The digital code driven autonomous synthesis of ibuprofen automated in a 3D-printer-based robot

• Philip J. Kitson,
• Stefan Glatzel and
• Leroy Cronin

Beilstein J. Org. Chem. 2016, 12, 2776–2783, doi:10.3762/bjoc.12.276

• by the method described, opening possibilities for the sharing of validated synthetic ‘programs’ which can run on similar low cost, user-constructed robotic platforms towards an ‘open-source’ regime in the area of chemical synthesis. Keywords: 3D printing; digitising chemistry; ibuprofen; laboratory

• include the development of further open source solutions to allow robotic platforms to perform more of the routine functions of chemical synthesis such as work-up and purification routines. The widespread use of such low-cost automation of chemical synthesis could allow the development of an ‘open source

Green chemistry

• Luigi Vaccaro

Beilstein J. Org. Chem. 2016, 12, 2763–2765, doi:10.3762/bjoc.12.273

• examples of research platforms being independently developed, but all offer innovative tools for realizing chemically and environmentally efficient processes. Representative examples of these directions have been the subject of other excellent Thematic Series in the Beilstein Journal of Organic Chemistry

A self-assembled cyclodextrin nanocarrier for photoreactive squaraine

• Ulrike Kauscher and
• Bart Jan Ravoo

Beilstein J. Org. Chem. 2016, 12, 2535–2542, doi:10.3762/bjoc.12.248

• leads to aggregation and inactivation under physiological conditions, causing a reduced production of reactive oxygen species [26]. To overcome this drawback, we considered to immobilize the squaraines onto a platform that provides spatial separation (Figure 1). Our platforms of choice are vesicles self

Development of a continuous process for α-thio-β-chloroacrylamide synthesis with enhanced control of a cascade transformation

• Olga C. Dennehy,
• Valérie M. Y. Cacheux,
• Benjamin J. Deadman,
• Denis Lynch,
• Stuart G. Collins,
• Humphrey A. Moynihan and
• Anita R. Maguire

Beilstein J. Org. Chem. 2016, 12, 2511–2522, doi:10.3762/bjoc.12.246

• -chloroacrylamides, a class of highly versatile synthetic intermediates. Flow platforms to generate the α-chloroamide and α-thioamide precursors were successfully adopted, progressing from the previously employed batch chemistry, and in both instances afford a readily scalable methodology. The implementation of the

Ionic liquids as transesterification catalysts: applications for the synthesis of linear and cyclic organic carbonates

• Maurizio Selva,
• Alvise Perosa,
• Sandro Guidi and
• Lisa Cattelan

Beilstein J. Org. Chem. 2016, 12, 1911–1924, doi:10.3762/bjoc.12.181

• , P; n = 4, 6, 8, Ph), obtained by the methylation of trialkylphosphines or -amines with nontoxic DMC (Scheme 3, top) [34][35]. Such methyl carbonate onium salts are versatile platforms as they allow access to a number of ionic liquids via anion-metathesis reactions, which produce only CH3OH and CO2

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• to doing the occasional eccentric experiment. Building nanonoses As we were developing our delivery vehicle platforms, we were starting to think about sensing applications. One of the things that we observed in our protein binding work was that our nanoparticles had varying affinities for different

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

• efficient platforms for bidentate coordination in metal catalysis and good precursors of carboxylic acids, ketones and aldehydes upon oxidative cleavage of the keto/diol moiety [72]. More recently, a comprehensive study on the first evidence of the utility of these acceptors in organocatalysis has been

My maize and blue brick road to physical organic chemistry in materials

• Anne J. McNeil

Beilstein J. Org. Chem. 2016, 12, 229–238, doi:10.3762/bjoc.12.24

• were interested in applying our new gelators in sensing platforms. Because analyte-mediated sensors rely on a chemical transformation to take place prior to gel formation, the reaction rate should be fast, or ideally instantaneous. While most of our sensors were designed with this criterion in mind, we

Copper-catalyzed asymmetric conjugate addition of organometallic reagents to extended Michael acceptors

• Thibault E. Schmid,
• Sammy Drissi-Amraoui,
• Christophe Crévisy,
• Olivier Baslé and
• Marc Mauduit

Beilstein J. Org. Chem. 2015, 11, 2418–2434, doi:10.3762/bjoc.11.263

• ]. Unsymmetrical bidentate hydroxyalkyl precursor L12 led to the most efficient system in the insertion of methyl groups in such architectures, being highly versatile synthetic platforms [34][35]. A wide variety of α,β-unsaturated acyl-N-methylimidazoles could thus be reacted in high yields and

Biocatalysis for the application of CO₂ as a chemical feedstock

• Apostolos Alissandratos and
• Christopher J. Easton

Beilstein J. Org. Chem. 2015, 11, 2370–2387, doi:10.3762/bjoc.11.259

• fixation step, as well as subsequent transformations, must be harnessed efficiently. Suitable technological platforms are yet to be developed. Though there is much progress to be made before CO2 fixing enzymes may be readily used as modules in designer synthetic pathways, the rapid progress that is being

• made in the fields of genetic engineering, bioinformatics and synthetic biology, as well as renewable electricity generation and bioelectrochemical engineering hold much promise for the development of the biotechnological platforms that

Tuning the size of a redox-active tetrathiafulvalene-based self-assembled ring

• Sébastien Bivaud,
• Sébastien Goeb,
• Vincent Croué,
• Magali Allain,
• Flavia Pop and
• Marc Sallé

Beilstein J. Org. Chem. 2015, 11, 966–971, doi:10.3762/bjoc.11.108

• crystallographic data CCDC 1043205. Acknowledgements The authors gratefully acknowledge the CNRS, the Région des Pays de la Loire and the MENRT for PhD grants (SB and VC), the PIAM (Univ. Angers) and the CRMPO (Univ. Rennes) technical platforms for their assistance in spectroscopic analyses. An access to the

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

• tedious and multistep syntheses using either divergent or convergent approaches are arguably the reason for their limited use as support in organic synthesis [18]. To overcome these obstacles, a hybrid dendron-polymer might constitute a valuable alternative for high-loading platforms [19], despite the use

Synthesis of tripodal catecholates and their immobilization on zinc oxide nanoparticles

• Franziska Klitsche,
• Julian Ramcke,
• Julia Migenda,
• Andreas Hensel,
• Tobias Vossmeyer,
• Horst Weller,
• Silvia Gross and
• Wolfgang Maison

Beilstein J. Org. Chem. 2015, 11, 678–686, doi:10.3762/bjoc.11.77

• ] were converted to the corresponding triscatecholates 11 and 13 by coupling to dopamine (Scheme 2). The resulting triscatecholates 11 and 13 may be used as synthetically flexible platforms for functionalizations of surfaces via either nucleophilic addition (to the Michael acceptor in 11) or radical

• = hydroxybenzotriazole; TFA = trifluoroacetic acid, KOTMS = potassium trimethylsilanolate, DIEA = N,N-diisopropylethylamine. Synthesis of tripodal catecholate platforms 11 and 13 for surface functionalization. Supporting Information Supporting Information File 192: Experimental procedures, additional analytical data

Synthesis of divalent ligands of β-thio- and β-N-galactopyranosides and related lactosides and their evaluation as substrates and inhibitors of Trypanosoma cruzi trans-sialidase

• María Emilia Cano,
• Rosalía Agusti,
• Alejandro J. Cagnoni,
• María Florencia Tesoriero,
• José Kovensky,
• María Laura Uhrig and
• Rosa M. de Lederkremer

Beilstein J. Org. Chem. 2014, 10, 3073–3086, doi:10.3762/bjoc.10.324

• trans-sialidase. Taking into consideration that mainly ester but also glycosidic linkages are labile in biological fluids, we choose amide and thioglycosidic bonds to attach the sugar residues to the platforms. 2,3,4,6-Tetra-O-acetyl-β-D-galactosylamine (1) was obtained by catalytic hydrogenation of the

Photorelease of phosphates: Mild methods for protecting phosphate derivatives

• Sanjeewa N. Senadheera,
• Abraham L. Yousef and
• Richard S. Givens

Beilstein J. Org. Chem. 2014, 10, 2038–2054, doi:10.3762/bjoc.10.212

• does not occur in aqueous acetonitrile although diethyl phosphate is released. Other substitution patterns on the naphthyl or quinolin-5-yl core, such as the 2,6-naphthyl 10 or 8-benzyloxyquinolin-5-yl 24 platforms, also do not rearrange by aryl migration upon photolysis and, therefore, do not proceed

• application in biochemistry and chemistry [15]. We now report new pHP analogs with a fused aromatic or heteroaromatic extension of pHP. Our intent was to impose the pHP motif on the naphthyl and indolin-5-yl platforms (maintaining the critical substituent pattern) in order to foster aryl ketone migration by a

Orthogonal dual thiol–chloroacetyl and thiol–ene couplings for the sequential one-pot assembly of heteroglycoclusters

• Michele Fiore,
• Gour Chand Daskhan,
• Baptiste Thomas and
• Olivier Renaudet

Beilstein J. Org. Chem. 2014, 10, 1557–1563, doi:10.3762/bjoc.10.160

• binary combinations of α-D-Man or β-D-GlcNAc, thus providing rapid access to attractive heteroglycosylated platforms for diverse biological applications. Keywords: chemoselective ligation; heteroglycocluster; multivalency; multivalent glycosystems; one-pot synthesis; Introduction Multivalent

Multichromophoric sugar for fluorescence photoswitching

• Stéphane Maisonneuve,
• Rémi Métivier,
• Pei Yu,
• Keitaro Nakatani and
• Juan Xie

Beilstein J. Org. Chem. 2014, 10, 1471–1481, doi:10.3762/bjoc.10.151

• environmental saving reasons. Saccharides are polyfunctional molecules with well-defined stereogenic centres in one molecular unit, and constitute “platforms” on which multiple functional moieties can be attached. Among many applications, the use of photochemical devices based on sugar derivatives is

• "platforms". Experimental General details Commercially available solvents and reagents were used without further purification. Compounds 3 [27], 5 [25] and 9 [26] were prepared according to the literature. Melting points were measured on a Kofler bench. Optical rotations were measured using a JASCO P-2000

Synthesis of the first examples of iminosugar clusters based on cyclopeptoid cores

• Mathieu L. Lepage,
• Alessandra Meli,
• Anne Bodlenner,
• Céline Tarnus,
• Francesco De Riccardis,
• Irene Izzo and
• Philippe Compain

Beilstein J. Org. Chem. 2014, 10, 1406–1412, doi:10.3762/bjoc.10.144

• France, 103 Bd Saint-Michel, 75005 Paris, France 10.3762/bjoc.10.144 Abstract Cyclic N-propargyl α-peptoids of various sizes were prepared by way of macrocyclizations of linear N-substituted oligoglycines. These compounds were used as molecular platforms to synthesize a series of iminosugar clusters

• glycosidase inhibitor clusters published in the literature are based on these binding motifs [1][2][3][4][5][6][7][11][43] providing thus the opportunity to assess the relevance of cyclopeptoid cores by comparison with the other platforms already described. Scaffold synthesis The linear precursors of cyclic

Synthesis of a sucrose dimer with enone tether; a study on its functionalization

• Zbigniew Pakulski,
• Norbert Gajda,
• Magdalena Jawiczuk,
• Jadwiga Frelek,
• Piotr Cmoch and
• Sławomir Jarosz

Beilstein J. Org. Chem. 2014, 10, 1246–1254, doi:10.3762/bjoc.10.124

• synthesis; sucrose; Introduction Molecular recognition is one of the most important phenomena in stereoselective processes. Chiral crown ethers (or analogs) are particularly useful in enantioselective reactions [1][2] as well as differentiation of chiral guests [3][4]. From all of the chiral platforms

Plakilactones G and H from a marine sponge. Stereochemical determination of highly flexible systems by quantitative NMR-derived interproton distances combined with quantum mechanical calculations of ¹³C chemical shifts

• Simone Di Micco,
• Angela Zampella,
• Maria Valeria D’Auria,
• Carmen Festa,
• Simona De Marino,
• Raffaele Riccio,
• Craig P. Butts and
• Giuseppe Bifulco

Beilstein J. Org. Chem. 2013, 9, 2940–2949, doi:10.3762/bjoc.9.331

• support by the University of Salerno and by Ministero dell'Istruzione, dell'Università e della Ricerca (MIUR), PRIN 2009 “Design, conformational and configurational analysis of novel molecular platforms” is gratefully acknowledged.

Novel supramolecular affinity materials based on (−)-isosteviol as molecular templates

• Christina Lohoelter,
• Malte Brutschy,
• Daniel Lubczyk and
• Siegfried R. Waldvogel

Beilstein J. Org. Chem. 2013, 9, 2821–2833, doi:10.3762/bjoc.9.317

• -symmetric platforms hexahydroxytriphenylene and hexaaminotriptycene providing large and rigid molecular architectures. Because of the persistent cavities these scaffolds are very potent supramolecular affinity materials for head space analysis by quartz crystal microbalances. The scaffolds serve in

Investigating the continuous synthesis of a nicotinonitrile precursor to nevirapine

• Ashley R. Longstreet,
• Suzanne M. Opalka,
• Brian S. Campbell,
• B. Frank Gupton and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2013, 9, 2570–2578, doi:10.3762/bjoc.9.292

• [9][10][11][12]. This confluence of increased demand and cost provides an opportunity to reevaluate both the chemistry as well as the manufacturing platforms by which this drug can be produced. The two key Food and Drug Administration (FDA) registered starting materials in the commercial nevirapine

One-step synthesis of pyridines and dihydropyridines in a continuous flow microwave reactor

• Mark C. Bagley,
• Vincenzo Fusillo,
• Robert L. Jenkins,
• M. Caterina Lubinu and
• Christopher Mason

Beilstein J. Org. Chem. 2013, 9, 1957–1968, doi:10.3762/bjoc.9.232

• corresponding alcohol 7 [44], the transfer from batch reactor operation to continuous flow processing was efficient and required little further optimization. Furthermore, we showed that methodology developed using different reaction platforms, including commercial microreactors and stainless steel continuous

• provided a good comparison of different technology platforms. If the cyclodehydration could be incorporated into a multi-step process and was spontaneous under the reaction conditions, following Michael addition to ethynyl ketones, then the continuous production of pyridines from readily-available

• [67] and under microwave irradiation [10][68][69][70][71][72]. Furthermore, this reaction has been studied in a conductive heating Uniqsis FlowSyn reactor [71][73] and its comparison with microwave heating batch experiments showed that the energy efficiency of these technology platforms vary with

Synthesis of mucin-type O-glycan probes as aminopropyl glycosides

• David Benito-Alifonso,
• Rachel A. Jones,
• Anh-Tuan Tran,
• Hannah Woodward,
• Nichola Smith and
• M. Carmen Galan

Beilstein J. Org. Chem. 2013, 9, 1867–1872, doi:10.3762/bjoc.9.218

• ][11][12][13][14] than there are available for other types of glycosides and even fewer that lead to fragments ready to be conjugated to glycoarray platforms [15]. One of the most troublesome steps in previous approaches is the synthesis of the α-glycosidic linkage between 2-acetamido-2-deoxy-D

• -galactopyranose monosaccharide and the side-chain hydroxy groups. Herein we report a convergent approach for the highly efficient synthesis of mucin type O-glycan fragments 1–7 (Figure 1) containing an α-linked 3-aminopropyl-spacer ready for covalent attachment to glycoarray platforms. Results and Discussion A

• compounds 1–7 were produced functionalized with an amine linker ready to be incorporated onto glycoarray platforms for high throughput biological screening [31]. Structure of mucin-type oligosaccharide fragments synthesized. Synthesis of glycan targets 2–4. Synthesis of disaccharide targets 5 and 6

Hypervalent iodine/TEMPO-mediated oxidation in flow systems: a fast and efficient protocol for alcohol oxidation

• Nida Ambreen,
• Ravi Kumar and
• Thomas Wirth

Beilstein J. Org. Chem. 2013, 9, 1437–1442, doi:10.3762/bjoc.9.162

• platforms to perform reactions under continuous flow rather than in batch mode has led to improvements regarding safety and sustainability. Microreactor technology can be beneficial over classical approaches in a variety of chemical reactions. Many reactions can benefit from the properties of microreactors