- Functionalization of 1,2,3-Triazole to Pyrimidine, Pyridine, Pyrazole, and Isoxazole Fluorophores with Antimicrobial Activity
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Abstract: The multi-component reaction of diacetyl triazole derivative with ethyl cyanoacetate and various aromatic aldehydes according to the conventional and solvent free methods leads to the corresponding 2-oxonicotinonitriles. A number of chalcones ha
- El-Sayed, H. A.,Hamid, A. M. Abdel,Mohammed, S. M.,Morsy, H. A.,Moustafa, A. H.
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- Synthesis and bioactivity evaluation of eugenol hybrids obtained by Mannich and 1,3 dipolar cycloaddition reactions
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Design, synthesis, and bioactivity evaluation of novel mannich bases (2a-2j) and triazole-chalcone derivatives (7a-7k) of Eugenol 1 were reported. Among all the derivatives tested for antiproliferative activity, di-amine manich derivative 2b (32.92 μM), a
- Buduma, Komuraiah,Kumar A, Niranjana,Srinivas KVN, Satya,Kumar J, Kotesh,Chinde, Srinivas,Domatti, Anand Kumar,Kumar, Yogesh,Grover, Paramjit,Tiwari, Ashok,Khan, Feroz
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- Targeting the MKK7-JNK (Mitogen-Activated Protein Kinase Kinase 7-c-Jun N-Terminal Kinase) Pathway with Covalent Inhibitors
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The protein kinase MKK7 is linked to neuronal development and the onset of cancer. The field, however, lacks high-quality functional probes that would allow for the dissection of its detailed functions. Against this background, we describe an effective co
- Wolle, Patrik,Hardick, Julia,Cronin, Shane J. F.,Engel, Julian,Baumann, Matthias,Lategahn, Jonas,Penninger, Josef M.,Rauh, Daniel
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- Combinatorial synthesis of new fluorescent scaffolds using click chemistry
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Azides and acetylenes are bio-orthogonal functional groups that can be readily coupled using copper(I)- or ruthenium(II)- catalyzed 1,3-dipolar cycloaddition reactions. Using non-fluorescent aromatic azides and aromatic acetylenes, covering a range of electron rich and poor building blocks, the Huisgen cycloaddition afford 1,4-disubstituted or 1,5-disubstituted 1,2,3-triazoles. Using a combinatorial approach by running reaction in parallel in polypropylene 96-well plates we discovered several new fluorescent 1,2,3-triazoles scaffolds. These compounds show diverse interactions with biomolecules that could find applications in biology in, for example, fluorescence microscopy or biomolecule quantification.
- Cleemann, Felix,Karuso, Peter,Kum-Cheung, Wendy Loa
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supporting information
(2021/12/08)
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- Immobilization of vitamin B1 on the magnetic dialdehyde starch as an efficient carbene-type support for the copper complexation and its catalytic activity examination
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Since the starch biopolymer is an available and inexpensive matrix with modifiable functionality and stabilization capability for metal ions, in this report, we oxidized it to dialdehyde form for the further functionalization with vitamin B1 as a green σ-donor and π-acceptor carbene type ligand. Immobilization of vitamin B1 on this biopolymer was done through imine bond formation between NH2 groups of aminopyrimidine segment of vitamin B1 and aldehyde functional groups of starch oxide. Thiazolium heterocycle part in this biomolecule provided a carbene type precursor for the metal complexation. After the magnetization process by using of Fe3O4 nanoparticles that lead to quick and facile magnetic separation and metal catalyst recycling, copper ions immobilized on the magnetic support (5.9 wt% Cu, 0.93 mmol/g). The prepared copper N-heterocyclic carbene complex (Fe3O4@DAS@VB1@CuCl nanocomposite) was characterized by FT-IR, SEM, EDX, XRD, VSM, TGA and ICP-OES analysis and then its catalytic activity investigated in azidonation of arylboronic acids and also one-pot coupling reaction of the synthesized aryl azides with phenylacetylene. 1,4-Diaryl 1,2,3-triazoles were obtained in excellent yields (≥90%) at proper reaction times (30–200 min). The magnetic catalyst was recovered by a magnetic field and reused in azidation reaction up to 7 cycle.
- Abbaspour, M.,Mohammadi Ziarani, G.,Rafiee, F.
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- Small Molecule Control of Morpholino Antisense Oligonucleotide Function through Staudinger Reduction
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Conditionally activated, caged morpholino antisense agents (cMOs) are tools that enable the temporal and spatial investigation of gene expression, regulation, and function during embryonic development. Cyclic MOs are conformationally gated oligonucleotide analogs that do not block gene expression until they are linearized through the application of an external trigger, such as light or enzyme activity. Here, we describe the first examples of small molecule-responsive cMOs, which undergo rapid and efficient decaging via a Staudinger reduction. This is enabled by a highly flexible linker design that offers opportunities for the installation of chemically activated, self-immolative motifs. We synthesized cyclic cMOs against two distinct, developmentally relevant genes and demonstrated phosphine-triggered knockdown of gene expression in zebrafish embryos. This represents the first report of a small molecule-triggered antisense agent for gene knockdown, adding another bioorthogonal entry to the growing arsenal of gene knockdown tools.
- Chen, James K.,Darrah, Kristie,Deiters, Alexander,Lukasak, Bradley,Tsang, Michael,Wesalo, Joshua
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supporting information
p. 18665 - 18671
(2021/11/16)
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- Design, click conventional and microwave syntheses, DNA binding, docking and anticancer studies of benzotriazole-1,2,3-triazole molecular hybrids with different pharmacophores
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Despite the availability of some drugs, there is an urgent need for effective anti-cancer medication. It is due to various side effects and non-functionality of the present drugs; especially at the late stage of cancer. Therefore, three series (4a-e, 6a-e and 8a-j; 21 compounds) of benzotriazole-1,2,3-triazole hybrids (carrying different pharmacophores) have been designed and synthesized (by both conventional and microwave syntheses) through the Cu(I)-catalyzed click 1,3-dipolar cycloaddition reaction of the propargylated benzotriazole with the appropriate aliphatic, aromatic and phenyl/benzyl acetamide azides. The syntheses times were from 6 to 12 h and 4 to 8 min in conventional and microwave syntheses. The yields were 80 to 86percent and 89 to 95percent in conventional and microwave syntheses; confirming microwave synthesis as an economic and eco-friendly method. These compounds were characterized by proper spectroscopic methods. The anticancer activities with A549 and H1299 lung cancer cell lines were in the range of 70.0 to 90.0percent for 4a-e series, 78.0 to 90.0percent for 6a-e series and 81.0 to 90.0percent for 8a-j series. The reported compounds showed good DNA binding constants in the range of 1.3 × 103 to 11.90 × 105 M?1. The docking results suggested strong DNA bindings of the reported compounds in the minor grooves of DNA; through hydrogen bonding and hydrophobic interactions. The quite good anticancer activities and high DNA binding constants have indicated that the reported molecules may be future anticancer agents.
- Alharbi, Khalid,Ali, Imran,Aljuhani, Ateyatallah,Alraqa, Shaya Yahya,Aouad, Mohamed Reda,Rezki, Nadjet
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- New α-Hydroxy-1,2,3-triazoles and 9H-Fluorenes-1,2,3-triazoles: H Synthesis and Evaluation as Glycine Transporter 1 Inhibitors
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Two series of new compounds containing 1,2,3-triazole moiety were designed as putative GlyT1 inhibitors aiming the discovery of new hits with activity in cognitive disorders. 1,4-Disubstituted α-hydroxy-1,2,3-triazoles were obtained as racemates in moderate to good yields by the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction (click chemistry) as the key step between propargyl alcohols and aryl azides, previously prepared from anilines or boronic acids. Benzo[c]chromene-triazoles were planned to be obtained by palladium-catalyzed C?H activation using [bis(trifluoroacetoxy)iodobenzene] (PhI(TFA)2) of some α-hydroxy-1,2,3-triazoles, since benzo[c]chromenes are also privileged groups with several biological activities, including to the central nervous system. Unexpectedly, 9H-fluorenes-1,2,3-triazoles, instead of benzo[c]chromenetriazoles, were obtained by Friedel-Crafts alkylation reaction. The two series of compounds were tested for inhibition of the glycine transporter (rat GlyT1 isoform) but only the α-hydroxy-1,2,3-triazole 9b was active (half maximal inhibitory concentration (IC50) = 8.0 μM).
- Buarque, Camilla D.,Guimar?es, Marilia Z.,López?Corcuera, Beatriz,Neto, Jo?o Gon?alves,No?l, Fran?ois,Silva, Rafaela R.,da Silva, Veronica D.
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p. 1258 - 1269
(2020/10/14)
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- Methyl-2,2-difluoro-2-(fluorosulfonyl) acetate (MDFA)/copper (I) iodide mediated and tetrabutylammonium iodide promoted trifluoromethylation of 1-aryl-4-iodo-1,2,3-triazoles
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While several methods are available for the synthesis of a host of trifluoromethylated heterocycles, very few of them have been applied to access 4-trifluoromethylated 1,2,3-triazoles. We report herein a general methodology for the trifluoromethylation of 1-aryl-4-iodo-1, 2, 3-triazoles. Tetrabutylammonium iodide (TBAI) has been shown to provide enhanced conversion in these CuI-mediated reaction using methyl 2,2-difluoro-2-(fluorosulfonyl)acetate (MDFA). The method exhibited broad functional group tolerance and was applied to the synthesis of a library of 1-aryl-4-trifluoromethyl-1,2,3-triazoles on the multi-gram scale.
- Arunachalam, Pirama Nayagam,Chandran, Thirumurugan Kothandarama,Corte, James R.,Gupta, Anuradha,Kumar, Hemantha,Mathur, Arvind,Nimje, Roshan Y.,Panja, Chiradeep,Puttaramu, Jayashankara Vaderapura
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supporting information
(2020/06/08)
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- Synthetic approaches, anticancer potential, HSP90 inhibition, multitarget evaluation, molecular modeling and apoptosis mechanistic study of thioquinazolinone skeleton: Promising antibreast cancer agent
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New series of compounds bearing 2-thioquinazolinone scaffold were designed, synthesized as HSP90 inhibitors. Anti-proliferative activity of the synthesized compounds was evaluated against HCT-116, Hela and MCF-7 cell lines and compound 5k was found to be
- El-Messery, Shahenda M.,El-Shafey, Hamed W.,Goda, Fatma E.,Gomaa, Rania M.
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- Synthesis, characterization, PASS prediction and in silico ADME studies of ester and ether linked 1,4-disubstituted 1,2,3-triazoles derivatives via click approach
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In the present investigation, we focused our interest on the synthesis of pharmacophoric units (quinoline and 1,2,3-triazole) linked through ester (3a-b) and (substituted aromatic ring and 1,2,3-triazole) linked through an ether (3c-h). The synthesis invo
- Krishnaswamy,Raghuram Shetty,Roopa,Banu, Salma,Preritha,Rajeshwari,Ravikumar,Pruthviraj,Aruna Kumar,Sreenivasa
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p. 1857 - 1864
(2020/09/02)
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- Heterogeneous photocatalysis of azides: Extending nitrene photochemistry to longer wavelengths
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The photodecomposition of azides to generate nitrenes usually requires wavelengths in the 300 nm region. In this study, we show that this reaction can be readily performed in the UVA region (368 nm) when catalyzed by Pd-decorated TiO2. In aqueous medium the reaction leads to amines, with water acting as the H source; however, in non-protic and non-nucleophilic media, such as acetonitrile, nitrenes recombine to yield azo compounds, while azirine-mediated trapping occurs in the presence of nucleophiles. The heterogeneous process facilitates catalyst separation while showing great chemoselectivity and high yields.
- Argüello, Juan E.,Lanterna, Anabel E.,Lemir, Ignacio D.,Scaiano, Juan C.
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supporting information
p. 10239 - 10242
(2020/10/02)
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- SNAr azidation of phenolic functions utilizing diphenyl phosphorazidate
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A useful method for the synthesis of aryl azides via SNAr reaction of phenol derivatives using diphenyl phosphorazidate (DPPA) as an azidation reagent was developed. Various phenol derivatives bearing electron-withdrawing groups were converted into the corresponding aryl azides in a single step. This method is easy to perform and enables the preparation of aryl azides without the use of explosive azide sources.
- Ishihara, Kotaro,Shioiri, Takayuki,Matsugi, Masato
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supporting information
(2019/12/27)
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- Preparation of aryl azides of aryl boronic acids and one-pot synthesis of 1,4-diaryl-1,2,3-triazoles by a magnetic cysteine functionalized GO–CuI/II nanocomposite
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A mixed CuI/CuIIcatalyst based on magnetic cysteine functionalized graphene oxide (CuI/II@Cys-MGO) was prepared and used for the azidonation reaction of aryl boronic acids and one-pot synthesis of 1,4-diaryl ?1,2,3-triazoles. Aryl azides were obtained in good yields and short reaction times via cross-coupling of aryl boronic acids with sodium azide in the presence of CuII catalytic species in this catalytic system. The azide-alkyne cycloaddition reaction was catalyzed by CuI catalytic species in CuI/II@Cys-MGO nanocomposite.
- Rafiee, Fatemeh,Khavari, Parvaneh
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- Synthesis of novel 1,2,3-triazole based artemisinin derivatives and their antiproliferative activity
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Two series of novel 1,2,3-triazole based artemisinin derivatives were designed, synthesized via a copper(i)-catalyzed azide alkyne cycloaddition (CuAAC) reaction and investigated for their antiproliferative activity by MTT assay against various human canc
- Kapkoti, Deepak Singh,Singh, Shilpi,Luqman, Suaib,Bhakuni, Rajendra Singh
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p. 5978 - 5995
(2018/04/23)
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- A reliable one-pot synthesis of aryl azides from aryl amines using organotin azides as effective and recoverable reagents
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A mild and mass-efficient procedure based on the one-pot diazotization-azidodediazoniation of aromatic amines is described. A wide range of aryl azides are obtained in moderate to high yields by using tributyltin azide as an effective and reusable azide source in the presence of p-toluenesulfonic acid at room temperature. The method was also successfully applied employing an insoluble polymer-supported organotin azide.
- Godoy Prieto, Leonela,Lo Fiego, Marcos J.,Chopa, Alicia B.,Lockhart, María T.
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supporting information
p. 26 - 32
(2016/12/18)
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- Glucose promoted facile reduction of azides to amines under aqueous alkaline conditions
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A quick and efficient method for the reduction of azides to amines in water using d-glucose and KOH as green reagents is reported. The protocol is simple, inexpensive, scalable, and can be applied to different aromatic, heteroaromatic and sulphonyl azides. A high level of chemoselectivity is observed for azide reduction in the presence of other reducible functionalities like cyano, nitro, ether, ketone, amide and acid. The reaction gets completed in a short time (5-20 minutes), and furnishes the amines in high yield (85-99%). Unlike conventional hydrogenations, this reduction protocol does not require any metal catalyst, elaborate experimental setup or use of high-pressure equipment.
- Chandna, Nisha,Kaur, Fatehjeet,Kumar, Shobhna,Jain, Nidhi
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supporting information
p. 4268 - 4271
(2017/09/29)
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- Copper-Mediated Functionalization of Aryl Trifluoroborates
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This paper describes the Cu(OTf)2-mediated coupling of aryl and heteroaryl trifluoroborates with tetrabutylammonium or alkali metal salts to form C-O, C-N, and C-halogen bonds. The reactions proceed under mild conditions (often room temperature over 16 hours) with carboxylate, halide, and azide salts, all nucleophiles that have been underrepresented in the copper cross-coupling literature. Preliminary results show that copper salts bearing weakly coordinating X-type ligands are essential for enabling these transformations to proceed under mild conditions.
- Schimler, Sydonie D.,Sanford, Melanie S.
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supporting information
p. 2279 - 2284
(2016/10/06)
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- Synthesis, characterization, and antimicrobial activity of novel (E)-1-(aryl)-3-{3, 5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones
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The new chalcone derivatives containing the 1,2,3-triazole ring system, namely, (E)-1-(aryl)-3-{3,5-dimethoxy-4-[(1-(aryl)-1H-1,2,3-triazol-4-yl)methoxy]phenyl}prop-2-en-1-ones, were synthesized in 65–88% yield by the “click chemistry” reactions of substituted acetophenones, 4-hydroxy-3,5-dimethoxy-benzaldehyde, and different substituted azides. The structure of the compounds was determined by the FT-IR, 1H NMR, 13C NMR, and mass spectroscopic analyses. Compounds 6a–6l were screened for in vitro antimicrobial activity by the agar disc diffusion method.
- Subhashini,Sravanthi, Ch.,Sravanthi,Shivaraj
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p. 1405 - 1411
(2016/08/12)
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- An aryl azide, and aryl 1, 2, 3 triazole spiro the synthetic method of the compound of
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The invention discloses a synthetic method of aryl azide and an aryl 1, 2, 3-triazole spiro-compound. The method comprises the following steps: adding substituted arylamine into a reaction container, dissolving the arylamine by methanol, adjusting the pH value to 5-8, introducing methyl nitrite, and reacting for 1-3 hours to obtain a reaction liquid; adding sodium azide into the reaction liquid, monitoring the reaction progress by TLC and reacting for 1-5 hours and posttreating to obtain a pure product of the aryl azide I; adding the product of the aryl azide I, oxonium ylide and an organic solvent into the reaction container, monitoring the reaction progress by TLC, reacting for 36-72 hours at 50-70 DEG C and posttreating to obtain the aryl 1, 2, 3-triazole spiro-compound. The aryl azide is synthesized by methyl nitrite which replaces sodium nitrite and carries out a diazo-reaction with hydrochloric acid, so that the method avoids generation of nitric oxide and nitric dioxide in the reaction process, thereby satisfying the concept of green chemistry.
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Paragraph 0072
(2016/10/10)
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- Design, synthesis and biological evaluation of ciprofloxacin tethered bis-1,2,3-triazole conjugates as potent antibacterial agents
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A series of new bis-1,2,3-triazole linked ciprofloxacin conjugates was designed, synthesized and evaluated in?vitro antibacterial activity against a panel of clinically relevant bacteria. A significant part of the compounds displayed enhanced activity against both Gram-positive and Gram-negative species of bacteria as compared to the parent drug. Additionally, negligible toxicity profile of compounds indicates that they may act a good antibiotic in future. Despite relatively small number of synthesized conjugates, it was possible to observe important dependences between their structure and activity.
- Kant, Rama,Singh, Vishal,Nath, Gopal,Awasthi, Satish Kumar,Agarwal, Alka
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p. 218 - 228
(2016/09/09)
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- DABCO/AcOH Jointly Accelerated Copper(I)-Catalysed Cycloaddition of Azides and Alkynes on Water at Room Temperature
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An expeditious room temperature protocol for the synthesis of 1,4-disubstituted 1,2,3-triazoles from terminal alkynes and substituted azides has been achieved using the combination of CuSO4-ascorbate/1,4-diazabicyclo[2.2.2]octane/acetic acid. This expeditious protocol is applicable to aryl, alkyl, and sulfonyl azides. Acetic acid accelerates the protonation of cuprated triazole and thus avoids the possible side reactions. Devoid of acetic acid, the reaction pathway alters to the ketinimine route and results in the formation of sulfonamides.
- Sarode, Prashant B.,Bahekar, Sandeep P.,Chandak, Hemant S.
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supporting information
p. 2681 - 2684
(2016/11/26)
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- A library of 1,2,3-triazole-substituted oleanolic acid derivatives as anticancer agents: Design, synthesis, and biological evaluation
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A series of novel oleanolic acid coupled 1,2,3-triazole derivatives have been designed and synthesized by employing a Cu(i) catalyzed Huisgen 1,3-dipolar cycloaddition reaction. The anti-proliferative evaluation indicated that some compounds exhibited exc
- Wei, Gaofei,Luan, Weijing,Wang, Shuai,Cui, Shanshan,Li, Fengran,Liu, Yongxiang,Liu, Yang,Cheng, Maosheng
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p. 1507 - 1514
(2015/01/30)
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- A reagent for safe and efficient diazo-transfer to primary amines: 2-azido-1,3-dimethylimidazolinium hexafluorophosphate
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Organic azides were prepared from primary amines in high yields by a metal free diazo-transfer reaction using 2-azido-1,3-dimethylimidazolinium hexafluorophosphate (ADMP), which is safe and stable crystalline. The choice of base was important in the diazo-transfer reaction. In general, 4-(N,N-dimethyl)aminopyridine (DMAP) was efficient, but a stronger base such as alkylamine or DBU was more appropriate for the reaction of nucleophilic primary amines. X-ray single crystal structural analysis and geometry optimization using density functional theory (B3LYP/6-31G**) were conducted to study the ADMP structure, and the diazo-transfer reaction mechanism was explained with the help of the results of these analyses. the Partner Organisations 2014.
- Kitamura, Mitsuru,Kato, So,Yano, Masakazu,Tashiro, Norifumi,Shiratake, Yuichiro,Sando, Mitsuyoshi,Okauchi, Tatsuo
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p. 4397 - 4406
(2014/06/23)
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- PdCl2 catalyzed efficient assembly of organic azides, CO, and alcohols under mild conditions: A direct approach to synthesize carbamates
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A simple and readily available PdCl2 catalyzed carbamate synthesis method via isocyanate generation and application in situ has been developed. This chemistry provides an efficient and practical approach to synthesize carbamates from simple organic azides, CO atmosphere and alcohols. The broad scope, mild and neutral conditions, and only N2 as the byproduct make this transformation very useful. Moreover, simple examples of modification of bioactive molecules and construction of macrocycles were achieved through this protocol. This journal is the Partner Organisations 2014.
- Ren, Long,Jiao, Ning
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supporting information
p. 3706 - 3709
(2014/04/03)
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- Click chemistry on diterpenes: Anti-inflammatory activity of the acetylenic derivatives of levopimaric acid and products of their transformations
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Anti-inflammatory activity of amides of levopimaric acid (LpA) with acetylenic moiety and its esters with 4-R-triazolic substitutions was investigated using histamine-induced mice paw edema model. The synthesized LpA derivatives possess anti-inflammatory
- Vasilevsky, Sergey F.,Baranov, Denis S.,Govdi, Anastasia I.,Sorokina, Irina V.,Tolstikova, Tatyana G.,Tolstikov, Genrikh A.,Alabugin, Igor V.
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p. 145 - 157
(2014/08/18)
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- Synthesis, anti-inflammatory and antioxidant activity of ring-a-monosubstituted chalcone derivatives
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A library of ring-A-monosubstituted chalcone derivatives (4a-4i, 5a and 5b) was designed and synthesised. The structures as well as the identities of these compounds were established on the basis of spectral (1H NMR, 13C NMR, FT-IR and Mass) and elemental (C, H, N) analyses. All the derivatives were evaluated for their anti-inflammatory and antioxidant activities in vitro using the inhibition of protein denaturation and 2,2-diphenyl-1-picrylhydrazyl radical scavenging assays, respectively. The results indicated a promising anti-inflammatory activity for most of the synthesised compounds with many derivatives showing activities similar to or greater than that of the standard. The sulphonamide-substituted chalcones 4h, 4i, 5a and 5b were found to be the most active derivatives across the concentration range tested. However, all the derivatives exhibited rather mild antioxidant activity compared to the ascorbic acid standard. Interestingly, it was observed that the unsubstituted parent chalcone was one of the optimal compounds with only the trifluoromethyl analogue 4a showing better activity as an antioxidant. The two regioisomeric aminochalcones and 4′-cyanochalcone 4b also seemed to possess decent antioxidant potential.
- Iqbal, Hiba,Prabhakar, Visakh,Sangith, Atul,Chandrika, Baby,Balasubramanian, Ranganathan
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p. 4383 - 4394
(2015/04/22)
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- Selective azidation of aryl halides to aryl azides promoted by proline and CuFeO2
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An efficient and selective azidation of aryl halides by reacting sodium azide with aryl halides is described. The heterogeneous nature of the copper(Ι) catalyst, which catalyzes the cross-coupling reactions, and the antiviral and antibacterial properties
- Hajipour, Abdol Reza,Karimzadeh, Morteza,Ghorbani, Sirous
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supporting information
p. 2903 - 2907
(2015/01/16)
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- Chemoselective reduction of the carbonyl functionality through hydrosilylation: Integrating click catalysis with hydrosilylation in one pot
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Herein we report the chemoselective reduction of the carbonyl functionality via hydrosilylation using a copper(I) catalyst bearing the abnormal N-heterocyclic carbene 1 with low (0.25 mol %) catalyst loading at ambient temperature in excellent yield within a very short reaction time. The hydrosilylation reaction of α,β-unsaturated carbonyl compounds takes place selectively toward 1,2-addition (C=O) to yield the corresponding allyl alcohols in good yields. Moreover, when two reducible functional groups such as imine and ketone groups are present in the same molecule, this catalyst selectively reduces the ketone functionality. Further, 1 was used in a consecutive fashion by combining the Huisgen cycloaddition and hydrosilylation reactions in one pot, yielding a range of functionalized triazole substituted alcohols in excellent yields.
- Roy, Sudipta Raha,Sau, Samaresh Chandra,Mandal, Swadhin K.
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p. 9150 - 9160
(2014/12/11)
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- Nitrite ionic liquid as a new reagent for in situ synthesis of aryl iodides and azides
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A new ionic liquid, 1-methyl-3-(2-[2-(1-methyl-1H-imidazol-3-ium-3-yl)ethyloxy] ethyl)-1H-imidazol-3-ium dinitrite, was synthesized. This ionic liquid was used as a convenient nitrosonium source in diazotization of aryl amines into their corresponding diazonium salts, which were converted into aryl iodides and aryl azides using potassium iodide or sodium azide, respectively. Various aryl amines possessing electron-withdrawing groups or electron-donating groups were converted into the corresponding aryl iodides and aryl azides in excellent yields. Advantages of this methodology are the use of mild reaction conditions, short reaction times, and avoiding the use of toxic solvents.
- Eshghi, Hossein,Bakavoli, Mehdi,Ghasemzadeh, Marjan
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p. 3999 - 4007
(2015/06/08)
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- One-pot chemoenzymatic synthesis of chiral disubstituted 1,2,3-triazoles in aqueous media
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A one-pot, two-step procedure combining 1,3-dipolar cycloaddition and an enantioselective reduction mediated by Daucus carota (carrot root) is described. The synthesis was accomplished by first employing the biocatalyst followed by a "click" reaction unde
- De Souza De Oliveira, Camila,De Andrade, Kleber Tellini,Omori, Alvaro Takeo
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- Enantioselective synthesis of C-linked spiroacetal-triazoles as privileged natural product-like scaffolds
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The enantioselective synthesis of novel C-linked spiroacetal-triazoles 10 is reported. The key step involves reaction of acetylenic spiroacetal 11 with several azides by the Copper-Catalysed Azide-Alkyne Cycloaddition (CuAAC). The biologically privileged spiroacetal scaffold 11 was prepared from silyl-protected Weinreb amide 19 using several reliable Grignard additions and a highly diastereoselective enzymatic kinetic resolution.
- Kueh, Jui Thiang Brian,Choi, Ka Wai,Brimble, Margaret A.
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supporting information; experimental part
p. 5993 - 6002
(2012/08/27)
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- Photophysical and photochemical investigations on triazole ring linked chalcone containing polymethacrylates
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A series of polymethacrylates containing triazole ring linked chalcone were designed and synthesized. These conjugated chalcone polymers are modulate under the light depending on the pendant substituents (-N(CH3) 2, CH3, O
- Balamurugan,Nithyanandan,Selvarasu,Yeap,Kannan
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p. 4104 - 4111
(2012/10/29)
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- One-pot, efficient, and regioselective syntheses of 1,4-disubstituted 1,2,3-triazoles using aryldiazonium silica sulfates in water
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A one-pot, efficient, and straightforward procedure for the copper-catalyzed synthesis of 1,4-disubstituted 1,2,3-triazoles is studied by in situ generation of aryl azides via the reaction of aryldiazonium silica sulfates and sodium azide, followed by coupling with a terminal alkyne. These reactions are carried out in water at room temperature without using any additional ligands.
- Zarei, Amin
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experimental part
p. 5176 - 5179
(2012/09/22)
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- Rhodium-catalyzed direct C-H amination of benzamides with aryl azides: A synthetic route to diarylamines
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No muss, no fuss: A rhodium-catalyzed direct intermolecular C-H amination of benzamides and ketoximes using aryl azides as the amine source has been developed. The reaction exhibits a broad substrate scope with excellent functional-group tolerance, requires no external oxidants, releases N 2 as the only by-product, and produces diarylamines in high yields. Copyright
- Ryu, Jaeyune,Shin, Kwangmin,Park, Sae Hume,Kim, Ji Young,Chang, Sukbok
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supporting information
p. 9904 - 9908
(2012/10/29)
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- Microwave-assisted click chemistry synthesis of 1,2,3-triazoles from aryldiazonium silica sulfates in water
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A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles is studied by in situ generation of aryl azides via the reaction of aryldiazonium silica sulfates and sodium azide, followed by coupling with a terminal alkyne in the presence of copper catalyst. These reactions are carried out in water under mild and heterogeneous conditions without using any additional ligands.
- Zarei, Amin,Khazdooz, Leila,Hajipour, Abdol R.,Azizi, Ghobad,Aghaei, Hamidreza
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p. 3353 - 3360,8
(2012/12/12)
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- Direct synthesis of organic azides from primary amines with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate
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Organic azides were prepared from primary amines in high yields by metal-free diazo transfer with 2-azido-1,3-dimethylimidazolinium hexafluorophosphate, which is a stable, crystalline solid that is easy to handle. Organic azides were prepared from primary
- Kitamura, Mitsuru,Yano, Masakazu,Tashiro, Norifumi,Miyagawa, Satoshi,Sando, Mitsuyoshi,Okauchi, Tatsuo
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experimental part
p. 458 - 462
(2011/03/18)
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- Targeting glycolysis: A fragment based approach towards bifunctional inhibitors of hLDH-5
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hLDH-5 has emerged as a promising target for anti-glycolytic cancer chemotherapy. Here we report a first generation of bifunctional inhibitors, which show promising activity against hLDH-5.
- Moorhouse, Adam D.,Spiteri, Christian,Sharma, Pallavi,Zloh, Mire,Moses, John E.
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supporting information; experimental part
p. 230 - 232
(2011/03/22)
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- Copper(II)-catalyzed conversion of aryl/heteroaryl boronic acids, boronates, and trifluoroborates into the corresponding azides: Substrate scope and limitations
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We report the copper(II)-catalyzed conversion of organoboron compounds into the corresponding azide derivatives. A systematic series of phenylboronic acid derivatives is evaluated to examine the importance of steric and electronic effects of the sub-stituents on reaction yield as well as functional group compatibility. Heterocyclic substrates are also shown to participate in this mild reaction while compounds incorporating B-C(sp3) bonds are unreactive under the reaction conditions. The copper(II)-catalyzed boronic acid-azide coupling reaction is further extended to both boronate esters and potassium organotrifluoroborate salts. The method described herein complements existing procedures for the preparation of aryl azides from the respective amino, triazene, and halide derivatives and we expect that it will greatly facilitate copper- and ruthenium-catalyzed azide-alkyne cycloaddition reactions for the preparation of diversely functionalized 1-aryl- or 1-heteroaryl-1,2,3- triazoles derivatives. Georg Thieme Verlag Stuttgart.
- Grimes, Kimberly D.,Gupte, Amol,Aldrich, Courtney C.
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experimental part
p. 1441 - 1448
(2010/10/03)
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- Unsupported copper nanoparticles in the 1,3-dipolar cycloaddition of terminal alkynes and azides
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Readily prepared copper nanoparticles were found to catalyse the 1,3-dipolar cycloaddition of azides and alkynes up to rates comparable to those of microwave chemistry. Both the preparation of the nanoparticles and the click reaction are carried out under mild conditions, in short reaction times and in the absence of any stabilising additive or ligand. A variety of 1,2,3-triazoles were prepared in excellent yields. A reaction mechanism was postulated on the basis of different reactivity studies and deuteration experiments. Copper(I) acetylides were demonstrated to be the real intermediate species.
- Alonso, Francisco,Moglie, Yanina,Radivoy, Gabriel,Yus, Miguel
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supporting information; experimental part
p. 1875 - 1884
(2010/07/18)
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- Highly efficient and safe procedure for the synthesis of aryl 1,2,3-triazoles from aromatic amine in a continuous flow reactor
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The Letter reports a safe and reliable synthesis of aryl 1,2,3-triazoles from the corresponding anilines via intermediate aryl azides, using a continuous process. The method was applied to a variety of substrates with good to excellent yields, without the
- Stazi, Federica,Cancogni, Damiano,Turco, Lucilla,Westerduin, Pieter,Bacchi, Sergio
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supporting information; experimental part
p. 5385 - 5387
(2010/11/02)
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- Reliable and diverse synthesis of aryl azides through copper-catalyzed coupling of boronic acids or esters with TMSN3
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(Figure Presented) Aryl azide formation: The copper-catalyzed coupling reaction of boronic esters and acids with TMSN3 have been presented as a highly efficient, simple, broadly applicable, and less hazardous methodology for the practi cal synthesis of aryl azides with structural diversity (see scheme).
- Li, Yu,Gao, Lian-Xun,Han, Fu-She
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supporting information; experimental part
p. 7969 - 7972
(2010/09/14)
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- A fast and efficient method for the preparation of aryl azides using stable aryl diazonium silica sulfates under mild conditions
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An efficient, fast, and straightforward procedure for the synthesis of aromatic azides using aryl diazonium silica sulfates and sodium azide at room temperature under mild conditions is described. The use of inexpensive materials, simple and clean work-up
- Zarei, Amin,Hajipour, Abdol R.,Khazdooz, Leila,Aghaei, Hamidreza
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experimental part
p. 4443 - 4445
(2009/11/30)
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- Efficient conversion of aromatic amines into azides: A one-pot synthesis of triazole linkages
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An efficient and improved procedure for the preparation of aromatic azides and their application in the Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition ("click reaction") is described. The synthesis of aromatic azides from the corresponding amies i
- Barral, Karine,Moorhouse, Adam D.,Moses, John E.
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p. 1809 - 1811
(2008/02/02)
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- Radical reduction of aromatic azides to amines with triethylsilane
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Aromatic azides are inert toward triethylsilane under thermal conditions in the presence of a radical initiator, but in the presence of additional catalytic amounts of tert-dodecanethiol, they afford anilinosilanes and thence the corresponding anilines in virtually quantitative yields.
- Benati, Luisa,Bencivenni, Giorgio,Leardini, Rino,Minozzi, Matteo,Nanni, Daniele,Scialpi, Rosanna,Spagnolo, Piero,Zanardi, Giuseppe
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p. 5822 - 5825
(2007/10/03)
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- Simple conversion of aromatic amines into azides
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(Matrix presented) A straightforward and highly efficient synthesis of aromatic azides from the corresponding amines is accomplished using triflyl azide under mild conditions.
- Liu, Qi,Tor, Yitzhak
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p. 2571 - 2572
(2007/10/03)
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- Progestin 16α,17α-dioxolane ketals as molecular probes for the progesterone receptor: Synthesis, binding affinity, and photochemical evaluation
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Chemical probes for steroid receptors have proven useful in providing molecular details about important hormone-receptor interactions. A series of progestin 16α,17α-dioxolane ketals of acetophenone or substituted acetophenones that bind to the progesterone receptor (PgR) with comparable or higher affinities than the natural ligand, progesterone, have been prepared and evaluated as potential in vitro and in vivo probes for the progesterone receptor. p-Azidoacetophenone ketal 6, the tetrafluoro analog 8, and the p- (benzoyl)acetophenone ketal 9 demonstrate the required combination of high relative binding affinity (RBA) (6 = 15%, 8 = 14%, 9 = 6.6%, progesterone = 13%, R5020 = 100%) and photoinactivation efficiency (6 = 80%, 8 = 77%, 9 = 29% at 30 min) required for potential photoaffinity labeling reagents for the PgR. The synthesis of azide 6 has been modified to accommodate a palladium- catalyzed tritium gas hydrogenolysis of an iodoaryl precursor in the final stage of the synthetic sequence; this procedure has been verified by hydrogenation. In addition, the progestin p-fluoroacetophenone ketal 10 was selected for preparation in fluorine-18-labeled form, on the basis of its high affinity for the PgR (RBA = 53%). Fluorine-18-labeled progestins may be evaluated as potential diagnostic imaging agents for PgR-positive breast tumors. The radiochemical syntheses and further biochemical results with the fluorine-18-labeled ketal 10 and the tritium-labeled aryl azide 6 will be presented in an accompanying paper and elsewhere.
- Kym,Carlson,Katzenellenbogen
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p. 1111 - 1119
(2007/10/02)
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- Superoxide dismutase-like activity of 1,2,3-triazole derivatives.
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This paper reports the synthesis of some sulfurated 1,2,3-triazole derivatives and the biological evaluation, for the superoxide dismutase-like activity, of these new compounds together with several 1,2,3-triazoles previously described by us. All the compounds possess a SOD-like activity and some of them showed an activity equivalent to or higher than those of penicillamine or thiopronin, which are well known therapeutic drugs in the treatment of rheumatoid arthritis.
- Biagi,Livi,Ramacciotti,Scartoni,Bazzichi,Mazzoni,Lucacchini
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