(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

• Luiz Claudio Ferreira Pimentel,
• Lucas Villas Boas Hoelz,
• Henayle Fernandes Canzian,
• Frederico Silva Castelo Branco,
• Andressa Paula de Oliveira,
• Vinicius Rangel Campos,
• Floriano Paes Silva Júnior,
• Rafael Ferreira Dantas,
• Jackson Antônio Lamounier Camargos Resende,
• Anna Claudia Cunha,
• Nubia Boechat and
• Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

• developed by Sharpless and collaborators, to the Huisgen cycloaddition (a 1,3-dipolar cycloaddition reaction to obtain this heterocycle) allowed the regiospecific synthesis of the 1,4-disubstituted isomers with good yields in the presence of copper(I) salts [15][16][17]. Since then, medicinal chemists used

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• -catalyzed Huisgen cycloaddition reaction could provide disubstituted 1,2,3-triazoles. The selective introduction of substituents to three different positions on the 1,2,3-triazole frame can notably improve the features of the molecule. Therefore, practical and cost-effective strategies for the selective

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

• organic frameworks (CNOF, 90) for the preparation of 1,2,3-triazole derivatives substituted at the 1- and 4-positions under green reaction conditions [82]. The CNOF (90) worked well as catalyst for the Huisgen cycloaddition of benzyl azides and aromatic azides (generated from benzyl halides and diazonium

Archangelolide: A sesquiterpene lactone with immunobiological potential from Laserpitium archangelica

• Silvie Rimpelová,
• Michal Jurášek,
• Lucie Peterková,
• Jiří Bejček,
• Vojtěch Spiwok,
• Miloš Majdl,
• Michal Jirásko,
• Miloš Buděšínský,
• Juraj Harmatha,
• Eva Kmoníčková,
• Pavel Drašar and
• Tomáš Ruml

Beilstein J. Org. Chem. 2019, 15, 1933–1944, doi:10.3762/bjoc.15.189

• studied by us and others, there are only scarce reports on the biological activity of archangelolide. Here we present the preparation of its fluorescent derivative based on a dansyl moiety using azide–alkyne Huisgen cycloaddition having obtained the two sesquiterpene lactones from the seeds of Laserpitium

• these compounds for further work including synthetic modifications using azide–alkyne Huisgen cycloaddition. We previously showed the preparation of fluorescent trilobolide conjugates [8] that retained the activity of the parental compounds and proved to be useful for live-cell imaging. In this article

Stereo- and regioselective hydroboration of 1-exo-methylene pyranoses: discovery of aryltriazolylmethyl C-galactopyranosides as selective galectin-1 inhibitors

• Alexander Dahlqvist,
• Axel Furevi,
• Niklas Warlin,
• Hakon Leffler and
• Ulf J. Nilsson

Beilstein J. Org. Chem. 2019, 15, 1046–1060, doi:10.3762/bjoc.15.102

• (aryltriazolyl)methyl galactopyranosyls 10a–n in fair to good yields (42–78% yields) via a copper-catalyzed Huisgen cycloaddition [17][32]. The resulting (aryltriazolyl)methyl galactopyranosyls 10a–n were debenzylated using palladium hydroxide on carbon in a 2:1 cyclohexene and ethanol mixture to give 1a–n in

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

• glycoscience. In this review we present recent advances made in the use of one type of click chemistry, namely the azide–alkyne Huisgen cycloaddition, for the functionalization of gold nanoparticles and their conversion to glyco-gold nanoparticles. Keywords: azide–alkyne Huisgen cycloaddition; carbohydrates

• azide–alkyne Huisgen cycloaddition AuNP surface modification using NCAAC The azide–alkyne 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 azide–alkyne Huisgen cycloaddition (NCAAC) is very slow

• ]. The versatility of the Cu(I)-catalysed azide–alkyne Huisgen cycloaddition (CuAAC) has been demonstrated by its robustness, insensitivity to water and oxygen, and its applicability to a wide range of substrates [42][43][44]. Although the AAC has been used by many groups to modify the surface of AuNPs

Synthesis of ribavirin 2’-Me-C-nucleoside analogues

• Fanny Cosson,
• Aline Faroux,
• Jean-Pierre Baltaze,
• Jonathan Farjon,
• Régis Guillot,
• Jacques Uziel and
• Nadège Lubin-Germain

Beilstein J. Org. Chem. 2017, 13, 755–761, doi:10.3762/bjoc.13.74

• the Huisgen cycloaddition reaction onto the C-alkynyl riboside intermediately obtained [14]. Herein we describe the synthesis of two new carbonated analogues 2 and 3 of RBV modified at the 2’-position (Figure 1). In fact, a quaternization in 2’-position of various nucleosides led to a higher efficacy

• differentiate the 2’ position. After the indium-mediated alkynylation, the obtained alkynyl riboside 8 was submitted to a Huisgen cycloaddition reaction with benzyl azide, under the same conditions as in the previous case, affording the mixture of regioisomeric triazoles 9a and 9b in a 37:63 ratio [14] (Scheme

Sulfamide chemistry applied to the functionalization of self-assembled monolayers on gold surfaces

• Loïc Pantaine,
• Vincent Humblot,
• Vincent Coeffard and
• Anne Vallée

Beilstein J. Org. Chem. 2017, 13, 648–658, doi:10.3762/bjoc.13.64

• have been investigated for the immobilization of a target molecule through a reaction with the terminal groups of the SAMs. The most common methods to covalently functionalize these materials involve the Huisgen cycloaddition between an azide and an alkyne [8][9], Thiol-Michael addition [10][11], amide

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

• of such functionalization using a Sonogashira cross-coupling [26] and an azide–alkyne 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

• group precursor via Huisgen cycloaddition. Supporting Information Supporting Information File 386: Experimental details, NMR spectra, IR spectra, and HRMS for all products and electrochemistry data. Acknowledgments The Swedish Research Council (VR), the Swedish Foundation for Strategic Research (SSF

Creating molecular macrocycles for anion recognition

• Amar H. Flood

Beilstein J. Org. Chem. 2016, 12, 611–627, doi:10.3762/bjoc.12.60

• it was an old reaction, the Huisgen cycloaddition, made good (regioselective) with the aid of copper catalysis. Taking that idea on face value, I reasoned that click chemistry was a new and extremely effective way to make 1,2,3-triazoles. It is not often that either new or newly refined reactions

Synthesis of bi- and bis-1,2,3-triazoles by copper-catalyzed Huisgen cycloaddition: A family of valuable products by click chemistry

• Zhan-Jiang Zheng,
• Ding Wang,
• Zheng Xu and
• Li-Wen Xu

Beilstein J. Org. Chem. 2015, 11, 2557–2576, doi:10.3762/bjoc.11.276

• coupling; Introduction Since its discovery by Huigsen and co-workers fifty years ago [1][2][3][4], the Huisgen cycloaddition of azides to alkynes has gained much attention due to its potential to yield a wide variety of triazoles with structurally diverse and functionalized groups, especially with respect

• , powder or nanoparticles) in the presence or absence of Cu(II) in aqueous media also provides the key active Cu(I) in some CuAAC reactions. As an important supplement to the classic Huisgen cycloaddition promoted by copper catalysis, this review will deal with the copper-catalyzed syntheses of bi- and

• the CuAAC reaction, the 5,5'-bitriazoles were usually considered as an undesired side product or impurity in the Huisgen cycloaddition. In general, they are the oxidative coupling product of the triazole-copper species. The 5,5'-bitriazoles were usually formed as the major product by the facilitation

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

• Nicolas Desbois Sandrine Pacquelet Adrien Dubois Clement Michelin Claude P. Gros Université de Bourgogne Franche-Comté, ICMUB (UMR CNRS 6302), 9 Avenue Alain Savary, BP 47870, 21078 Dijon Cedex, France 10.3762/bjoc.11.239 Abstract The Cu(I)-catalysed Huisgen cycloaddition, known as “click

• radiometal for application in PET. The ‘Huisgen’ Cu(I)-catalyzed cycloaddition appears to be a good answer to access to such bimodal agents [7]. For example, Caravan and co-workers have described an MRI-PET agent using a copper(I)-catalyzed Huisgen cycloaddition [8]. To prepare new multimodal agents, we have

• ., cyclooctyne DOTA derivatives. Selected ligands for the copper(I)-catalyzed Huisgen cycloaddition. Structure of different bimetallic complexes 5–7. Synthesis of 8a,b and 9a–d. (i) for 8a: THF, N2, Cu(OAc)2·H2O, rt 15 min; for 8b: GaCl3 0.114 M in dry pyridine, reflux 1.5 h. (ii) for 9a: CHCl3/MeOH, Cu(OAc)2

Expeditive synthesis of trithiotriazine-cored glycoclusters and inhibition of Pseudomonas aeruginosa biofilm formation

• Meriem Smadhi,
• Sophie de Bentzmann,
• Anne Imberty,
• Marc Gingras,
• Raoudha Abderrahim and
• Peter G. Goekjian

Beilstein J. Org. Chem. 2014, 10, 1981–1990, doi:10.3762/bjoc.10.206

• -triazine (2) as a key precursor [37]. The glycosyl units were incorporated via Cu(I)-catalyzed Huisgen cycloaddition with protected or unprotected glycosyl azides. We first investigated the Cu-catalyzed azide–alkyne cycloaddition (CuAAC) of acetyl protected β-D-galactopyranosyl azide 3 [38], to tris

Clicked and long spaced galactosyl- and lactosylcalix[4]arenes: new multivalent galectin-3 ligands

• Silvia Bernardi,
• Paola Fezzardi,
• Gabriele Rispoli,
• Stefania E. Sestito,
• Francesco Peri,
• Francesco Sansone and
• Alessandro Casnati

Beilstein J. Org. Chem. 2014, 10, 1672–1680, doi:10.3762/bjoc.10.175

• have been widely studied in their scope and limitations [10][31]. In particular, the Huisgen cycloaddition reaction was first applied to a calixarene in 2000 by Santoyo-González [32]. Later on, Marra et al. [33] demonstrated that the copper-catalyzed azide–alkyne cycloaddition (CuAAC) [34][35] at room

Design and synthesis of multivalent neoglycoconjugates by click conjugations

• Feiqing Ding,
• Li Ji,
• Ronny William,
• Hua Chai and
• Xue-Wei Liu

Beilstein J. Org. Chem. 2014, 10, 1325–1332, doi:10.3762/bjoc.10.134

• conditions in hand, we focused on performing a Huisgen cycloaddition reaction. The scope and generality of this method to prepare 3-tosylamino-2,3-dideoxyneoglycoconjugates 4 with the assistance of copper sulfate and sodium ascorbate was examined extensively. A range of α-alkyne-3-tosylamino-2,3

• conjugations to microwave irradiation. All the reactions were completed in considerably shorter reaction times of less than 30 min for the Huisgen cycloaddition of alkenes and azides catalyzed by copper sulfate and sodium ascorbate, affording the corresponding products in good to excellent yields in each case

• (Table 3, method B). This result showed that the synthesis of 3-tosylamino-2,3-dideoxyneoglycoconjugates via copper-catalyzed Huisgen cycloaddition is highly efficient under microwave irradiation. In carbohydrate recognition events, higher multivalent interactions are absolutely essential as the

Atherton–Todd reaction: mechanism, scope and applications

• Stéphanie S. Le Corre,
• Mathieu Berchel,
• Hélène Couthon-Gourvès,
• Jean-Pierre Haelters and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2014, 10, 1166–1196, doi:10.3762/bjoc.10.117

Advancements in the mechanistic understanding of the copper-catalyzed azide–alkyne cycloaddition

• Regina Berg and
• Bernd F. Straub

Beilstein J. Org. Chem. 2013, 9, 2715–2750, doi:10.3762/bjoc.9.308

• . The classical thermal Huisgen cycloaddition of organoazides and alkynes proceeds very slowly even at high temperatures, and gives a mixture of 1,4- and 1,5-disubstituted 1,2,3-triazoles (Scheme 1). In 2002, the groups of Meldal and Sharpless independently discovered a copper-catalyzed variant of

The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates

• Katharina Gallas,
• Gerit Pototschnig,
• Florian Adanitsch,
• Arnold E. Stütz and
• Tanja M. Wrodnigg

Beilstein J. Org. Chem. 2012, 8, 1619–1629, doi:10.3762/bjoc.8.185

• chemistry (Huisgen cycloaddition) [4][5], glycosylation protocols [6][7], and Staudinger ligation [8], just to mention the most prominent examples. However, many applications in this respect require a ligation method that is functional in aqueous medium, and, for economic purposes in general, protecting

Parallel solid-phase synthesis of diaryltriazoles

• Matthias Wrobel,
• Jeffrey Aubé and
• Burkhard König

Beilstein J. Org. Chem. 2012, 8, 1027–1036, doi:10.3762/bjoc.8.115

• protein–protein interactions. Keywords: chemical diversity; Huisgen cycloaddition; library synthesis; peptidomimetics; solid phase synthesis; triazole; Introduction The α-helix was the first-described secondary structure of peptides discovered by Linus Pauling in 1951 [1]. With about 30% of the amino

Thiophene-based donor–acceptor co-oligomers by copper-catalyzed 1,3-dipolar cycloaddition

• Stefanie Potratz,
• Amaresh Mishra and
• Peter Bäuerle

Beilstein J. Org. Chem. 2012, 8, 683–692, doi:10.3762/bjoc.8.76

• . Conclusion In summary, a series of novel thiophene-1,2,3-triazole co-oligomers was synthesized in good to excellent yields by a three-component two-step procedure using copper-catalyzed [3 + 2]-Huisgen cycloaddition reactions. Spectroscopic and redox properties of selected donor–acceptor–donor derivatives

Azobenzene dye-coupled quadruply hydrogen-bonding modules as colorimetric indicators for supramolecular interactions

• Yagang Zhang and
• Steven C. Zimmerman

Beilstein J. Org. Chem. 2012, 8, 486–495, doi:10.3762/bjoc.8.55

• % yield. Alternatively, azobenzene dye 16 underwent a room-temperature copper-catalyzed azide–alkyne Huisgen cycloaddition with DeUG alkyne 17 to give triazole 18 in 71% yield. Azobenzene coupled DAN modules 5, 8, and 10 are bright orange–red in color, and azobenzene coupled DeUG modules 12 and 18 are

• Huisgen cycloaddition (click reaction). The click approach began with the readily available and inexpensive starting material, 4-aminobenzoic acid (Scheme 4), which was diazotized and treated with phenol to afford 13 in 65% yield, comparable to published procedures [52][53][54]. To install the azide

Synthesis of 2-amino-3-arylpropan-1-ols and 1-(2,3-diaminopropyl)-1,2,3-triazoles and evaluation of their antimalarial activity

• Matthias D’hooghe,
• Stéphanie Vandekerckhove,
• Karen Mollet,
• Karel Vervisch,
• Stijn Dekeukeleire,
• Liesbeth Lehoucq,
• Carmen Lategan,
• Peter J. Smith,
• Kelly Chibale and
• Norbert De Kimpe

Beilstein J. Org. Chem. 2011, 7, 1745–1752, doi:10.3762/bjoc.7.205

• 1,2,3-triazole moiety instead. A powerful methodology towards the synthesis of functionalized 1,2,3-triazoles involves the Cu(I)-catalyzed azide-alkyne Huisgen cycloaddition (CuAAC) [33], which has gained major interest from the synthetic community due to its high efficiency and selectivity. Eligible

Advances in synthetic approach to and antifungal activity of triazoles

• Kumari Shalini,
• Nitin Kumar,
• Sushma Drabu and
• Pramod Kumar Sharma

Beilstein J. Org. Chem. 2011, 7, 668–677, doi:10.3762/bjoc.7.79

• nitrogen atoms. However, flash vacuum pyrolysis at 500 °C leads to loss of molecular nitrogen (N2) to produce aziridine. Certain triazoles are relatively easy to cleave by ring–chain tautomerism. Synthesis of triazoles Substituted 1,2,3-triazoles can be produced by the azide–alkyne Huisgen cycloaddition in

A biphasic oxidation of alcohols to aldehydes and ketones using a simplified packed- bed microreactor

• Andrew Bogdan and
• D. Tyler McQuade

Beilstein J. Org. Chem. 2009, 5, No. 17, doi:10.3762/bjoc.5.17

• catalysts functionalized with an acetylene moiety can be tethered to AO using a Huisgen cycloaddition [39]. Azide-functionalized AO resin (AO-N3, 2) was prepared by treating AO with sodium azide (Scheme 1) [41]. The coupling of 4-hydroxy-TEMPO 3 with propargyl bromide (4) using sodium hydride yielded the