution of 0.5 mM TBO solution (pH 10.3) was added to the

Functionalized branched EDOT-terthiophene copolymer films by electropolymerization and post-polymerization “click”-reactions

• Miriam Goll,
• Adrian Ruff,
• Erna Muks,
• Felix Goerigk,
• Beatrice Omiecienski,
• Ines Ruff,
• Rafael C. González-Cano,
• Juan T. Lopez Navarrete,
• M. Carmen Ruiz Delgado and
• Sabine Ludwigs

Beilstein J. Org. Chem. 2015, 11, 335–347, doi:10.3762/bjoc.11.39

• with 1-hexyne and SO3Na-alkyne (yielding a butyl end group or a sulfonate end group, respectively). DMSO was chosen as solvent as the degree of swelling is very high [58] and allows modification of the bulk of the film and not just of the surface. The modified films were analyzed by IR spectroscopy in

• a combined reflection/absorption mode (RAS) (Figure 3B). The disappearance of the characteristic azide-band at 2100 cm−1 indicates that the cycloaddition-reaction takes place almost quantitatively (within the detection limit of IR spectroscopy). For the butyl-modified film P(EDOT-clickHex-co-3T)-1:1

• ]. Methods 1H (250 MHz) and 13C{1H} (63 MHz) NMR spectra were recorded on a Bruker Avance 250 spectrometer. vis-NIR spectra of the polymer films deposited on ITO-coated glass substrates were recorded with a Lambda 35 spectrometer (Bruker). IR spectroscopy was performed on a Bruker FTIR spectrometer IFS 66/S

Anion effect controlling the selectivity in the zinc-catalysed copolymerisation of CO₂ and cyclohexene oxide

• Sait Elmas,
• Muhammad Afzal Subhani,
• Walter Leitner and
• Thomas E. Müller

Beilstein J. Org. Chem. 2015, 11, 42–49, doi:10.3762/bjoc.11.7

• . Copolymerisation of CO2 and cyclohexene oxide with binuclear [LZn2](X)2 complexes Complexes 1 and 2 were then evaluated as catalysts in the copolymerisation of CO2 and cyclohexene oxide CHO (Scheme 3). To obtain insight into the kinetics, the progress of the reactions was monitored with in situ IR spectroscopy and

• . Köhler for scientific discussions and P. T. Kühn for synthesising the complexes. D. Engels and C. Minnich (S-PACT GmbH) are gratefully acknowledged for their contribution to in situ IR spectroscopy. M. Krautschick and V. Marker are thanked for experimental support.

Detonation nanodiamonds biofunctionalization and immobilization to titanium alloy surfaces as first steps towards medical application

• Juliana P. L. Gonçalves,
• Afnan Q. Shaikh,
• Manuela Reitzig,
• Daria A. Kovalenko,
• Jan Michael,
• René Beutner,
• Gianaurelio Cuniberti,
• Dieter Scharnweber and
• Jörg Opitz

Beilstein J. Org. Chem. 2014, 10, 2765–2773, doi:10.3762/bjoc.10.293

• qualitative analysis of the efficiency of the synthesis achieved on the surface of DND, represented in Scheme 1. Table S1 (please see the Supporting Information File 1) summarizes the characteristic absorption bands of the qualitative analysis from the synthesized species by IR spectroscopy [40][41]. The

Synthesis and characterization of a hyper-branched water-soluble β-cyclodextrin polymer

• Francesco Trotta,
• Fabrizio Caldera,
• Roberta Cavalli,
• Andrea Mele,
• Carlo Punta,
• Lucio Melone,
• Franca Castiglione,
• Barbara Rossi,
• Monica Ferro,
• Vincenza Crupi,
• Domenico Majolino,
• Valentina Venuti and
• Dominique Scalarone

Beilstein J. Org. Chem. 2014, 10, 2586–2593, doi:10.3762/bjoc.10.271

• resolution was about 0.28 cm−1/pixel. Fourier transform IR spectroscopy (FTIR) or attenuated total reflectance (ATR) absorption measurements were performed on dried samples, in the 600–4000 cm−1 wavenumber range and at room temperature. Spectra were recorded using a Bomem DA8 Fourier transform spectrometer

Phosphinocyclodextrins as confining units for catalytic metal centres. Applications to carbon–carbon bond forming reactions

• Matthieu Jouffroy,
• Rafael Gramage-Doria,
• David Sémeril,
• Dominique Armspach,
• Dominique Matt,
• Werner Oberhauser and
• Loïc Toupet

Beilstein J. Org. Chem. 2014, 10, 2388–2405, doi:10.3762/bjoc.10.249

• candidates for hydroformylation studies. High-pressure NMR studies Upon subjecting complex 13 to a syngas (1:1 CO/H2 mixture) pressure of 40 bar at 80 °C in toluene-d8 (Scheme 7), the only species that was detected by high-pressure NMR and IR spectroscopy [44] was complex trans-[RhH(HUGPHOS-2)(CO)3] (14

Isoxazolium N-ylides and 1-oxa-5-azahexa-1,3,5-trienes on the way from isoxazoles to 2H-1,3-oxazines

• Alexander F. Khlebnikov,
• Mikhail S. Novikov,
• Yelizaveta G. Gorbunova,
• Ekaterina E. Galenko,
• Kirill I. Mikhailov,
• Viktoriia V. Pakalnis and
• Margarita S. Avdontceva

Beilstein J. Org. Chem. 2014, 10, 1896–1905, doi:10.3762/bjoc.10.197

• were verified by 1H NMR, 13C NMR, IR spectroscopy, HRMS, and elemental analysis. The structures of compounds 3a,k were additionally confirmed by X-ray analysis (Figure 3). The characteristic feature of the structure of compound 3a is the pseudo-axial position of the methoxycarbonyl group. The structure

• structures of compounds 4a–f were verified by 1H, 13C NMR, IR spectroscopy, and HRMS. Furthermore, the structures of compounds 4a,b were confirmed by X-ray analysis (Figure 4). According to 1H NMR no corresponding 1,3-oxazines were formed. Thus, only reactions of carbenoids with 5-alkoxy-substituted

Synthesis of new, highly luminescent bis(2,2’-bithiophen-5-yl) substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole and 1,2,4-triazole

• Anastasia S. Kostyuchenko,
• Vyacheslav L.Yurpalov,
• Aleksandra Kurowska,
• Wojciech Domagala,
• Adam Pron and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2014, 10, 1596–1602, doi:10.3762/bjoc.10.165

• % yield (Scheme 5). All intermediate and final products were identified by elemental analysis, NMR and IR spectroscopy (see Supporting Information File 1). Spectroscopic and luminescent properties of the synthesized compounds The target molecules 13, 14, 15 and 18 feature light absorption in the near