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Search for "azide–alkyne" in Full Text gives 131 result(s) in Beilstein Journal of Organic Chemistry.

Mechanochemistry of nucleosides, nucleotides and related materials

  • Olga Eguaogie,
  • Joseph S. Vyle,
  • Patrick F. Conlon,
  • Manuela A. Gîlea and
  • Yipei Liang

Beilstein J. Org. Chem. 2018, 14, 955–970, doi:10.3762/bjoc.14.81

Graphical Abstract
  • (Scheme 5) [42]. In the absence of light, azobenzene derivatives were isolated as the pure E-isomers. In their original report, Sharpless and co-workers described the use of copper turnings to promote a regioselective azidealkyne [3 + 2]-cycloaddition ("click") reaction over 24 hours [43]. High-speed
  • and carboxylic acid Boc protection using an improvised attritor-type mill. Nucleobase Boc protection via transient silylation using an improvised attritor-type mill. Chemoselective N-acylation of an aminonucleoside using LAG in a MBM. Azidealkyne cycloaddition reactions performed in a copper vessel
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Published 27 Apr 2018

Sequential Ugi reaction/base-induced ring closing/IAAC protocol toward triazolobenzodiazepine-fused diketopiperazines and hydantoins

  • Robby Vroemans,
  • Fante Bamba,
  • Jonas Winters,
  • Joice Thomas,
  • Jeroen Jacobs,
  • Luc Van Meervelt,
  • Jubi John and
  • Wim Dehaen

Beilstein J. Org. Chem. 2018, 14, 626–633, doi:10.3762/bjoc.14.49

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  • together all necessary functionalities for further transformations. The Ugi adducts were then subjected to a base-induced ring closing and an intramolecular azidealkyne cycloaddition reaction in succession to obtain highly fused benzodiazepine frameworks. Keywords: benzodiazepine; 2,5-diketopiperazine
  • ; hydantoin; intramolecular azidealkyne cycloaddition; Ugi reaction; Introduction The versatile bioactivities of multiring-fused heterocyclic scaffolds continue to attract significant attention in developing new methods for their synthesis. A plethora of functionalized fused heterocycles can be easily
  • multicomponent reactions with intramolecular azidealkyne cycloaddition (IAAC) for the generation of triazole-fused heterocycles [12][13][14][15][16][17][18][19][20][21][22][23]. In this report we disclose our results on the development of a sequential synthetic approach involving Ugi 4-component reaction (4-CR
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Published 14 Mar 2018

Synthesis and biological evaluation of RGD and isoDGR peptidomimetic-α-amanitin conjugates for tumor-targeting

  • Lizeth Bodero,
  • Paula López Rivas,
  • Barbara Korsak,
  • Torsten Hechler,
  • Andreas Pahl,
  • Christoph Müller,
  • Daniela Arosio,
  • Luca Pignataro,
  • Cesare Gennari and
  • Umberto Piarulli

Beilstein J. Org. Chem. 2018, 14, 407–415, doi:10.3762/bjoc.14.29

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  • disulfide linker in the cytoplasm. In another example, Perrin and co-workers conjugated the N-propargylasparagine of an amanitin analog to a cycloRGD integrin ligand (cyclo[RGDfK]) using a copper-catalyzed azidealkyne cycloaddition [8]. The conjugates were tested in the U87 glioblastoma cell line, but only
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Published 14 Feb 2018

Recent applications of click chemistry for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles

  • Vivek Poonthiyil,
  • Thisbe K. Lindhorst,
  • Vladimir B. Golovko and
  • Antony J. Fairbanks

Beilstein J. Org. Chem. 2018, 14, 11–24, doi:10.3762/bjoc.14.2

Graphical Abstract
  • glycoscience. In this review we present recent advances made in the use of one type of click chemistry, namely the azidealkyne Huisgen cycloaddition, for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles. Keywords: azidealkyne Huisgen cycloaddition; carbohydrates
  • synthesis and application of GAuNPs can be found in the reviews by Penadés and co-workers [9][26] and also in a recent review by Compostella et al. [10]. In this regard, azidealkyne click chemistry is an attractive approach that could be used to synthesize GAuNPs. The functionalization of AuNPs using the
  • azidealkyne Huisgen cycloaddition AuNP surface modification using NCAAC The azidealkyne Huisgen cycloaddition (AAC) is a 1,3-dipolar cycloaddition between an organic azide and an alkyne that gives triazole products [37][38]. The non-catalysed azidealkyne Huisgen cycloaddition (NCAAC) is very slow
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Published 03 Jan 2018

Synthetic mRNA capping

  • Fabian Muttach,
  • Nils Muthmann and
  • Andrea Rentmeister

Beilstein J. Org. Chem. 2017, 13, 2819–2832, doi:10.3762/bjoc.13.274

Graphical Abstract
  • ) followed by treatment with aqueous ammonia (rt, 3 h). Click chemistry for the preparation of capped RNA and cap analogues. (A) Preparation of capped RNA via a copper-catalyzed azidealkyne cycloaddition (CuAAC) of an azido-modified cap analogue with a 5'-alkyne bearing RNA [120]. (B) An alkyne-modified
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Published 20 Dec 2017

Asymmetric synthesis of propargylamines as amino acid surrogates in peptidomimetics

  • Matthias Wünsch,
  • David Schröder,
  • Tanja Fröhr,
  • Lisa Teichmann,
  • Sebastian Hedwig,
  • Nils Janson,
  • Clara Belu,
  • Jasmin Simon,
  • Shari Heidemeyer,
  • Philipp Holtkamp,
  • Jens Rudlof,
  • Lennard Klemme,
  • Alessa Hinzmann,
  • Beate Neumann,
  • Hans-Georg Stammler and
  • Norbert Sewald

Beilstein J. Org. Chem. 2017, 13, 2428–2441, doi:10.3762/bjoc.13.240

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  • intriguing versatility as building blocks in organic and medicinal chemistry, as their reactivity is unique. Their chemistry involves several highly selective reactions, e.g., [3 + 2] cycloadditions with azides and isoelectronic functional groups (among them the copper or ruthenium-catalyzed azidealkyne
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Published 15 Nov 2017

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

  • Martina Tireli,
  • Silvija Maračić,
  • Stipe Lukin,
  • Marina Juribašić Kulcsár,
  • Dijana Žilić,
  • Mario Cetina,
  • Ivan Halasz,
  • Silvana Raić-Malić and
  • Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

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  • spin resonance (ESR) spectroscopy; in situ Raman monitoring; mechanochemistry; quinoline; solid-state click chemistry; Introduction The copper-catalyzed azidealkyne cycloaddition (CuAAC) represents a prime example of click chemistry. Click chemistry describes “a set of near-perfect” reactions [1] for
  • bond bioisosteres made the click reaction a valuable synthetic methodology for conjugation of bioactive molecules [7][8][9] aiming to improve their biological activities [4][10][11]. Discovery of copper(I) ion catalysis in azidealkyne cycloadditions was decisive for applications of this reaction, as
  • it increases reaction rates and yields and directs the azidealkyne cycloaddition exclusively towards 1,4-substituted regioisomers, whereas the non-catalyzed process results in a non-stoichiometric mixture of 1,4- and 1,5-regioisomers. Even though CuAAC reactions are efficiently performed in solution
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Published 06 Nov 2017

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

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Published 11 Aug 2017

An eco-compatible strategy for the diversity-oriented synthesis of macrocycles exploiting carbohydrate-derived building blocks

  • Sushil K. Maurya and
  • Rohit Rana

Beilstein J. Org. Chem. 2017, 13, 1106–1118, doi:10.3762/bjoc.13.110

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  • the iterative use of readily available sugar-derived alkyne/azide–alkene building blocks coupled through copper catalyzed azidealkyne cycloaddition (CuAAC) reaction followed by pairing of the linear cyclo-adduct using greener reaction conditions. The eco-compatibility, mild reaction conditions
  • the synthesis. The cyclization of the linear precursor is usually achieved by utilizing various ring-closing reactions such as Diels–Alder reactions, [15] aldol reactions, [16] copper-catalyzed azidealkyne cycloaddition, [17][18] macrolactonization, macrolactamizations, Staudinger ligation or
  • ] glycosides and macrocyclic glycolipids [11]. Similarly, the copper-catalyzed azidealkyne cycloaddition (CuAAC) reaction has found wide application in medicinal chemistry [33], biology [34][35], polymer chemistry [36], carbohydrates [37][38][39][40], peptides [41][42][43][44] and in materials science [45][46
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Published 09 Jun 2017

Glyco-gold nanoparticles: synthesis and applications

  • Federica Compostella,
  • Olimpia Pitirollo,
  • Alessandro Silvestri and
  • Laura Polito

Beilstein J. Org. Chem. 2017, 13, 1008–1021, doi:10.3762/bjoc.13.100

Graphical Abstract
  • peanut agglutinin [25]. In this case, the glycosyl residue is not coated on the gold surface by means of a thiol moiety but exploiting the strain-promoted azidealkyne cycloaddition (SPAAC) to covalently link an azido galactoside on a lipid cyclooctyne. In this manner, the amphiphilic glyco-lipid can be
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Published 24 May 2017

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

Graphical Abstract
  • the multistep synthesis of rufinamide, an antiepileptic agent [14] (Scheme 3). The process involves three steps namely azide synthesis, amide synthesis and click reaction or azidealkyne cycloaddition. For the azide synthesis, the aryl bromide (1 equiv) and sodium azide (1.3 equiv) are reacted in a
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Published 19 May 2017

Interactions between shape-persistent macromolecules as probed by AFM

  • Johanna Blass,
  • Jessica Brunke,
  • Franziska Emmerich,
  • Cédric Przybylski,
  • Vasil M. Garamus,
  • Artem Feoktystov,
  • Roland Bennewitz,
  • Gerhard Wenz and
  • Marcel Albrecht

Beilstein J. Org. Chem. 2017, 13, 938–951, doi:10.3762/bjoc.13.95

Graphical Abstract
  • , synthesized from polymer 8 (Scheme 3) through Cu(I)-catalyzed azidealkyne cycloaddition (CuAAC) with the triethylene glycol linker 11 (N3-TEG-NH2) which had been prepared in a five-step procedure [62][63]. Probing multivalent interactions by AFM The adhesive forces of 12, due to supramolecular interactions
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Published 18 May 2017

Energy down converting organic fluorophore functionalized mesoporous silica hybrids for monolith-coated light emitting diodes

  • Markus Börgardts and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2017, 13, 768–778, doi:10.3762/bjoc.13.76

Graphical Abstract
  • functionalization can be achieved upon ligating a triethylsiloxy-functionalized azide and a terminal alkynyl-functionalized luminophore by CuAAC (Cu-catalyzed azidealkyne cycloaddition) [21][22][23]. Commencing from a 2-hydroxy-substituted Nile red 1 or 3-hydroxymethylperylene (2) the alkyne-substituted
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Published 25 Apr 2017

Fast and efficient synthesis of microporous polymer nanomembranes via light-induced click reaction

  • Qi An,
  • Youssef Hassan,
  • Xiaotong Yan,
  • Peter Krolla-Sidenstein,
  • Tawheed Mohammed,
  • Mathias Lang,
  • Stefan Bräse and
  • Manuel Tsotsalas

Beilstein J. Org. Chem. 2017, 13, 558–563, doi:10.3762/bjoc.13.54

Graphical Abstract
  • solid liquid interfacial layer-by-layer (LbL) synthesis of CMP-nanomembranes via Cu catalyzed azidealkyne cycloaddition (CuAAC). However, this process featured very long reaction times and limited scalability. Herein we present the synthesis of surface grown CMP thin films and nanomembranes via light
  • catalyzed azidealkyne cycloaddition (CuAAC) approach, respectively [16]. These procedures are still limited to conductive substrates or associated with long reaction times. In this work, we present a novel strategy for the LbL synthesis of CMP thin films and nanomembranes, using the light-induced and
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Published 17 Mar 2017

Investigation of the action of poly(ADP-ribose)-synthesising enzymes on NAD+ analogues

  • Sarah Wallrodt,
  • Edward L. Simpson and
  • Andreas Marx

Beilstein J. Org. Chem. 2017, 13, 495–501, doi:10.3762/bjoc.13.49

Graphical Abstract
  • introducing small, terminal alkyne functionalities at common sites of the adenine base. Upon successful incorporation into PAR, these alkynes serve as handles for copper(I) catalysed azidealkyne click reaction (CuAAC) [22] with fluorescent dyes. Terminal alkynes are the smallest possible reporter group that
  • + analogue or a 1:1 mixture. Then, copper(I)-catalysed azidealkyne click reaction (CuAAC) is performed and mixture is resolved by SDS PAGE. SDS PAGE analysis of ADP-ribosylation of histone H1.2 with ARTD1, ARTD2, ARTD5 and ARTD6 using NAD+ analogue 1. Upper panel shows Coomassie Blue staining; lower panel
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Published 10 Mar 2017

Solid-phase enrichment and analysis of electrophilic natural products

  • Frank Wesche,
  • Yue He and
  • Helge B. Bode

Beilstein J. Org. Chem. 2017, 13, 405–409, doi:10.3762/bjoc.13.43

Graphical Abstract
  • ). Furthermore, the molecular formula of the cleaved azidealkyne cycloaddition product 3 was confirmed by HPLC–HRMS (calcd mass: m/z 567.2636 [M + H]+, found: m/z 567.2635 [M + H]+, Δppm = 0.1). Compound 1 could hardly be detected in extracts from standard growth media but was detected from infected insects and
  • dinitrogen (−28) as characteristic fragments for CARR adducts. Principle of azidation of XAD extracts from P. luminescens TT01 containing 1 and subsequent azide enrichment with CARR (2). After the vicinal azido alcohol is covalently bound to the resin through an azidealkyne cycloaddition, compound 3 is
  • tested strains, calculated molecular formulas of possible azidealkyne cycloaddition products, and the molecular formulas of the putative parent compounds derived from subtraction of the azide and CARR-derived moiety (C13H19N4O2S). Supporting Information Supporting Information File 30: Materials
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Published 02 Mar 2017

Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

  • Michal Medvecký,
  • Igor Linder,
  • Luise Schefzig,
  • Hans-Ulrich Reissig and
  • Reinhold Zimmer

Beilstein J. Org. Chem. 2016, 12, 2898–2905, doi:10.3762/bjoc.12.289

Graphical Abstract
  • -oxazines bearing the newly installed alkynyl group at C-5 are ideal candidates for efficient subsequent transformations. A very popular and widely applied reaction of terminal alkynes is the copper-catalyzed azidealkyne cycloaddition, also termed as click reaction, efficiently leading to 1,4-disubstituted
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Published 29 Dec 2016

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

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  • methods of introducing functional groups at the threading CD moieties of PRXs are used. Among the various chemical modifications, the introduction of azide or alkynyl groups at the threading CDs of the PRX is particularly attractive, because these functional groups undergo efficient azidealkyne Huisgen
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Published 28 Dec 2016

A versatile route to polythiophenes with functional pendant groups using alkyne chemistry

  • Xiao Huang,
  • Li Yang,
  • Rikard Emanuelsson,
  • Jonas Bergquist,
  • Maria Strømme,
  • Martin Sjödin and
  • Adolf Gogoll

Beilstein J. Org. Chem. 2016, 12, 2682–2688, doi:10.3762/bjoc.12.265

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  • of such functionalization using a Sonogashira cross-coupling [26] and an azidealkyne Huisgen cycloaddition [27]. One of the advantages of the cross-coupling and click chemistry is that it allows for reaction conditions tolerant for nearly all of the above mentioned functional groups. Additionally
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Published 09 Dec 2016

Synthesis, dynamic NMR characterization and XRD studies of novel N,N’-substituted piperazines for bioorthogonal labeling

  • Constantin Mamat,
  • Marc Pretze,
  • Matthew Gott and
  • Martin Köckerling

Beilstein J. Org. Chem. 2016, 12, 2478–2489, doi:10.3762/bjoc.12.242

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  • connection to the label (e.g., fluorescence dye, radionuclide) and the second is used for the introduction of a (bioorthogonal) functional group (e.g., azide, alkyne, phosphane, tetrazine) to later connect to the biomolecule via bioorthogonal ligation. Our aim was the development of novel, N,N
  • to demonstrate the Cu-catalyzed azidealkyne click reaction (Huisgen 1,3-dipolar cycloaddition) and the traceless Staudinger ligation, a proof of concept study was performed for the site-selective labeling of a pharmacologically active peptide and a small organic compound. These compounds provide the
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Published 21 Nov 2016

Construction of bis-, tris- and tetrahydrazones by addition of azoalkenes to amines and ammonia

  • Artem N. Semakin,
  • Aleksandr O. Kokuev,
  • Yulia V. Nelyubina,
  • Alexey Yu. Sukhorukov,
  • Petr A. Zhmurov,
  • Sema L. Ioffe and
  • Vladimir A. Tartakovsky

Beilstein J. Org. Chem. 2016, 12, 2471–2477, doi:10.3762/bjoc.12.241

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  • 1 to ammonia (Table 2) have a special significance because the expected trishydrazones 11 are obvious analogs of tris(iminomethyl)amines widely used in the catalysis of azidealkyne cycloadditions [29][30][31][32][34]. Furthermore, intramolecular cyclotrimerization of C=N bonds in trishydrozones
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Published 21 Nov 2016

Dinuclear thiazolylidene copper complex as highly active catalyst for azid–alkyne cycloadditions

  • Anne L. Schöffler,
  • Ata Makarem,
  • Frank Rominger and
  • Bernd F. Straub

Beilstein J. Org. Chem. 2016, 12, 1566–1572, doi:10.3762/bjoc.12.151

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  • Anne L. Schoffler Ata Makarem Frank Rominger Bernd F. Straub Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany 10.3762/bjoc.12.151 Abstract A dinuclear N-heterocyclic carbene (NHC) copper complex efficiently catalyzes azidealkyne
  • -heterocyclic carbene, linker, sacrificial ligand, and counter ion. Keywords: catalysis; click; copper; CuAAC; N-heterocyclic carbene; thiazole; Introduction The copper-catalyzed azidealkyne cycloaddition (CuAAC) is one of the most important “click” reactions for the facile covalent linking of two molecules
  • [1][2][3]. In 2002, the research groups of Meldal and Sharpless independently discovered the strongly rate-enhancing effect of copper(I) salts for azidealkyne cycloadditions. The 1,4-disubstituted 1,2,3-triazoles are formed exclusively with essentially quantitative conversion and under mild reaction
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Published 21 Jul 2016

Application of Cu(I)-catalyzed azide–alkyne cycloaddition for the design and synthesis of sequence specific probes targeting double-stranded DNA

  • Svetlana V. Vasilyeva,
  • Vyacheslav V. Filichev and
  • Alexandre S. Boutorine

Beilstein J. Org. Chem. 2016, 12, 1348–1360, doi:10.3762/bjoc.12.128

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  • and Instability of Genomes, Sorbonne Universités, Muséum National d'Histoire Naturelle, INSERM U 1154, CNRS UMR 7196, 57 rue Cuvier, C.P. 26, 75231 Paris cedex 05, France 10.3762/bjoc.12.128 Abstract Efficient protocols based on Cu(I)-catalyzed azidealkyne cycloaddition were developed for the
  • helices by TFO-MGB conjugates was evaluated by gel-shift experiments. The presence of MGB in these conjugates did not affect the binding parameters (affinity and triplex stability) of the parent TFOs. Keywords: binding affinity; click chemistry; Cu(I)-catalyzed azidealkyne cycloaddition; pyrrole
  • experience, these reactions are not suitable for TINA-TFO derivatives due to excessive formation of side products. Copper(I)-catalyzed azidealkyne cycloaddition (CuAAC) as a variation of the Huisgen 1,3-dipolar cycloaddition has become a widely used conjugation method in which the stereoselective formation
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Published 30 Jun 2016

Copper-catalyzed [3 + 2] cycloaddition of (phenylethynyl)di-p-tolylstibane with organic azides

  • Mizuki Yamada,
  • Mio Matsumura,
  • Yuki Uchida,
  • Masatoshi Kawahata,
  • Yuki Murata,
  • Naoki Kakusawa,
  • Kentaro Yamaguchi and
  • Shuji Yasuike

Beilstein J. Org. Chem. 2016, 12, 1309–1313, doi:10.3762/bjoc.12.123

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  • : cycloaddition; copper catalyst; ethynylstibane; organic azide; 1,2,3-triazole; Introduction The 1,3-dipolar azidealkyne cycloaddition (AAC) has been effective for the synthesis of a wide variety of 1,2,3-triazoles [1]. However, this reaction has some limitations such as the requirement of high temperature and
  • 3a with NOBF4 afforded pentavalent organoantimony compound 6 in 85% yield. It is noteworthy that 5-bismuthanotriazole was demetallated upon reaction with NOBF4 to give the corresponding 5-nitroso compound [24]. Conclusion In conclusion, the Cu-catalyzed azidealkyne cycloaddition of (phenylethynyl)di
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Published 23 Jun 2016

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

  • Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

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  • azidealkyne cycloadditions and various A3-coupling reactions are useful procedures in heterocyclic chemistry. However, several methods based on these protocols have also been developed for the synthesis of heterocyclic phosphonates. The 1,2-dihydroisoquinolin-1-ylphosphonates 172 were formed through a
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Published 21 Jun 2016
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