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

• . Supporting Information Supporting Information File 81: Experimental spectra for compound 2: FTIR, NMR (1H, 13C, DEPT, HMBC, HSQC, NOESY), ESIMS and the proposed fragmentation mechanism for 2 and 12. Supporting Information File 82: Calculations of the NMR chemical shifts for the assignment of the configuration

Simple activation by acid of latent Ru-NHC-based metathesis initiators bearing 8-quinolinolate co-ligands

• Julia Wappel,
• Roland C. Fischer,
• Luigi Cavallo,
• Christian Slugovc and
• Albert Poater

Beilstein J. Org. Chem. 2016, 12, 154–165, doi:10.3762/bjoc.12.17

• , 230–400 mesh. TLC was performed on aluminum sheets, Merck 60F 254. NMR (1H, 13C) spectra were recorded on a Bruker Avance 300 MHz or an INOVA 500 MHz spectrometer, in CDCl3 as the solvent. The solvent peak of residual CHCl3 was used for referencing the NMR spectra to 7.26 (1H) and 77.16 ppm (13C

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

Aerobic addition of secondary phosphine oxides to vinyl sulfides: a shortcut to 1-hydroxy-2-(organosulfanyl)ethyl(diorganyl)phosphine oxides

• Svetlana F. Malysheva,
• Alexander V. Artem’ev,
• Nina K. Gusarova,
• Nataliya A. Belogorlova,
• Alexander I. Albanov,
• C. W. Liu and
• Boris A. Trofimov

Beilstein J. Org. Chem. 2015, 11, 1985–1990, doi:10.3762/bjoc.11.214

• moisture-stable powders (3a–f) or oils (3g,h), soluble in common organic solvents. Their structures have been established by X-ray diffraction (for 3d, Figure 1), NMR (1H, 13C, 31P, 1H,13C-HSQC) and FTIR techniques. The presence of an asymmetric carbon atom in the reaction products leads to non-equivalence

A new and efficient procedure for the synthesis of hexahydropyrimidine-fused 1,4-naphthoquinones

• Marcelo Isidoro P. Reis,
• Vinícius R. Campos,
• Jackson A. L. C. Resende,
• Fernando C. Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2015, 11, 1235–1240, doi:10.3762/bjoc.11.137

• N,S-acetals. These compounds were obtained in good yields, and several of them showed promising antibacterial activity [42]. The structures of the synthesized 1,3,5-triazinanes were confirmed by spectroscopic techniques such as NMR, 1H and 13C-APT, infrared spectroscopy (FTIR) and high resolution

Synthesis of icariin from kaempferol through regioselective methylation and para-Claisen–Cope rearrangement

• Qinggang Mei,
• Chun Wang,
• Zhigang Zhao,
• Weicheng Yuan and
• Guolin Zhang

Beilstein J. Org. Chem. 2015, 11, 1220–1225, doi:10.3762/bjoc.11.135

• , respectively. The compounds 14, 2 and 1 were fully characterized by ESI-HRMS, 1H NMR, 13C NMR, 1H,1H COSY, 1H,13C HMBC/HSQC and IR (see Supporting Information File 1 for experimental and spectral data). In icariin (1), the configurations of the anomeric C-atoms of rhamnose and glocuse were α and β on the basis

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

• in CH2Cl2 with [n-Bu4][PF6] 0.1 M, E in V vs Ag/AgNO3 with scan rate = 100 mV s−1. Supporting Information Supporting Information File 202: NMR (1H and 13C), infrared spectra, UV–vis absorption spectra and short contact list of CNB-EDT-TTF. Acknowledgements We thank Dr. Joaquim Marçalo for the Mass

N-Alkyl derivatives of diosgenyl 2-amino-2-deoxy-β-D-glucopyranoside; synthesis and antimicrobial activity

• Agata Walczewska,
• Daria Grzywacz,
• Dorota Bednarczyk,
• Małgorzata Dawgul,
• Andrzej Nowacki,
• Wojciech Kamysz,
• Beata Liberek and
• Henryk Myszka

Beilstein J. Org. Chem. 2015, 11, 869–874, doi:10.3762/bjoc.11.97

• mixtures (Scheme 2). The respective mixtures of mono- and dialkylated products were separated. Structures of the N-alkylated derivatives of 7 were confirmed by the NMR (1H and 13C) spectroscopy and mass spectrometry (see Supporting Information File 1). All of them, similarly to the parent diosgenyl

Preparation and evaluation of cyclodextrin polypseudorotaxane with PEGylated liposome as a sustained release drug carrier

• Kayoko Hayashida,
• Taishi Higashi,
• Daichi Kono,
• Keiichi Motoyama,
• Koki Wada and
• Hidetoshi Arima

Beilstein J. Org. Chem. 2014, 10, 2756–2764, doi:10.3762/bjoc.10.292

• (JEOL, Tokyo, Japan) in the range between 4,000 and 400 cm−1 with a resolution of 4 cm−1 and 16 scans. 1H NMR 1H NMR spectrum was taken at 25 °C on a JEOL α-500 FT-NMR (Tokyo, Japan) operating at 500 MHz by using a 5 mm sample tube. Deuterated DMSO (DMSO-d6) was used as a solvent. The stoichiometry of

Synthesis of trifluoromethyl-substituted pyrazolo[4,3-c]pyridines – sequential versus multicomponent reaction approach

• Barbara Palka,
• Angela Di Capua,
• Maurizio Anzini,
• Gyté Vilkauskaité,
• Algirdas Šačkus and
• Wolfgang Holzer

Beilstein J. Org. Chem. 2014, 10, 1759–1764, doi:10.3762/bjoc.10.183

• all obtained products. Keywords: microwave-assisted reactions; multicomponent reactions; NMR (1H; 13C; 15N; 19F); Sonogashira coupling; trifluoromethylpyrazoles; Introduction Fluorine-containing compounds play an important role in medicinal and pharmaceutical chemistry as well as in agrochemistry [1

Synthesis, characterization and DNA interaction studies of new triptycene derivatives

• Sourav Chakraborty,
• Snehasish Mondal,
• Rina Kumari,
• Sourav Bhowmick,
• Prolay Das and
• Neeladri Das

Beilstein J. Org. Chem. 2014, 10, 1290–1298, doi:10.3762/bjoc.10.130

• hydrochloric acid and subsequent reaction with sodium azide yielded the triazidotriptycene 3 and 4 in 81% and 76% yield respectively. The newly synthesized triethynyltriptycenes (TETs) and triazidotriptycenes (TATs) were characterized by FTIR, multinuclear NMR (1H and 13C), LRMS, and elemental analyses. In

Cyclization of substitued 2-(2-fluorophenylazo)azines to azino[1,2-c]benzo[d][1,2,4]triazinium derivatives

• Aleksandra Jankowiak,
• Emilia Obijalska and
• Piotr Kaszynski

Beilstein J. Org. Chem. 2013, 9, 1873–1880, doi:10.3762/bjoc.9.219

• ); anal. calcd for C19H16FN3O3S: C, 59.21; H, 4.18; N, 10.90; found: C, 58.92; H, 4.09; N, 10.95. 7,9-Difluoro-3-methylpyrido[2,1-c][1,2,4]benzotriazin-11-ium chloride (1d): Method B, yield 40–80% (based on NMR): 1H NMR (300 MHz, CD3CN) δ 2.98 (s, 3H), 7.99 (t, J = 8.1 Hz, 1H), 8.49 (d, J = 5.5 Hz, 1H

Raman spectroscopy as a tool for monitoring mesoscale continuous-flow organic synthesis: Equipment interface and assessment in four medicinally-relevant reactions

• Trevor A. Hamlin and
• Nicholas E. Leadbeater

Beilstein J. Org. Chem. 2013, 9, 1843–1852, doi:10.3762/bjoc.9.215

• 298 K on either a Bruker DRX-400 MHz NMR, or Bruker Avance 500 MHz NMR. 1H NMR Spectra obtained in CDCl3 were referenced to residual non-deuterated chloroform (7.26 ppm) in the deuterated solvent. 13C NMR Spectra obtained in CDCl3 were referenced to chloroform (77.3 ppm). 19F NMR spectra were

Quantification of N-acetylcysteamine activated methylmalonate incorporation into polyketide biosynthesis

• Stephan Klopries,
• Uschi Sundermann and
• Frank Schulz

Beilstein J. Org. Chem. 2013, 9, 664–674, doi:10.3762/bjoc.9.75

• Accela HPLC-System (column Hypersil Gold, length 50 mm, inside diameter 1 mm, particle size 1.9 µm, ionization method: Electrospray Ionization). Products were characterized by NMR (1H, 13C) and HRMS. ESI-method for quantification of D3-label incorporation Mass-to-charge ratios of the extracts were

Self-assembly of Ru₄ and Ru₈ assemblies by coordination using organometallic Ru(II)₂ precursors: Synthesis, characterization and properties

• Sankarasekaran Shanmugaraju,
• Dipak Samanta and
• Partha Sarathi Mukherjee

Beilstein J. Org. Chem. 2012, 8, 313–322, doi:10.3762/bjoc.8.34

• single crystals of the macrocycle 2c have so far been unsuccessful. However, the analysis of multinuclear NMR (1H, 13C and 19F) in concurrence with the ESIMS study is fully consistent with the formation of a [4 + 2] self-assembled octanuclear metallacage. In view toward gaining further insight into the

Fluorescent hexaaryl- and hexa-heteroaryl[3]radialenes: Synthesis, structures, and properties

• Antonio Avellaneda,
• Courtney A. Hollis,
• Xin He and
• Christopher J. Sumby

Beilstein J. Org. Chem. 2012, 8, 71–80, doi:10.3762/bjoc.8.7

• performed by the Adelaide Proteomics Centre using an LTQ Orbitrap XL ETD spectrometer. 1H NMR spectra were recorded on a Varian Gemini 300 MHz spectrometer (75 MHz for 13C NMR) or a Varian Inova 600 MHz spectrometer (150 MHz for 13C NMR). 1H NMR spectra recorded in CDCl3 were referenced to the internal

Intraannular photoreactions in pseudo-geminally substituted [2.2]paracyclophanes

• Henning Hopf,
• Vitaly Raev and
• Peter G. Jones

Beilstein J. Org. Chem. 2011, 7, 658–667, doi:10.3762/bjoc.7.78

• a colorless solid residue (333 mg, 98%) of hydrocarbon 22, as a mixture of stereoisomers, pure by NMR. 1H NMR (200 MHz, CDCl3) δ 6.53–6.26 (m, 8H), 5.35 (dd, 0.04H, J1 = 8.6, J2 = 15.5 Hz), 5.24 (dd, 0.30H, J1 = 8.7, J2 = 15.6 Hz), 4.77 (dd, 1.36H, J1 = 10.3, J2 = 11.3 Hz), 4.75 (dd, 0.30H, J1

Photoinduced electron-transfer chemistry of the bielectrophoric N-phthaloyl derivatives of the amino acids tyrosine, histidine and tryptophan

• Axel G. Griesbeck,
• Jörg Neudörfl and
• Alan de Kiff

Beilstein J. Org. Chem. 2011, 7, 518–524, doi:10.3762/bjoc.7.60

• , 2C), 132.9 (d, 1C), 134.5 (d, 2C), 138.4 (s, 1C), 167.9 (s, 2C, C4/C4’). 13: 80% (by 1H NMR); 1H NMR (300 MHz, DMSO-d6): δ (ppm) = 7.75 (s, 4H). 13C NMR (75 MHz, DMSO-d6): δ (ppm) = 123.0 (d, 2C), 132.1 (s, 2C), 134.7 (d, 2C), 167.2 (s, 2C). Photolysis of N-phthaloyl tryptophan (10). A 100 mL

New amphiphilic glycopolymers by click functionalization of random copolymers – application to the colloidal stabilisation of polymer nanoparticles and their interaction with concanavalin A lectin

• Otman Otman,
• Paul Boullanger,
• Eric Drockenmuller and
• Thierry Hamaide

Beilstein J. Org. Chem. 2010, 6, No. 58, doi:10.3762/bjoc.6.58

• fully characterized by IR (disappearance of ν(N3) at 2121 cm−1 and ν(C≡C) at 2129 cm−1) and NMR: 1H (δ H12 at 8.06 ppm) and 13C (δ C11 and C12 respectively, at 143.32 and 125.82 ppm). DEPT experiments were used to ascertain the chemical shifts and to ensure the complete conversion of the azide functions

1-(4-Alkyloxybenzyl)-3-methyl-1H-imidazol-3-ium organic backbone: A versatile smectogenic moiety

• William Dobbs,
• Laurent Douce and
• Benoît Heinrich

Beilstein J. Org. Chem. 2009, 5, No. 62, doi:10.3762/bjoc.5.62

• (n > 10) according to the chain length. All imidazolium compounds (18–68, 110–610, 112–612, 114–614, 116–616) were purified by flash chromatography or crystallization. Their structural characterizations and their purities were established by 1H NMR, 13C NMR{1H}, FT-IR spectroscopy and elemental

A convenient method for preparing rigid-core ionic liquid crystals

• Julien Fouchet,
• Laurent Douce,
• Benoît Heinrich,
• Richard Welter and
• Alain Louati

Beilstein J. Org. Chem. 2009, 5, No. 51, doi:10.3762/bjoc.5.51

• properties and mesomorphism, we prepared compounds with BF4− (1b), PF6− (1c), CF3SO3− (1d) and (CF3SO2)2N− (1e) anions in excellent yield by anion metathesis in water/CH2Cl2 as solvent (Scheme 4). All these compounds were fully characterized by 1H NMR, 13C NMR {1H}, FT-IR and UV spectroscopy, as well as

Synthesis of coumarin or ferrocene labeled nucleosides via Staudinger ligation

• Ivana Kosiova,
• Andrea Janicova and
• Pavol Kois

Beilstein J. Org. Chem. 2006, 2, No. 23, doi:10.1186/1860-5397-2-23

• structures of the products were confirmed by 1H and 13C NMR, 1H-1H COSY and 13C-1H HSQC analysis. The signal due to the NH-function of the newly created amide bond was clearly visible in all cases. We expected analogous results in the reactions of 5'-azido-5'-deoxyuridine. Surprisingly, the reactions of this

• . Analogous reaction of 4-ferrocenyl-4-oxobutanoic acid reactive ester with iminophoshorane nucleoside derivative 7 gave 2'-ferrocene labeled uridine (Scheme 3). The yield of pure isolated product 18 was 57% and its structure was confirmed by 1H and 13C NMR, 1H-1H COSY and 13C-1H HSQC analysis. Conclusion We