Solvent-free and room temperature synthesis of 3-arylquinolines from different anilines and styrene oxide in the presence of Al₂O₃/MeSO₃H

• Hashem Sharghi,
• Mahdi Aberi,
• Mohsen Khataminejad and
• Pezhman Shiri

Beilstein J. Org. Chem. 2017, 13, 1977–1981, doi:10.3762/bjoc.13.193

• methanesulfonic acid 98% and acidic alumina (Al2O3) type 540 C were purchased from Fluka. The elemental analyses were performed with a Thermo Finnigan CHNS-O analyzer, 1112 series. The purity determination of the substrates and reaction monitoring were accomplished by TLC on silica gel PolyGram SILG/UV 254 plates

Mechanochemical synthesis of small organic molecules

• Tapas Kumar Achar,
• Anima Bose and
• Prasenjit Mal

Beilstein J. Org. Chem. 2017, 13, 1907–1931, doi:10.3762/bjoc.13.186

• under the LAG (liquid-assisted grinding) synthesis (Scheme 58) [190]. Initially, in situ monitoring of mechanochemical thiocarbamoylation suggests the formation of reactive intermediate which gradually disappears with the formation of thiocarbamoylated product. Furthermore isolation and spectroscopic

A novel application of 2-silylated 1,3-dithiolanes for the synthesis of aryl/hetaryl-substituted ethenes and dibenzofulvenes

• Grzegorz Mlostoń,
• Paulina Pipiak,
• Róża Hamera-Fałdyga and
• Heinz Heimgartner

Beilstein J. Org. Chem. 2017, 13, 1900–1906, doi:10.3762/bjoc.13.185

• with a FTIR NEXUS spectrometer (as film or KBr pellets). High resolution MS measurements were performed with a GCT Premier Waters instrument. Melting points were determined in capillaries with a Stuart SMP30 apparatus with automatic temperature monitoring. Microwave-supported syntheses of thioketones 1

Mechanochemical synthesis of thioureas, ureas and guanidines

• Vjekoslav Štrukil

Beilstein J. Org. Chem. 2017, 13, 1828–1849, doi:10.3762/bjoc.13.178

• Raman spectroscopy was devised [27]. Finally, these two in situ techniques have been successfully merged to allow simultaneous monitoring of mechanochemical reactions by PXRD and Raman spectroscopy [28][29]. Review Mechanochemical synthesis of (thio)ureas Thioureas In a paper by Kaupp et al. a study on

• nucleophilic aromatic substrates with bis(1-benzotriazolyl)methanethione (26) under ball-milling conditions (Scheme 9) [41]. The application of in situ Raman spectroscopy monitoring of mechanochemical reactions, in combination with solid-state characterization through FTIR-ATR, PXRD and ssNMR analyses

• almost quantitative yields. The in situ Raman monitoring of a 1:2 mixture of 26 and 4-bromoaniline, which results in the formation of symmetrical bis(4-bromophenyl)thiourea 28d revealed thiocarbamoyl benzotriazole 27d as the reactive intermediate (Figure 4). Starting from 27a or 29, bis-thiourea 22a can

Mechanochemical N-alkylation of imides

• Anamarija Briš,
• Mateja Đud and
• Davor Margetić

Beilstein J. Org. Chem. 2017, 13, 1745–1752, doi:10.3762/bjoc.13.169

• organic solvents. Ex situ IR spectroscopy (ATR) of milling of imides 11–17 with K2CO3 was used for monitoring the reaction progress, which showed for instance, that potassium phthalimide [29] was formed after one hour of grinding (Figure 2). This salt was, without isolation, subjected to further milling

• with benzyl bromide with LAG (DMF) to obtain alkylated products in high yields. Formation of potassium salts of other imides listed in Table 3 by K2CO3 has been also proven by ex situ IR monitoring (see Supporting Information File 1). It indicates that potassium carbonate is capable of the

Mechanochemical borylation of aryldiazonium salts; merging light and ball milling

• José G. Hernández

Beilstein J. Org. Chem. 2017, 13, 1463–1469, doi:10.3762/bjoc.13.144

• experiments, milling of the reactants and PC was carried out for a time in the range of 15 min to 2 h. The analysis of the composition of the reaction mixture showed significant formation of the product after 30 min of milling/irradiation (Table 1, entry 6). Monitoring the progress of a mixture of the

An improved preparation of phorbol from croton oil

• Alberto Pagani,
• Simone Gaeta,
• Andrei I. Savchenko,
• Craig M. Williams and
• Giovanni Appendino

Beilstein J. Org. Chem. 2017, 13, 1361–1367, doi:10.3762/bjoc.13.133

• methylate solution was necessary to reach and stabilize this pH value, and during the addition the amber color of the oil initially faded, and next darkened to eventually become black when the pH was strongly basic (>10). The course of the transesterification was followed by TLC, monitoring the appearance

Detection of therapeutic radiation in three-dimensions

• John A. Adamovics

Beilstein J. Org. Chem. 2017, 13, 1325–1331, doi:10.3762/bjoc.13.129

• conveniently achieved by monitoring the 1H NMR spectra, in which the representative CHO proton singlet of the starting aryl aldehyde (ca. 11 ppm) diminishes as the characteristic singlet of the methine DTM product (ca. 5.5 ppm) grows during the course of the reaction. The conformational structure of a DTM has

Synthesis of alkynyl-substituted camphor derivatives and their use in the preparation of paclitaxel-related compounds

• M. Fernanda N. N. Carvalho,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2017, 13, 1230–1238, doi:10.3762/bjoc.13.122

• of the alkynyllithium compound are necessary because the first one is required for the deprotonation of the relatively acidic proton at the sulfonamide nitrogen. Compounds 21a and 21b were then reacted with 5 mol % PtCl2(PhCN)2 at 60 °C in CHCl3 [42]. For 1H NMR monitoring, the same conditions were

A concise and practical stereoselective synthesis of ipragliflozin L-proline

• Shuai Ma,
• Zhenren Liu,
• Jing Pan,
• Shunli Zhang and
• Weicheng Zhou

Beilstein J. Org. Chem. 2017, 13, 1064–1070, doi:10.3762/bjoc.13.105

• served as the references both in the monitoring the reaction and the quality control of the drug. Experimental All solvents and reagents were of reagent grade and used without further purification. HPLC analyses were recorded using a Waters Arc HPLC System with 2998 PDA Detector or an Agilent 1260 HPLC

Synthesis and enzymatic ketonization of the 5-(halo)-2-hydroxymuconates and 5-(halo)-2-hydroxy-2,4-pentadienoates

• Tyler M. M. Stack,
• William H. Johnson Jr. and
• Christian P. Whitman

Beilstein J. Org. Chem. 2017, 13, 1022–1031, doi:10.3762/bjoc.13.101

• equation. In the first 5 s of the reaction, the absorbance at 232 nm was still decreasing. Kinetic parameters were determined as described above. The Lc 4-OT conversion of 5a–c to the respective α,β-unsaturated ketones 9a–c was compared to the Pp 4-OT-catalyzed conversion by monitoring the spectral changes

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

• The implementation of automation in the multistep flow synthesis is essential for transforming laboratory-scale chemistry into a reliable industrial process. In this review, we briefly introduce the role of automation based on its application in synthesis viz. auto sampling and inline monitoring

• scale of operation. This classification will cover the broader range in the multistep synthesis literature. Keywords: automation; control strategy; flow chemistry; in-line monitoring; multistep synthesis optimization; Introduction Multistep flow synthesis In the recent time the concept of flow

• categorized into three levels. Each level or component of automation has a very different objective, complexity, and relevance to synthesis. I) Auto-sampling and analysis: In such cases, there is no control structure or Design of Experiment (DoE). Here automation is responsible for in-line monitoring of

Use of costic acid, a natural extract from Dittrichia viscosa, for the control of Varroa destructor, a parasite of the European honey bee

• Kalliopi Sofou,
• Demosthenis Isaakidis,
• Apostolos Spyros,
• Anita Büttner,
• Athanassios Giannis and
• Haralambos E. Katerinopoulos

Beilstein J. Org. Chem. 2017, 13, 952–959, doi:10.3762/bjoc.13.96

• important pollinators of crop monocultures worldwide [5]. A recent article on the protection of pollinators stresses the need for “statistically robust monitoring programs for native bees”, especially when taking into account that some species have been designated as endangered [6]. In times when the global

Synthesis of D-manno-heptulose via a cascade aldol/hemiketalization reaction

• Yan Chen,
• Xiaoman Wang,
• Junchang Wang and
• You Yang

Beilstein J. Org. Chem. 2017, 13, 795–799, doi:10.3762/bjoc.13.79

• on TLC monitoring. Given that the C4 aldehyde 3 was unstable upon purification by silica gel column chromatography, it was immediately used for the subsequent coupling after the extraction procedure. The aldol reaction of aldehyde 3 with the readily available ketone 4 [42][43] under the catalysis of

Fluorescent carbon dots from mono- and polysaccharides: synthesis, properties and applications

• Stephen Hill and
• M. Carmen Galan

Beilstein J. Org. Chem. 2017, 13, 675–693, doi:10.3762/bjoc.13.67

• the ionisation of the surface functionality (Scheme 8). The feature is reversible as demonstrated by monitoring the PL intensity at a given excitation at different pHs and during several iterations. Similarly the CDs were shown to have an emission-intensity dependence on the temperature. Upon

Novel β-cyclodextrin–eosin conjugates

• Gábor Benkovics,
• Damien Afonso,
• András Darcsi,
• Szabolcs Béni,
• Sabrina Conoci,
• Éva Fenyvesi,
• Lajos Szente,
• Milo Malanga and
• Salvatore Sortino

Beilstein J. Org. Chem. 2017, 13, 543–551, doi:10.3762/bjoc.13.52

• oxygen. Although several indirect methodologies based on suitable chemical traps are well known to detect 1O2 formation, the best experimental method to prove and quantify its production is its direct detection. It is based on the monitoring of the typical phosphorescence of 1O2 in the near-IR spectral

Contribution of microreactor technology and flow chemistry to the development of green and sustainable synthesis

• Flavio Fanelli,
• Giovanna Parisi,
• Leonardo Degennaro and
• Renzo Luisi

Beilstein J. Org. Chem. 2017, 13, 520–542, doi:10.3762/bjoc.13.51

• probe, for monitoring the transformation, and an in line liquid–liquid separator to avoid tedious work-up procedures, thus saving solvents, resources and optimizing work times. This system was demonstrated to work for 11 h with higher conversion and enantioselectivity (er >99.9%) in comparison to the

• very compact in size [1.0 m × 0.7 m × 1.8 m, (W × L × H)], and low-weighing (about 100 kg) and was able to perform complex multistep synthesis, work-up procedures as well as purification operations such as crystallization. This platform was also equipped with devices for real-time monitoring and final

Adsorption of RNA on mineral surfaces and mineral precipitates

• Elisa Biondi,
• Yoshihiro Furukawa,
• Jun Kawai and
• Steven A. Benner

Beilstein J. Org. Chem. 2017, 13, 393–404, doi:10.3762/bjoc.13.42

• , while samples that were unstained (white) remained such for the duration of the monitoring period. Temperature stability of RNA adsorbed onto aragonite surfaces For these experiments, five small clusters of aragonite were obtained from an original crystal cluster with the use of a hammer. These were

Polyketide stereocontrol: a study in chemical biology

• Kira J. Weissman

Beilstein J. Org. Chem. 2017, 13, 348–371, doi:10.3762/bjoc.13.39

• to yield the L-methyl. In mechanistic terms, epimerization involves removal of the C-2 proton and delivery of proton to C-2 from the opposite face of the resulting, planar enol/enolate intermediate. Monitoring by NMR of the rate of epimerization of a model C-3-ketoacyl ester (ethyl 2

NMR reaction monitoring in flow synthesis

• M. Victoria Gomez and
• Antonio de la Hoz

Beilstein J. Org. Chem. 2017, 13, 285–300, doi:10.3762/bjoc.13.31

• reviewed. Some recent selected applications have been collected, including synthetic applications, the determination of the kinetic and thermodynamic parameters and reaction optimization, even in single experiments and on the μL scale. Finally, software that allows automatic reaction monitoring and

• Kentgens et al. [22]. Applications of flow NMR in reaction monitoring Keifer defined flow-NMR [28] as any NMR technique in which the sample flows through a tube into the NMR probe at some time during the measurement process. The first reported use of a flow-NMR technique was in 1951 [29], when the 1H

• will discuss some recent selected examples of the application of NMR reaction monitoring in flow chemistry. These examples include the design of flow systems, the use of standard NMR instruments and flow probes, the use of microcoils and finally the use of flow-NMR for kinetic and mechanistic studies

Spectral and DFT studies of anion bound organic receptors: Time dependent studies and logic gate applications

• Srikala Pangannaya,
• Neethu Padinchare Purayil,
• Shweta Dabhi,
• Venu Mankad,
• Prafulla K. Jha,
• Satyam Shinde and
• Darshak R. Trivedi

Beilstein J. Org. Chem. 2017, 13, 222–238, doi:10.3762/bjoc.13.25

• presence of the anion. The time response for AcO− ion monitoring the band at 492 nm and 560 nm for R1 and R2, respectively, is shown in Figure 13 and Figure 14. The rate constants calculated for the band at 395 (R1) and 492 (R1 + AcO−); 459 nm (R2) and 560 nm (R2 + AcO−) are too close indicating the

3D printed fluidics with embedded analytic functionality for automated reaction optimisation

• Andrew J. Capel,
• Andrew Wright,
• Matthew J. Harding,
• George W. Weaver,
• Yuqi Li,
• Russell A. Harris,
• Steve Edmondson,
• Ruth D. Goodridge and
• Steven D. R. Christie

Beilstein J. Org. Chem. 2017, 13, 111–119, doi:10.3762/bjoc.13.14

• micro- and milliscale fluidic devices. When coupled with online monitoring and optimisation software, this offers an advanced, customised method for performing automated chemical synthesis. This paper reports the use of two additive manufacturing processes, stereolithography and selective laser melting

• , to create multifunctional fluidic devices with embedded reaction monitoring capability. The selectively laser melted parts are the first published examples of multifunctional 3D printed metal fluidic devices. These devices allow high temperature and pressure chemistry to be performed in solvent

Extrusion – back to the future: Using an established technique to reform automated chemical synthesis

• Deborah E. Crawford

Beilstein J. Org. Chem. 2017, 13, 65–75, doi:10.3762/bjoc.13.9

• literature demonstrating the utilisation of near-infrared spectroscopy for online monitoring to determine where in the extruder the cocrystal begins to form. Consequently this also provides feedback regarding screw configuration and deductions can be made as to whether sufficient mechanical energy is being

Versatile synthesis of end-reactive polyrotaxanes applicable to fabrication of supramolecular biomaterials

• Atsushi Tamura,
• Asato Tonegawa,
• Yoshinori Arisaka and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2016, 12, 2883–2892, doi:10.3762/bjoc.12.287

• 7 could be utilized for monitoring the intracellular internalization of the PRXs, the intracellular uptake of 7 was investigated. HeLa cells were treated with 7 for 26 h, before observation by confocal laser scanning microscopy (CLSM) (Figure 5). The punctate 7 is clearly observed at the perinuclear

Biochemical and structural characterisation of the second oxidative crosslinking step during the biosynthesis of the glycopeptide antibiotic A47934

• Veronika Ulrich,
• Clara Brieke and
• Max J. Cryle

Beilstein J. Org. Chem. 2016, 12, 2849–2864, doi:10.3762/bjoc.12.284

• ion monitoring (SIM) mode. (a) StaF activity against different peptide substrates and using NRPS constructs; the activity of StaF with Tei7-L-Hpg7 (magenta), Tei7-D-Hpg7 (green), Pek7-rac-Hpg7 (orange) and Act7-rac-Hpg7 (blue) were determined; all peptides were bound to wildtype and hybrid PCP-X