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Search for "bistriazoles" in Full Text gives 8 result(s) in Beilstein Journal of Organic Chemistry.
One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives
- Hans-Ulrich Reissig and
- Fei Yu
Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101
- oxidative dimers in minor amounts has already been observed by Sharpless and co-workers in their original report on CuAAC reactions [4] and was systematically investigated by Burgess et al. [56] who found that the base plays a crucial role during the formation of this type of bistriazoles. This dimerization
Graphical Abstract
Scheme 1: Earlier approaches to multivalent carbohydrate mimetics B, D or F based on enantiopure aminopyran a...
Scheme 2: Synthesis of model compound 3 under conventional conditions and as a one-pot process employing benz...
Scheme 3: One-pot reaction employing enantiopure alkynyl-substituted 1,2-oxazin-4-one derivative 6 leading to...
Scheme 4: One-pot reactions of dihalides 8 and 11 with sodium azide and alkyne 2 leading to symmetric divalen...
Scheme 5: One-pot reactions employing enantiopure alkynyl-substituted 1,2-oxazin-4-one derivative 6 leading t...
Scheme 6: One-pot reaction employing enantiopure alkynyl-substituted 1,2-oxazin-4-ol derivative 19 leading to...
Scheme 7: Reductive ring-openings of 1,2-oxazine derivatives 19 and 23 as simple model compounds by hydrogeno...
Scheme 8: Attempted reductive ring-openings of compound 21 by hydrogenolysis or by samarium diiodide leading ...
A novel bis-triazole scaffold accessed via two tandem [3 + 2] cycloaddition events including an uncatalyzed, room temperature azide–alkyne click reaction
- Ksenia Malkova,
- Andrey Bubyrev,
- Vasilisa Krivovicheva,
- Dmitry Dar’in,
- Alexander Bunev and
- Mikhail Krasavin
Beilstein J. Org. Chem. 2022, 18, 1636–1641, doi:10.3762/bjoc.18.175
- proceeded further, in uncatalyzed fashion at room temperature and yielded, after intramolecular azide–alkyne click reaction novel, structurally intriguing bistriazoles. Keywords: α-acetyl-α-diazomethane sulfonamide; intramolecular click reaction; uncatalyzed; room temperature; 1,2,3-triazoles
- benzaldehydes and propargylamines. Besides the initial formation of the triazole core, the reaction proceeded further, in uncatalyzed fashion at room temperature and yielded structurally intriguing bistriazoles whose structure was unequivocally confirmed by single-crystal X-ray analysis. Compounds are non
Graphical Abstract
Figure 1: (a) Previously developed three-component approach to 1,5-disubstituted 1,2,3-triazoles; (b) double ...
Scheme 1: Results of a trial reaction between 1, o-azidobenzaldehyde (3a) and propargylamine.
Figure 2: Diversely bioactive compounds based on scaffolds A and B.
Scheme 2: Three-component reaction of 1, propargylamine and various o-azidobenzaldehydes.
Figure 3: Aromatic azido aldehydes 3j–l that failed to react with 1 and propargylamine.
Scheme 3: Variations of the amine component in the reactions with 1 and 3a.
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
Graphical Abstract
Figure 1: Marketed drugs with acridine moiety.
Scheme 1: Synthesis of 4-arylacridinediones.
Scheme 2: Proposed mechanism for acridinedione synthesis.
Scheme 3: Synthesis of tetrahydrodibenzoacridinones.
Scheme 4: Synthesis of naphthoacridines.
Scheme 5: Plausible mechanism for naphthoacridines.
Figure 2: Benzoazepines based potent molecules.
Scheme 6: Synthesis of azepinone.
Scheme 7: Proposed mechanism for azepinone formation.
Scheme 8: Synthesis of benzoazulenen-1-one derivatives.
Scheme 9: Proposed mechanism for benzoazulene-1-one synthesis.
Figure 3: Indole-containing pharmacologically active molecules.
Scheme 10: Synthesis of functionalized indoles.
Scheme 11: Plausible mechanism for the synthesis of functionalized indoles.
Scheme 12: Synthesis of spirooxindoles.
Scheme 13: Synthesis of substituted spirooxindoles.
Scheme 14: Plausible mechanism for the synthesis of substituted spirooxindoles.
Scheme 15: Synthesis of pyrrolidinyl spirooxindoles.
Scheme 16: Proposed mechanism for pyrrolidinyl spirooxindoles.
Figure 4: Pyran-containing biologically active molecules.
Scheme 17: Synthesis of functionalized benzopyrans.
Scheme 18: Plausible mechanism for synthesis of benzopyran.
Scheme 19: Synthesis of indoline-spiro-fused pyran derivatives.
Scheme 20: Proposed mechanism for indoline-spiro-fused pyran.
Scheme 21: Synthesis of substituted naphthopyrans.
Figure 5: Marketed drugs with pyrrole ring.
Scheme 22: Synthesis of tetra-substituted pyrroles.
Scheme 23: Mechanism for silica-supported PPA-SiO2-catalyzed pyrrole synthesis.
Scheme 24: Synthesis of pyrrolo[1,10]-phenanthrolines.
Scheme 25: Proposed mechanism for pyrrolo[1,10]-phenanthrolines.
Figure 6: Marketed drugs and molecules containing pyrimidine and pyrimidinones skeletons.
Scheme 26: MWA-MCR pyrimidinone synthesis.
Scheme 27: Two proposed mechanisms for pyrimidinone synthesis.
Scheme 28: MWA multicomponent synthesis of dihydropyrimidinones.
Scheme 29: Proposed mechanism for dihydropyrimidinones.
Figure 7: Biologically active fused pyrimidines.
Scheme 30: MWA- MCR for the synthesis of pyrrolo[2,3-d]pyrimidines.
Scheme 31: Proposed mechanism for pyrrolo[2,3-d]pyrimidines.
Scheme 32: Synthesis of substituted pyrrolo[2,3-d]pyrimidine-2,4-diones.
Scheme 33: Probable pathway for pyrrolo[2,3-d]pyrimidine-2,4-diones.
Scheme 34: Synthesis of pyridopyrimidines.
Scheme 35: Plausible mechanism for the synthesis of pyridopyrimidines.
Scheme 36: Synthesis of dihydropyridopyrimidine and dihydropyrazolopyridine.
Scheme 37: Proposed mechanism for the formation of dihydropyridopyrimidine.
Scheme 38: Synthesis of thiopyrano[4,3-d]pyrimidines.
Scheme 39: Plausible mechanism for the synthesis of thiopyrano[4,3-d]pyrimidines.
Scheme 40: Synthesis of decorated imidazopyrimidines.
Scheme 41: Proposed mechanism for imidazopyrimidine synthesis.
Figure 8: Pharmacologically active molecules containing purine bases.
Scheme 42: Synthesis of aza-adenines.
Scheme 43: Synthesis of 5-aza-7-deazapurines.
Scheme 44: Proposed mechanism for deazapurines synthesis.
Figure 9: Biologically active molecules containing pyridine moiety.
Scheme 45: Synthesis of steroidal pyridines.
Scheme 46: Proposed mechanism for steroidal pyridine.
Scheme 47: Synthesis of N-alkylated 2-pyridones.
Scheme 48: Two possible mechanisms for pyridone synthesis.
Scheme 49: Synthesis of pyridone derivatives.
Scheme 50: Postulated mechanism for synthesis of pyridone.
Figure 10: Biologically active fused pyridines.
Scheme 51: Benzimidazole-imidazo[1,2-a]pyridines synthesis.
Scheme 52: Mechanism for the synthesis of benzimidazole-imidazo[1,2-a]pyridines.
Scheme 53: Synthesis of pyrazolo[3,4-b]pyridine-5-spirocycloalkanedione derivatives.
Scheme 54: Proposed mechanism for spiro-pyridines.
Scheme 55: Functionalized macrocyclane-fused pyrazolo[3,4-b]pyridine derivatives.
Scheme 56: Mechanism postulated for macrocyclane-fused pyrazolo[3,4-b]pyridine.
Scheme 57: Generation of pyrazolo[3,4-b]pyridines.
Scheme 58: Proposed mechanism for the synthesis of pyrazolo[3,4-b]pyridines.
Scheme 59: Proposed mechanism for the synthesis of azepinoindole.
Figure 11: Pharmaceutically important molecules with quinoline moiety.
Scheme 60: Povarov-mediated quinoline synthesis.
Scheme 61: Proposed mechanism for Povarov reaction.
Scheme 62: Synthesis of pyrazoloquinoline.
Scheme 63: Plausible mechanism for pyrazoloquinoline synthesis.
Figure 12: Quinazolinones as pharmacologically significant scaffolds.
Scheme 64: Four-component reaction for dihydroquinazolinone.
Scheme 65: Proposed mechanism for dihydroquinazolinones.
Scheme 66: Synthesis purine quinazolinone and PI3K-δ inhibitor.
Scheme 67: Synthesis of fused benzothiazolo/benzoimidazoloquinazolinones.
Scheme 68: Proposed mechanism for fused benzothiazolo/benzoimidazoloquinazolinones.
Scheme 69: On-water reaction for synthesis of thiazoloquinazolinone.
Scheme 70: Proposed mechanism for the thiazoloquinazolinone synthesis.
Scheme 71: β-Cyclodextrin-mediated synthesis of indoloquinazolinediones.
Scheme 72: Proposed mechanism for synthesis of indoloquinazolinediones.
Figure 13: Triazoles-containing marketted drugs and pharmacologically active molecules.
Scheme 73: Cu(I) DAPTA-catalyzed 1,2,3-triazole formation.
Scheme 74: Mechanism for Cu(I) DAPTA-catalyzed triazole formation.
Scheme 75: Synthesis of β-hydroxy-1,2,3-triazole.
Scheme 76: Proposed mechanism for synthesis of β-hydroxy-1,2,3-triazoles.
Scheme 77: Synthesis of bis-1,2,4-triazoles.
Scheme 78: Proposed mechanism for bis-1,2,4-triazoles synthesis.
Figure 14: Thiazole containing drugs.
Scheme 79: Synthesis of a substituted thiazole ring.
Scheme 80: Synthesis of pyrazolothiazoles.
Figure 15: Chromene containing drugs.
Scheme 81: Magnetic nanocatalyst-mediated aminochromene synthesis.
Scheme 82: Proposed mechanism for the synthesis of chromenes.
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
- a reducing agent in a mixture of water and ethanol as the solvent at 85 °C. In continuation, bistriazoles have been produced using 0.4 mol % of 45 and 10 mg sodium ascorbate as a reducing agent in an ethanol/water mixture at 85 °C. All triazole products were produced in good to high yield (Scheme 7
Graphical Abstract
Scheme 1: Chemical structure of the catalysts 1a and 1b and their catalytic application in CuAAC reactions.
Scheme 2: Synthetic route to the catalyst 11 and its catalytic application in CuAAC reactions.
Scheme 3: Synthetic route of dendrons, illustrated using G2-AMP 23.
Scheme 4: The catalytic application of CuYAu–Gx-AAA–SBA-15 in a CuAAC reaction.
Scheme 5: Synthetic route to the catalyst 36.
Scheme 6: Application of the catalyst 36 in CuAAC reactions.
Scheme 7: The synthetic route to the catalyst 45 and catalytic application of 45 in “click” reactions.
Scheme 8: Synthetic route to the catalyst 48 and catalytic application of 48 in “click” reactions.
Scheme 9: Synthetic route to the catalyst 58 and catalytic application of 58 in “click” reactions.
Scheme 10: Synthetic route to the catalyst 64 and catalytic application of 64 in “click” reactions.
Scheme 11: Chemical structure of the catalyst 68 and catalytic application of 68 in “click” reactions.
Scheme 12: Chemical structure of the catalyst 69 and catalytic application of 69 in “click” reactions.
Scheme 13: Synthetic route to, and chemical structure of the catalyst 74.
Scheme 14: Application of the cayalyst 74 in “click” reactions.
Scheme 15: Synthetic route to, and chemical structure of the catalyst 78 and catalytic application of 78 in “c...
Scheme 16: Synthetic route to the catalyst 85.
Scheme 17: Application of the catalyst 85 in “click” reactions.
Scheme 18: Synthetic route to the catalyst 87 and catalytic application of 87 in “click” reactions.
Scheme 19: Chemical structure of the catalyst 88 and catalytic application of 88 in “click” reactions.
Scheme 20: Synthetic route to the catalyst 90 and catalytic application of 90 in “click” reactions.
Scheme 21: Synthetic route to the catalyst 96 and catalytic application of 96 in “click” reactions.
Scheme 22: Synthetic route to the catalyst 100 and catalytic application of 100 in “click” reactions.
Scheme 23: Synthetic route to the catalyst 102 and catalytic application of 23 in “click” reactions.
Scheme 24: Synthetic route to the catalysts 108–111.
Scheme 25: Catalytic application of 108–111 in “click” reactions.
Scheme 26: Synthetic route to the catalyst 121 and catalytic application of 121 in “click” reactions.
Scheme 27: Synthetic route to 125 and application of 125 in “click” reactions.
Scheme 28: Synthetic route to the catalyst 131 and catalytic application of 131 in “click” reactions.
Scheme 29: Synthetic route to the catalyst 136.
Scheme 30: Application of the catalyst 136 in “click” reactions.
Scheme 31: Synthetic route to the catalyst 141 and catalytic application of 141 in “click” reactions.
Scheme 32: Synthetic route to the catalyst 144 and catalytic application of 144 in “click” reactions.
Scheme 33: Synthetic route to the catalyst 149 and catalytic application of 149 in “click” reactions.
Scheme 34: Synthetic route to the catalyst 153 and catalytic application of 153 in “click” reactions.
Scheme 35: Synthetic route to the catalyst 155 and catalytic application of 155 in “click” reactions.
Scheme 36: Synthetic route to the catalyst 157 and catalytic application of 157 in “click” reactions.
Scheme 37: Synthetic route to the catalyst 162.
Scheme 38: Application of the catalyst 162 in “click” reactions.
Scheme 39: Synthetic route to the catalyst 167 and catalytic application of 167 in “click” reactions.
Scheme 40: Synthetic route to the catalyst 169 and catalytic application of 169 in “click” reactions.
Scheme 41: Synthetic route to the catalyst 172.
Scheme 42: Application of the catalyst 172 in “click” reactions.
Influence of the cis/trans configuration on the supramolecular aggregation of aryltriazoles
- Sara Tejera,
- Giada Caniglia,
- Rosa L. Dorta,
- Andrea Favero,
- Javier González-Platas and
- Jesús T. Vázquez
Beilstein J. Org. Chem. 2019, 15, 2881–2888, doi:10.3762/bjoc.15.282
- -glucopyranosyltriazoles 1a–g and 2a–g [15]. Synthesis of 1,2-cis-/trans-bistriazoles 7a–7g and 8a–8g [15]. Compounds 9 (trans) and 10 (cis) [15]. Synthesis of (1R,2R)- and (1R,2S)-1,2-bis-(4-(4-bromophenyl)-1H-triazol-1-yl)cyclohexane (12 and 14). Gelation test results for compounds 7f, 8a, 8b, 8e, 8f, 9, 10, 12, and 14
Graphical Abstract
Scheme 1: Structures of 4-substituted 1-glucopyranosyltriazoles 1a–g and 2a–g [15].
Scheme 2: Synthesis of 1,2-cis-/trans-bistriazoles 7a–7g and 8a–8g [15].
Scheme 3: Compounds 9 (trans) and 10 (cis) [15].
Scheme 4: Synthesis of (1R,2R)- and (1R,2S)-1,2-bis-(4-(4-bromophenyl)-1H-triazol-1-yl)cyclohexane (12 and 14...
Figure 1: Tube inversion test: gels formed by compounds 7f, 8f, 10, 12, and 14.
Figure 2: SEM images of the xerogels of compounds 7f (DMSO, top left), 8f (DMSO/H2O, 3:1, v/v, top right), 10...
Figure 3: ORTEP representation of the molecular structure of compound 12 (trans configuration) obtained from ...
Figure 4: Crystal packing of compound 12 (trans configuration) in DMSO.
Figure 5: Crystal packing of 10 (cis configuration) in DMSO/H2O (1:1, v/v). Colored lines: π–π stacking inter...
Figure 6: CD spectra of compound 10 (cis) in DMSO/H2O (1:2, v/v) in solution (in black) and as gel (in blue).
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
- . Specifically, the utility of this reaction has been demonstrated by the synthesis of structurally diverse bi- and bis-1,2,3-triazoles. The present review focuses on the synthesis of such bi- and bistriazoles and the importance of using copper-promoted click chemistry (CuAAC) for such transformations. In
- addition, the application of bitriazoles and the related CuAAAC reaction in different fields, including medicinal chemistry, coordination chemistry, biochemistry, and supramolecular chemistry, have been highlighted. Keywords: bistriazoles; click chemistry; cycloaddition; homogeneous catalysis; oxidative
- bistriazoles or their analogues by click chemistry, such as those linked directly or by spacers. The synthetic approaches for the preparation of bi- and bistriazoles are discussed in detail and their application is discussed briefly in each section. Accordingly, the following three types of bi- and
Graphical Abstract
Scheme 1: The synthesis of triazoles through the Huisgen cycloaddition of azides to alkynes.
Scheme 2: The synthesis of symmetrically substituted 4,4'-bitriazoles.
Scheme 3: The synthesis of unsymmetrically substituted 4,4'-bitriazoles.
Scheme 4: The stepwise preparation of unsymmetrical 4,4'-bitriazoles.
Scheme 5: The synthesis of 5,5'-bitriazoles.
Scheme 6: The synthesis of bistriazoles and cyclic 5,5’-bitriazoles under different catalytic systems.
Scheme 7: The double CuAAC reaction between helicenequinone and 1,1’-diazidoferrocene.
Scheme 8: The synthesis of 1,2,3-triazoles and 5,5’-bitriazoles from acetylenic amide.
Scheme 9: The amine-functionalized polysiloxane-mediated divergent synthesis of trizaoles and bitriazoles.
Scheme 10: The cyclic BINOL-based 5,5’-bitriazoles.
Scheme 11: The one-pot click–click reactions for the synthesis of bistriazoles.
Scheme 12: The synthesis of bis(indolyl)methane-derivatized 1,2,3-bistriazoles.
Scheme 13: The sequential, chemoselective preparation of bistriazoles.
Scheme 14: The sequential SPAAC and CuAAC reaction for the preparation of bistriazoles.
Scheme 15: The synthesis of D-mannitol-based bistriazoles.
Scheme 16: The synthesis of ester-linked and amide-linked bistriazoles.
Scheme 17: The synthesis of acenothiadiazole-based bistriazoles.
Scheme 18: The pyrene-appended thiacalix[4]arene-based bistriazole.
Scheme 19: The synthesis of triazole-based tetradentate ligands.
Scheme 20: The synthesis of phenanthroline-2,9-bistriazoles.
Scheme 21: The three-component reaction for the synthesis of bistriazoles.
Scheme 22: The one-pot synthesis of bistriazoles.
Scheme 23: The synthesis of polymer-bearing 1,2,3-bistriazole.
Scheme 24: The synthesis of bistriazoles via a sequential one-pot reaction.
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
- )4][PF6]. However, acetonitrile as co-solvent and the presence of a nitrogen base such as triethylamine, N,N-diisopropylethylamine (DIPEA) or pyridine are required for these catalyses to work. Sharpless also reports the formation of diacetylenes by alkyne homocoupling as well as bistriazoles and 5
Graphical Abstract
Scheme 1: Exemplary 1,3-dipolar cycloaddition of phenylacetylene with phenyl azide [6].
Scheme 2: CuAAC reaction of benzyl azide with (prop-2-yn-1-yloxy)benzene [12].
Scheme 3: Bioconjugation reaction of capsid-bound azide groups with alkynyl-functionalized dye molecules (cow...
Figure 1: Tris(triazolylmethyl)amine ligands for CuAAC applications in bioorganic chemistry: TBTA = tris[(1-b...
Figure 2: Derivatives of 2,2’-bipyridine and 1,10-phenanthroline, commonly used ligands in CuAAC reactions un...
Scheme 4: CuAAC reaction with copper(II) precursor salt and rate-accelerating monodentate phosphoramidite lig...
Scheme 5: Synthesis of 1-(adamant-1-yl)-1H-1,2,3-triazol-4-ylcarbonyl-Phe-Gly-OH by solid-supported Click cat...
Scheme 6: CuAAC reaction with re-usable copper(I)-tren catalyst [129].
Scheme 7: CuAAC test reaction with chlorido[tris(1-benzyl-1H-1,2,3-triazol-4-yl)methanol-κ3N3]copper(I) and a...
Scheme 8: CuAAC model reaction with [Cu2(μ-TBTA-κ4N2,N3,N3’,N3’’)2][BF4]2 [131].
Scheme 9: Application of a (2-aminoarenethiolato)copper(I) complex as homogeneous catalyst for the CuAAC test...
Scheme 10: Application of [CuBr(PPh3)3] as homogeneous catalyst for the CuAAC test reaction of benzyl azide wi...
Figure 3: Phosphinite and phosphonite copper(I) complexes presented by Díez-González [144].
Scheme 11: Effect of additives on the CuAAC test reaction with [(SIMes)CuCl] [149].
Scheme 12: Initiation of the catalytic cycle by formation of the copper acetylide intermediate from [(ICy)2Cu]...
Scheme 13: Early mechanistic proposal by Sharpless [12,42].
Scheme 14: Chemoselective synthesis of a 5-iodo-1,4-disubstituted 1,2,3-triazole [156].
Scheme 15: Mechanistic proposals for the copper-catalyzed azide–iodoalkyne cycloaddition [156].
Scheme 16: 1,3-Dipolar cycloaddition of 3-hexyne catalyzed by [(SIMes)CuBr] [146].
Scheme 17: Mechanistic picture for the cycloaddition of internal alkynes catalyzed by NHC-copper(I) complexes ...
Scheme 18: Catalytic cycle of the CuAAC reaction on the basis of the proposed mechanistic scheme by Fokin and ...
Figure 4: Schematic representation of the single crystal X-ray structures of copper(I) acetylide complexes [Cu...
Figure 5: Acetylide-bridged dicopper complexes with tris(heteroarylmethyl)amine ligand(s) as key intermediate...
Scheme 19: Off-cycle equilibrium between unreactive polymeric copper(I) acetylide species (right) and reactive...
Figure 6: Categories of tris(heteroarylmethyl)amine ligands regarding their binding ability to copper(I) ions ...
Scheme 20: Mechanistic scheme for ligand-accelerated catalysis with tripodal tris(heteroarylmethyl)amine ligan...
Scheme 21: Synthesis of supposed intermediates in the CuAAC’s catalytic cycle [164,187].
Figure 7: Tetranuclear copper acetylide complexes as reported by Weiss (left) [176] and Tasker (middle) [185] and model...
Figure 8: Gibbs free energy diagram for the computed mechanistic pathway of the CuAAC reaction starting from ...
Figure 9: Energy diagram by Ahlquist and Fokin [125].
Scheme 22: Mechanistic proposal for the CuAAC reaction based on DFT calculations by Fokin [125] and our group [186] ([Cu...
Figure 10: ORTEP plot [202,203] of the X-ray powder diffraction crystal structure of (phenylethynyl)copper(I) [(PhC≡CCu)...
Scheme 23: Synthesis of [(PhC≡CCu)2]n as co-product in the Glaser coupling of phenylacetylene in the presence ...
Scheme 24: Mechanistic explanation for the isotopic enrichment in the product triazolide in the presence of th...
Scheme 25: Homogeneous CuAAC catalysis with a bistriazolylidene dicopper complex (0.5 mol %) and comparison wi...
Efficient continuous-flow synthesis of novel 1,2,3-triazole-substituted β-aminocyclohexanecarboxylic acid derivatives with gram-scale production
- Sándor B. Ötvös,
- Ádám Georgiádes,
- István M. Mándity,
- Lóránd Kiss and
- Ferenc Fülöp
Beilstein J. Org. Chem. 2013, 9, 1508–1516, doi:10.3762/bjoc.9.172
- shown that the use of certain acids as additives is also beneficial, as this can further accelerate the formation of the triazole product [64][65][66] and also prevents the accumulation of unwanted byproducts, such as diacetylenes, bistriazoles, etc. [67]. At the same time, byproduct formation is
Graphical Abstract
Figure 1: Examples of 1,2,3-triazoles with various biological activities.
Scheme 1: 1,3-Dipolar azide–alkyne cycloadditions.
Figure 2: Selected bioactive alicyclic β-amino acids.
Figure 3: Experimental setup for the CF reactions.
Scheme 2: Gramm-scale CF synthesis of triazole 22 under conditions B.
