A concise flow synthesis of indole-3-carboxylic ester and its derivatisation to an auxin mimic

• Marcus Baumann,
• Ian R. Baxendale and
• Fabien Deplante

Beilstein J. Org. Chem. 2017, 13, 2549–2560, doi:10.3762/bjoc.13.251

• % of tallest signal). Low and high-resolution mass spectrometry was performed using the indicated techniques on instruments equipped with Acquity UPLC and a lock-mass electrospray ion source. For accurate mass measurements the deviation from the calculated formula is reported in ppm. Melting points

The chemistry and biology of mycolactones

• Matthias Gehringer and
• Karl-Heinz Altmann

Beilstein J. Org. Chem. 2017, 13, 1596–1660, doi:10.3762/bjoc.13.159

• activity. Further purification of this material by reversed-phase HPLC and subsequent characterization by high-resolution mass spectrometry and two-dimensional NMR spectroscopy unveiled a 12-membered macrolactone substituted with two polyketide-derived side chains (Figure 1). Based on its mycobacterial

• Leadlay and co-workers applying LC−sequential and high-resolution mass spectrometry in combination with deuterium exchange experiments [54]. Instead of the additional hydroxy group proposed by the Small group, these studies provided strong evidence for mycolactone D (3) to feature an extra methyl group at

• originally been proposed by the Small group (11, Figure 3) after partial TLC purification and subsequent high-resolution mass spectrometry and 1H NMR spectroscopy (although no NMR data are shown in their report) [50]. Shortly afterwards, the Leadlay group proposed structure 6 (Figure 2) based on tandem mass

1-Imidoalkylphosphonium salts with modulated C_α–P⁺ bond strength: synthesis and application as new active α-imidoalkylating agents

• Jakub Adamek,
• Roman Mazurkiewicz,
• Anna Węgrzyk and
• Karol Erfurt

Beilstein J. Org. Chem. 2017, 13, 1446–1455, doi:10.3762/bjoc.13.142

• , respectively, as zero ppm. All chemical shifts (δ) are reported in ppm, and coupling constants (J) are given in hertz (Hz). High-resolution mass spectrometry (HRMS) analyses were performed on a Waters Xevo G2 Q-TOF mass spectrometer equipped with an ESI source operating in the positive ion mode. The accurate

A speedy route to sterically encumbered, benzene-fused derivatives of privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline

• Olga Bakulina,
• Alexander Ivanov,
• Vitalii Suslonov,
• Dmitry Dar’in and
• Mikhail Krasavin

Beilstein J. Org. Chem. 2017, 13, 1413–1424, doi:10.3762/bjoc.13.138

• reaction with homophthalic anhydride (HPA). The compounds obtained contain a benzene-fused, privileged, naturally occurring hexahydropyrrolo[1,2-b]isoquinoline core and are distinctly encumbered from steric perspective. The novel compounds have been characterized by NMR spectroscopy, high-resolution mass

• spectrometry and X-ray crystallography and certain regularities in the NMR behavior have been established, leading a set of rules for stereochemical assignment based on the NMR data. A Mannich-type adduct between HPA and an imine (previously only postulated as a crucial intermediate en route to CCR products

Unpredictable cycloisomerization of 1,11-dien-6-ynes by a common cobalt catalyst

• Abdusalom A. Suleymanov,
• Dmitry V. Vasilyev,
• Valentin V. Novikov,
• Yulia V. Nelyubina and
• Dmitry S. Perekalin

Beilstein J. Org. Chem. 2017, 13, 639–643, doi:10.3762/bjoc.13.62

• structure to that of 1a,b. We can speculate that COOEt groups of 1l formed a chelate complex with ZnI2 and therefore strongly diminished its Lewis acidity, which is necessary for catalyst activation. All the compounds obtained were characterized by 1H and 13C NMR spectroscopy as well as high-resolution mass

• -spectrometry (for ethers, which are oils) or elemental analysis (for tosylamides, which are crystalline solids). The structures of the starting dienyne 1h and the cyclohexene trans-2b were established by X-ray crystallography. The structures of cis-2b and 3b had been reported previously [11][43]. Conclusion To

Structure–efficiency relationships of cyclodextrin scavengers in the hydrolytic degradation of organophosphorus compounds

• Sophie Letort,
• Michaël Bosco,
• Benedetta Cornelio,
• Frédérique Brégier,
• Sébastien Daulon,
• Géraldine Gouhier and
• François Estour

Beilstein J. Org. Chem. 2017, 13, 417–427, doi:10.3762/bjoc.13.45

• imidazole reduced the accessibility of substrates 11 and 12 to position 3. Thus, compounds 13 and 14 were isolated in comparable yields of 37% and 27%, respectively and this time without significantly different reactivities observed for the precursors 9 and 10. High resolution mass spectrometry (ESI+ HRMS

Decarboxylative and dehydrative coupling of dienoic acids and pentadienyl alcohols to form 1,3,6,8-tetraenes

• Ghina’a I. Abu Deiab,
• Mohammed H. Al-Huniti,
• I. F. Dempsey Hyatt,
• Emma E. Nagy,
• Kristen E. Gettys,
• Sommayah S. Sayed,
• Christine M. Joliat,
• Paige E. Daniel,
• Rupa M. Vummalaneni,
• Andrew T. Morehead Jr,
• Andrew L. Sargent and
• Mitchell P. Croatt

Beilstein J. Org. Chem. 2017, 13, 384–392, doi:10.3762/bjoc.13.41

• North Carolina Biotechnology Center (BRG-1205) and University of North Carolina at Greensboro is gratefully acknowledged. The authors thank Dr. Franklin J. Moy for assisting with analysis of NMR data and Dr. Daniel A. Todd for acquisition of the high resolution mass spectrometry data at the Triad Mass

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

• : 2.1 mm, particle size: 2.7 μm; Supelco) was used at a temperature of 40 °C. The capillary voltage was set to 3500 V and the capillary exit voltage was set according to the respective target mass. High-resolution mass spectrometry High-resolution ESI mass spectrometry was performed on a Waters QTof

Amidofluorene-appended lower rim 1,3-diconjugate of calix[4]arene: synthesis, characterization and highly selective sensor for Cu²⁺

• Rahman Hosseinzadeh,
• Mohammad Nemati,
• Reza Zadmard and
• Maryam Mohadjerani

Beilstein J. Org. Chem. 2016, 12, 1749–1757, doi:10.3762/bjoc.12.163

• -dicyclohexylcarbodiimide (DCC) in dichloromethane at room temperature gave the desired receptor L in 81% yield (Scheme 2). All the compounds including receptor L has been characterized by various spectral techniques such as 1H, 13C NMR and high resolution mass spectrometry (HRMS) (see Supporting Information File 1

Natural products from microbes associated with insects

• Christine Beemelmanns,
• Huijuan Guo,
• Maja Rischer and
• Michael Poulsen

Beilstein J. Org. Chem. 2016, 12, 314–327, doi:10.3762/bjoc.12.34

• the brood cell with the protective symbiont, beewolf females ensure that the larvae take up the symbionts from the surrounding soil while spinning the cocoon. Using high resolution mass spectrometry (HRMS) and nuclear magnetic resonance (NMR) spectroscopy, the protective secondary metabolites were

N-Methylphthalimide-substituted benzimidazolium salts and PEPPSI Pd–NHC complexes: synthesis, characterization and catalytic activity in carbon–carbon bond-forming reactions

• Senem Akkoç,
• Yetkin Gök,
• İlhan Özer İlhan and
• Veysel Kayser

Beilstein J. Org. Chem. 2016, 12, 81–88, doi:10.3762/bjoc.12.9

• for the ν(CN) bond of 1–4, respectively. Compounds 2 and 4 among these salts were further characterized by using high-resolution mass spectrometry (HRMS). The mass spectra demonstrated m/z peaks at 382.16 and 391.18 for the cationic moieties against the calculated value of m/z 382.43 and 391.44 for 2

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

• (e.g., pH fix at 7 for Cu2+ and pH fix at 3 for Ga3+). The isolated copper and gallium NOTA derivatives 12a,b were characterized by high-resolution mass spectrometry. Scope of the cycloaddition reaction Over the past decade, click chemistry has been applied to the synthesis of a wide variety of

Conformational equilibrium in supramolecular chemistry: Dibutyltriuret case

• Karina Mroczyńska,
• Małgorzata Kaczorowska,
• Erkki Kolehmainen,
• Ireneusz Grubecki,
• Marek Pietrzak and
• Borys Ośmiałowski

Beilstein J. Org. Chem. 2015, 11, 2105–2116, doi:10.3762/bjoc.11.227

• resolution mass spectrometry (HRMS) for the study of the association processes of 1 with benzoate 5 and naphthyridine 10 anions and to examine self-association of 1. The ESI–HRMS was previously successfully used for the study of complexation of triuret derivative with cations [44] and has been demonstrated

• complex. For detailed discussion that supports experimental findings refer to the computations section in Supporting Information File 1. Mass spectrometry To have a more complete view of properties of 1 we applied the combination of soft ionization technique electrospray ionization (ESI) with high

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

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

• temperature of 150 °C, the desired products were obtained in good yields (75–80%, Scheme 2). All structures of the benzo-fused tetrahydroquinazolines were characterized by 1H NMR and 13C-APT, infrared spectroscopy (FTIR) and high resolution mass spectrometry. Using compound 23 as an example, it can be

• 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

• mass spectrometry. The synthesis of compounds 14 [43] and 17 [44] has been previously reported in the literature. The structure of compound 18 was confirmed by X-ray diffraction analysis and Figure 2 shows the ORTEP diagram of this compound. The details of the crystal data and refinements are collected

New depsidones and isoindolinones from the mangrove endophytic fungus Meyerozyma guilliermondii (HZ-Y₂) isolated from the South China Sea

• Senhua Chen,
• Zhaoming Liu,
• Yayue Liu,
• Yongjun Lu,
• Lei He and
• Zhigang She

Beilstein J. Org. Chem. 2015, 11, 1187–1193, doi:10.3762/bjoc.11.133

• A and B (7 and 9), along with five known compounds were isolated from an endophytic fungus Meyerozyma guilliermondii, derived from the mangrove plant Kandelia obovata. Their structures were elucidated by 1D and 2D NMR spectroscopy and high resolution mass spectrometry (HREIMS). Compounds 1–6

New palladium–oxazoline complexes: Synthesis and evaluation of the optical properties and the catalytic power during the oxidation of textile dyes

• Rym Hassani,
• Mahjoub Jabli,
• Yakdhane Kacem,
• Jérôme Marrot,
• Damien Prim and
• Béchir Ben Hassine

Beilstein J. Org. Chem. 2015, 11, 1175–1186, doi:10.3762/bjoc.11.132

• reported in ppm relative to the residual solvent peak (7.27 ppm for CHCl3) for 1H spectra and (77.00 ppm for CDCl3) for 13C spectra. All chemical shifts were reported as δ values (ppm) relative to internal tetramethylsilane. High resolution mass spectrometry data were recorded on an Autospec Ultima (Waters

Thiazole-induced rigidification in substituted dithieno-tetrathiafulvalene: the effect of planarisation on charge transport properties

• Rupert G. D. Taylor,
• Joseph Cameron,
• Iain A. Wright,
• Neil Thomson,
• Olena Avramchenko,
• Alexander L. Kanibolotsky,
• Anto R. Inigo,
• Tell Tuttle and
• Peter J. Skabara

Beilstein J. Org. Chem. 2015, 11, 1148–1154, doi:10.3762/bjoc.11.129

• funding (EP/L012200/1). We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University for their high resolution mass spectrometry service.

Aspergiloid I, an unprecedented spirolactone norditerpenoid from the plant-derived endophytic fungus Aspergillus sp. YXf3

• Zhi Kai Guo,
• Rong Wang,
• Wei Huang,
• Xiao Nian Li,
• Rong Jiang,
• Ren Xiang Tan and
• Hui Ming Ge

Beilstein J. Org. Chem. 2014, 10, 2677–2682, doi:10.3762/bjoc.10.282

• chromatography (CC), octadecylsilyl (ODS) CC, Sephadex LH-20 and semi-preparative reversed-phase HPLC yielded 1 (4.3 mg). Aspergiloid I (1) was isolated as a colorless lamellar crystal, with the molecular formula C18H26O4 (6 double-bond equivalents) as derived from the ESI high-resolution mass spectrometry ([M

Oxidative phenylamination of 5-substituted 1-hydroxynaphthalenes to N-phenyl-1,4-naphthoquinone monoimines by air and light “on water”

• Julio Benites,
• Juan Meléndez,
• Cynthia Estela,
• David Ríos,
• Luis Espinoza,
• Iván Brito and
• Jaime A. Valderrama

Beilstein J. Org. Chem. 2014, 10, 2448–2452, doi:10.3762/bjoc.10.255

• NMR, 2D NMR) and high resolution mass spectrometry (HRMS). The position of the nitrogen substituent in these aminoquinones was determined by means of HMBC experiments. Encouraged by these results, the preparation of aminojuglones 4a and 4b was attempted by employing the hypothetical one pot procedure

Synthesis and solvodynamic diameter measurements of closely related mannodendrimers for the study of multivalent carbohydrate–protein interactions

• Yoann M. Chabre,
• Alex Papadopoulos,
• Alexandre A. Arnold and
• René Roy

Beilstein J. Org. Chem. 2014, 10, 1524–1535, doi:10.3762/bjoc.10.157

• those of the middle and internal regions. Interestingly, high resolution mass spectrometry (+TOF technique) resulted in the formation of multicharged adducts that matched the expected theoretical patterns, especially the one corresponding to [M + 7H]7+, as illustrated in Scheme 5 (insert). NMR diffusion

Magnesium bis(monoperoxyphthalate) hexahydrate as mild and efficient oxidant for the synthesis of selenones

• Andrea Temperini,
• Massimo Curini,
• Ornelio Rosati and
• Lucio Minuti

Beilstein J. Org. Chem. 2014, 10, 1267–1271, doi:10.3762/bjoc.10.127

• fully characterized by classical spectroscopic analysis and high resolution mass spectrometry. However, it is important to note that the oxidation of selenide 1b with MCPBA in methanol did not give selenone 2b but the corresponding methyl cyclopentyl ketone deriving from ring contraction [20]. On the

Tandem Cu-catalyzed ketenimine formation and intramolecular nucleophile capture: Synthesis of 1,2-dihydro-2-iminoquinolines from 1-(o-acetamidophenyl)propargyl alcohols

• Gadi Ranjith Kumar,
• Yalla Kiran Kumar,
• Ruchir Kant and
• Maddi Sridhar Reddy

Beilstein J. Org. Chem. 2014, 10, 1255–1260, doi:10.3762/bjoc.10.125

• %. Electron rich phenyl substrate 2l produced the corresponding product 9u in 65% yield while electron poor substrate 2m was found to be unreactive in the reaction. The structures of the products were confirmed by 1H NMR, 13C NMR and High Resolution Mass Spectrometry (HRMS). X-ray crystallography of one of

Cuevaenes C–E: Three new triene carboxylic derivatives from Streptomyces sp. LZ35ΔgdmAI

• Jing-Jing Deng,
• Chun-Hua Lu,
• Yao-Yao Li,
• Shan-Ren Li and
• Yue-Mao Shen

Beilstein J. Org. Chem. 2014, 10, 858–862, doi:10.3762/bjoc.10.82

• isomers – cuevaenes A (1) and C (3) as well as cuevaenes D (4) and E (5) – and cuevaene B (2) were isolated from gdmAI-disrupted Streptomyces sp. LZ35. The constitution of cuevaene C (3) was found to be identical to cuevaene A (1) by means of NMR spectroscopy and high resolution mass spectrometry. However

[²H₂₆]-1-epi-Cubenol, a completely deuterated natural product from Streptomyces griseus

• Christian A. Citron and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2013, 9, 2841–2845, doi:10.3762/bjoc.9.319

• /z = 119 to 130 points to eleven deuterium atoms. This in turn directly reveals the number of hydrogens in each of the fragment ions also for the unlabelled analyte, without the need for high resolution mass spectrometry (HRMS), similar to a recent report using 13C and 15N labellings for the