- Copper-Catalyzed Azide-Alkyne Cycloaddition of Hydrazoic Acid Formed in Situ from Sodium Azide Affords 4-Monosubstituted-1,2,3-Triazoles
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We report a copper-catalyzed cycloaddition of hydrogen azide (hydrazoic acid, HN3) with terminal alkynes to form 4-substituted-1H-1,2,3-triazoles in a sustainable manner. Hydrazoic acid was formed in situ from sodium azide under acidic conditions to react with terminal alkynes in a copper-catalyzed reaction. Using polydentate N-donor chelating ligands and mild organic acids, the reactions were realized to proceed at room temperature under aerobic conditions in a methanol-water mixture and with 5 mol % catalyst loadings to afford 4-substituted-1,2,3-triazoles in high yields. This method is amenable on a wide range of alkyne substrates, including unprotected peptides, showing diverse functional group tolerance. It is applicable for late-stage functionalization synthetic strategies, as demonstrated in the synthesis of the triazole analogue of losartan. The preparation of orthogonally protected azahistidine from Fmoc-l-propargylglycine was realized on a gram scale. The hazardous nature of hydrazoic acid has been diminished as it forms in situ in a reactive species in the copper-catalyzed reaction.
- Jankovi?, Dominik,Virant, Miha,Gazvoda, Martin
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p. 4018 - 4028
(2022/02/25)
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- Direct Synthesis of 4-Aryl-1,2,3-triazoles via I2-Promoted Cyclization under Metal- And Azide-Free Conditions
-
We herein report an iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved
- Geng, Xiao,Huang, Chun,Wang, Li-Sheng,Wu, An-Xin,Wu, Yan-Dong,Yu, Xiao-Xiao,Zhao, Peng,Zhou, You
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p. 13664 - 13672
(2021/10/01)
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- Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis
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Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.
- Bai, Rongxian,Gao, Feng,Gu, Yanlong,Li, Minghao
-
supporting information
p. 7499 - 7505
(2021/10/12)
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- Silica immobilized copper N-heterocyclic carbene: An effective route to 1,2,3-triazoles via azide-alkyne cycloaddition and multicomponent click reaction
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A new silica supported copper N-heterocyclic carbene (Cu-NHC@SiO2) complex is prepared and characterized by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and X-ray photoelectron spectroscopy (XPS) analyses. This complex is an efficient and easily retrievable catalyst for 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition reaction as well as one-pot reaction using arylboronic acids. This catalytic system is also suitable for synthesis of 4-aryl-NH-1,2,3-triazoles from diverse benzaldehydes. Further, the catalyst can efficiently be recycled up to fifth cycle for all the three methods of 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition and multi-component reactions.
- Garg, Anirban,Borah, Nobomi,Sultana, Jasmin,Kulshrestha, Akshay,Kumar, Arvind,Sarma, Diganta
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-
- Access to (Z)-β-Substituted Enamides from N1-H-1,2,3-Triazoles
-
A direct ring-opening/nucleophilic substitution reaction of N1-H-1,2,3-triazoles has been described. Divergent (Z)-β-halogen- or sulfonyl-substituted enamides could be stereospecifically synthesized in a tunable manner. This strategy might not only enable
- Wang, Tao,Tang, Zongyuan,Luo, Han,Tian, Yi,Xu, Mingchuan,Lu, Qixing,Li, Baosheng
-
supporting information
p. 6293 - 6298
(2021/08/23)
-
- Sulfonic acid-functionalized magnetic carbon nitride as highly efficient ionic composite for sustainable assembly of 1,2,3-triazoles
-
Abstract: An efficient and straightforward method for constructing of biologically active 4-aryl-NH-1,2,3-triazoles by the 1,3-dipolar cycloaddition reaction of β-nitrostyrene?and sodium azide in the presence of acidic graphitic carbon nitride (Fe3/
- Saadat, Mostafa,Azizi, Najmedin,Qomi, Mahnaz
-
p. 2057 - 2064
(2021/02/01)
-
- A green metal-free "one-pot" microwave assisted synthesis of 1,4-dihydrochromene triazoles
-
The synthesis of several 4-aryl-1,4-dihydrochromene-triazoles was achieved via a metal-free "one-pot"procedure using PEG400 as the sole solvent in an eco-friendly process. Using microwave irradiation, the triazole derivatives were obtained in good yields and short reaction times starting from readily accessible building blocks.
- Alves, Tania M. F.,Jardim, Guilherme A. M.,Ferreira, Marco A. B.
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p. 10336 - 10339
(2021/03/26)
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- Iodine-Mediated Condensation–Cyclization of α-Azido Ketones with p-Toluenesulfonyl Hydrazide for Synthesis of 4-Aryl-NH-1,2,3-Triazoles
-
A molecular iodine mediated condensation–cyclization reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed from readily available α-azido acetophenones and p-toluenesulfonyl hydrazide. This reaction provides a metal-free strategy for the sequential formation of C–N and N–N bonds in mild condition.
- Ren, Ming-Tian,Li, Min,Wang, An-Jing,Gao, Jie,Zhang, Xiang-Xiang,Shu, Wen-Ming
-
supporting information
p. 2233 - 2236
(2020/04/16)
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- Cu-Catalyzed Site-Selective and Enantioselective Ring Opening of Cyclic Diaryliodoniums with 1,2,3-Triazoles
-
A Cu-catalyzed enantioselective ring-opening/triazolylation reaction is reported. The reaction shows excellent chemoselectivity regarding the three different nitrogen atoms of 1,2,3-triazoles. The optically enriched axially chiral aryl iodides thus obtained were readily derivatized to different types of chiral phosphine ligands and their corresponding copper or palladium complexes.
- Chao, Zengyin,Ma, Mingming,Gu, Zhenhua
-
supporting information
p. 6441 - 6446
(2020/09/02)
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- Metal-Free Cascade [4 + 1] Cyclization Access to 4-Aryl- NH-1,2,3-triazoles from N-Tosylhydrazones and Sodium Azide
-
A molecular iodine-mediated coupling cyclization reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed from N-tosylhydrazones and sodium azide. This metal-free cascade [4 + 1] cyclization reaction could rapidly synthesize valuable com
- Shu, Wen-Ming,Zhang, Xun-Fang,Zhang, Xiang-Xiang,Li, Min,Wang, An-Jing,Wu, An-Xin
-
p. 14919 - 14925
(2019/11/11)
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- Sulfated tungstate a heterogeneous acid catalyst for synthesis of 4-aryl-NH-1,2,3-triazoles by 1,3-dipolar cycloaddition of nitroolefins with NaN3
-
A facile and new method for the synthesis of 4-aryl-NH-1,2,3-triazoles from nitroolefins and NaN3 by 1,3-dipolar cycloaddition reaction, employing a mild solid inorganic acid sulfated tungstate as a heterogeneous catalyst, has been developed. T
- Autade, Snehalata B.,Akamanchi, Krishnacharya G.
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p. 1947 - 1956
(2019/05/17)
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- Facile Synthesis of 1,3,5-Triarylbenzenes and 4-Aryl-NH-1,2,3-Triazoles Using Mesoporous Pd-MCM-41 as Reusable Catalyst
-
We report mesoporous nano-Pd-MCM-41 catalyzed rapid and efficient synthesis of 1,3,5-triarylbenzenes via de-nitrative cyclotrimerization of β-nitrostyrenes. All the reactions were very fast and high yielding. The Pd-MCM-41 was also very effective in catalyzing de-nitrative [3+2] cycloaddition of β-nitrostyrenes with TMSN3 to synthesize 4-aryl-NH-1,2,3-triazoles. The catalyst was reused at least up to eight times with minimum loss of catalytic activity.
- Saha, Arijit,Wu, Chia-Ming,Peng, Rui,Koodali, Ranjit,Banerjee, Subhash
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p. 104 - 111
(2019/01/04)
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- Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety
-
The Cu(I)- or Ag(I)-catalyzed cycloaddition between 8-ethynyladenine or guanine nucleosides and TMSN3 gave 8-(1-H-1,2,3-triazol-4-yl) nucleosides in good yields. On the other hand, reactions of 5-ethynyluracil or cytosine nucleosides with TMSN3 led to the chemoselective formation of triazoles via Cu(I)-catalyzed cycloaddition or vinyl azides via Ag(I)-catalyzed hydroazidation. These nucleosides with a minimalistic triazolyl modification showed excellent fluorescent properties with 8-(1-H-1,2,3-triazol-4-yl)-2′-deoxyadenosine (8-TrzdA), exhibiting a quantum yield of 44%. The 8-TrzdA 5′-triphosphate was incorporated into duplex DNA containing a one-nucleotide gap by DNA polymerase β.
- Wen, Zhiwei,Tuttle, Paloma R.,Howlader, A. Hasan,Vasilyeva, Anna,Gonzalez, Laura,Tangar, Antonija,Lei, Ruipeng,Laverde, Eduardo E.,Liu, Yuan,Miksovska, Jaroslava,Wnuk, Stanislaw F.
-
-
- A mineralogically-inspired silver-bismuth hybrid material: An efficient heterogeneous catalyst for the direct synthesis of nitriles from terminal alkynes
-
The synthesis and characterization of a silver-containing hybrid material is reported as a novel heterogeneous noble metal catalyst. In order to eliminate the need for traditional immobilization techniques, and to create a solid material with structurally-bound silver catalytic centers, the layered structure of a naturally occurring mineral served as the basis of the initial catalyst design. The novel material was prepared by means of the urea-mediated homogeneous precipitation of the corresponding metal nitrates, and was fully characterized by means of diverse instrumental techniques (X-ray diffractometry, Raman, IR, UV-Vis, EPR, X-ray photoelectron spectroscopies, thermal methods as well as atomic force, scanning and transmission electron microscopies). The as-prepared material exhibited outstanding activity in silver-catalyzed CC bond activation to yield organic nitriles directly from terminal alkynes with less environmental concerns as compared to the classical synthesis methods. The effects of the reaction time, the temperature, as well as the role of various solvents, nitrogen sources and additives were carefully scrutinized in order to achieve high-yielding and selective nitrile formation. The heterogeneous nature of the reaction was verified and the solid catalyst was recycled and reused numerous times without loss of its activity or degradation of its structure, thereby offering a sustainable synthetic methodology.
- ?tv?s, Sándor B.,Mészáros, Rebeka,Varga, Gábor,Kocsis, Marianna,Kónya, Zoltán,Kukovecz, ákos,Pusztai, Péter,Sipos, Pál,Pálinkó, István,Fül?p, Ferenc
-
p. 1007 - 1019
(2018/03/13)
-
- Copper(I)-Catalyzed Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Azidoformates and Aryl Terminal Alkynes
-
The copper(I)-catalyzed azide-alkyne cycloaddition reaction has been extensively studied and widely applied in organic synthesis. However, the formation of 1,2,3-triazoles with electron-deficient azide has been a challenging problem. In this report, we ha
- Lee, Heejin,Lee, Jae Kyun,Min, Sun-Joon,Seo, Hyeonglim,Lee, Youngbok,Rhee, Hakjune
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p. 4805 - 4811
(2018/04/26)
-
- Magnetically recoverable copper ferrite catalyzed cascade synthesis of 4-Aryl-1H-1,2,3-triazoles under microwave irradiation
-
Magnetically active CuFe2O4 catalyzed cascade synthesis of 4-Aryl-1H-1,2,3-triazoles under microwave irradiation starting from aromatic aldehydes, sodium azide and nitromethane has been developed and demonstrated here. The catalyst system needed for the purpose was prepared following a procedure by A. Dandiya et al. with a slight modification and was characterized using FT-IR, XRD, SEM-EDX and TEM analysis. The most notable advantage of the developed methodology is the excellent time economy to carry out the transformation. Other features include simple operating procedure, wide substrate coverage and easy recovery of the catalyst. Reusability of the catalyst has been tested and found to be very satisfactory up to sixth cycle without significant loss in efficiency. All the synthesized compounds have been characterized using FTIR, 1H & 13CNMR spectroscopy, HRMS.
- Bhuyan, Pubanita,Bhorali, Pratiksha,Islam, Imdadul,Bhuyan, Amar Jyoti,Saikia, Lakhinath
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p. 1587 - 1591
(2018/03/29)
-
- Sulfonation of carbonized xylan-type hemicellulose: A renewable and effective biomass-based biocatalyst for the synthesis of O- and N-heterocycles
-
The application of biomass-based carbonaceous solid acids in catalysis is attracting increasing attention in the field of chemistry. In this study, a heterogeneous carbon-based solid acid biocatalyst (CXH-SO3H) with regular spherical structure was synthesized from xylan-type hemicellulose (XH) by a simple two-step method. The catalyst was successfully applied in the synthesis of O- and N-heterocycles with yields of 80-99% and 60-97%, respectively. In view of environment and economy, CXH-SO3H shows the merits of environmental friendliness, easy operation, simple work-up, excellent yields, and the avoidance of use of organic solvents and expensive catalysts. Moreover, the as-synthesized solid acid catalyst could be used for several cycles without significant loss in its catalytic activity. The results of FT-IR, XRD, and SEM showed that no distinct differences in physico-chemical structures of CXH-SO3H were observed. Thus, the eco-friendly CXH-SO3H catalyst is a promising candidate for green synthesis of O- and N-heterocycles from low-cost feed-stocks and has good prospect in partially substituting commercially available solid and liquid acid catalysts and precious metal catalysts.
- Ma, Jiliang,Peng, Xinwen,Zhong, Linxin,Sun, Runcang
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p. 9140 - 9150
(2018/06/11)
-
- On Water Cu@g-C3N4 Catalyzed Synthesis of NH-1,2,3-Triazoles via [2+3] Cycloadditions of Nitroolefins/Alkynes and Sodium Azide
-
Here, we have reported fabrication of graphitic polymeric C3N4 supported CuCl2 (Cu@g-C3N4) and characterized by powder X-ray diffraction, field emission scanning electron microscopy, high resolution transmission electron microscopy, X-ray photoelectron spectroscopy studies. An efficient and regioselective protocol for the on water synthesis of 4-aryl-NH-1,2,3-triazole derivatives via 1,3-diipolar cycloaddition reactions of nitroolefins/phenylacetylenes to sodium azide were demonstrated by using Cu@g-C3N4 as robust and reusable catalyst.
- Payra, Soumen,Saha, Arijit,Banerjee, Subhash
-
p. 5468 - 5474
(2018/11/23)
-
- Method of catalytically synthesizing 4-aryl-NH-1,2,3-triazole derivative under microwave radiation
-
The invention discloses a method of catalytically synthesizing 4-aryl-NH-1,2,3-triazole derivative under microwave radiation. The method includes the steps of: successively adding substituted 2-nitroolefin, sodium azide, TfOH, and pyridine into a reaction
- -
-
Paragraph 0011; 0028
(2018/03/26)
-
- One-Pot Synthesis of 4-Aryl-NH-1,2,3-Triazoles through Three-Component Reaction of Aldehydes, Nitroalkanes and NaN3
-
A one-pot three-component reaction of aldehydes, nitroalkanes and NaN3 for the synthesis of NH-1,2,3-triazoles has been developed. The reaction provides a safe, efficient and step-economic approach for the synthesis of various NH-1,2,3-triazoles in good to excellent yields.
- Hui, Rongrong,Zhao, Mina,Chen, Ming,Ren, Zhihui,Guan, Zhenghui
-
p. 1808 - 1812
(2017/09/06)
-
- Synthesis of N-unsubstituted 1,2,3-triazoles via aerobic oxidative N-dealkylation using copper(II) acetate
-
A copper-catalyzed aerobic oxidative C[sbnd]N bond cleavage reaction was developed for the synthesis of 4-substituted-NH-1,2,3-triazoles. Diverse β-ketotriazoles derivatives, which are the starting materials for the aerobic oxidative C[sbnd]N bond cleavage reaction, were prepared from nine aryl and seven alkyl alkynes and α-azidoacetophenone by a copper(I)-catalyzed [3?+?2]cycloaddition reaction. The aerobic oxidation of α-(1,2,3-triazol-1-yl)acetophenones using a catalytic amount of copper(II) acetate in the presence oxygen under neutral conditions gave the title compounds in high yield.
- Cha, Hyojin,Lee, Kyongkyu,Chi, Dae Yoon
-
p. 2878 - 2885
(2017/04/26)
-
- ZrCl4-mediated synthesis of 1,2,3-triazoles from vinyl nitrates and their biological evaluation
-
A ZrCl4-mediated simple method for the conversion of vinyl nitrates to 1,2,3-triazoles in excellent yields is developed. The obtained new triazoles were evaluated for their antimicrobial activity.
- Sridhar, Gattu,Somnath, Mudavath,Sharma, Gangavaram V. M.,Prashanth, Thodupunuri
-
p. 551 - 556
(2017/03/15)
-
- DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles
-
Aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to 2-cycloalken-1-ones has been studied in the presence of DABCO as organic base. The reactions were carried out in acetonitrile at room temperature to provide 2,4-disubstituted 2H-1,2,3-triazoles as major
- Bhagat, Ujjawal Kumar,Kamaluddin,Peddinti, Rama Krishna
-
supporting information
p. 298 - 301
(2017/01/03)
-
- ANTI-ENTEROVIRUS 71 THIADIAZOLIDINE DERIVATIVE
-
Disclosed is a novel anti-enterovirus 71 (EV71) 1,2,5-thiadiazolidine-1,1-dioxide derivative or a pharmaceutically acceptable salt thereof; and specifically, a compound represented by formula (II) or a pharmaceutically acceptable salt thereof.
- -
-
Paragraph 0525-0526
(2017/03/28)
-
- Synthesis method of NH-1,2,3-triazole compound
-
The invention relates to a synthesis method of a NH-1,2,3-triazole compound. The synthesis method is characterized by comprising the following steps that aldehyde, a nitro compound, sodium azide, a solvent and an additive react for 1-8 hours through a one-pot method at the temperature of 80 DEG C to 150 DEG C, and after reacting is finished, NH-1,2,3-triazole can be prepared through aftertreatment. According to the synthesis method, aldehyde, the nitro compound and sodium azide which are cheap and easy to obtain are adopted as raw materials, and the NH-1,2,3-triazole compound can be conveniently prepared from the three components. Compared with an existing method, the method has the advantages that the raw materials are low in cost, simple and easy to obtain, operation is easy and convenient, and the reaction efficiency is high.
- -
-
Paragraph 0020
(2017/07/20)
-
- 4-Aryl- NH -1,2,3-Triazoles via Multicomponent Reaction of Aldehydes, Nitroalkanes, and Sodium Azide
-
4-Aryl-NH-1,2,3-triazoles are valuable compounds in organic chemistry and pharmaceutical chemistry. In this paper, we describe a novel multicomponent reaction of aldehydes, nitroalkanes, and sodium azide for the synthesis of 4-aryl-NH-1,2,3-triazoles. In this transformation, it was found that both the slow addition of nitroalkane and the presence of NaHSO3/Na2SO3 are advantageous to promote the reaction results. Additionally, a series of aldehydes and nitro compounds were investigated.
- Wu, Luyong,Wang, Xianghui,Chen, Yuxue,Huang, Qinglan,Lin, Qiang,Wu, Mingshu
-
p. 437 - 441
(2016/02/09)
-
- A single-step acid catalyzed reaction for rapid assembly of: NH -1,2,3-triazoles
-
NH-1,2,3-Triazole moieties are a part of the design of various biologically active compounds, pharmaceutical agents and functional materials. Unfortunately, the applications of this heterocycle are still underexplored due to the lack of a general synthetic protocol. Here we outline a novel, general and facile metal-free pathway that enables the direct synthesis of these heterocycles by combining readily accessible and abundant precursors such as enolizable ketones and NH4OAc with high levels of regioselectivity via an organocascade process. The developed chemistry has been successfully applied to the synthesis of several structurally diverse products, pharmaceutical agents and supramolecular receptors.
- Thomas, Joice,Jana, Sampad,Liekens, Sandra,Dehaen, Wim
-
supporting information
p. 9236 - 9239
(2016/07/25)
-
- Water-soluble NHC-Cu catalysts: Applications in click chemistry, bioconjugation and mechanistic analysis
-
Copper(i)-catalyzed 1,3-dipolar cycloaddition of azides and terminal alkynes (CuAAC), better known as "click" reaction, has triggered the use of 1,2,3-triazoles in bioconjugation, drug discovery, materials science and combinatorial chemistry. Here we report a new series of water-soluble catalysts based on N-heterocyclic carbene (NHC)-Cu complexes which are additionally functionalized with a sulfonate group. The complexes show superior activity towards CuAAC reactions and display a high versatility, enabling the production of triazoles with different substitution patterns. Additionally, successful application of these complexes in bioconjugation using unprotected peptides acting as DNA binding domains was achieved for the first time. Mechanistic insight into the reaction mechanism is obtained by means of state-of-the-art first principles calculations.
- Daz Velzquez, Heriberto,Ruiz Garca, Yara,Vandichel, Matthias,Madder, Annemieke,Verpoort, Francis
-
supporting information
p. 9350 - 9356
(2014/12/11)
-
- Copper-catalyzed synthesis of 4-Aryl-1H-1,2,3-triazoles from 1,1-dibromoalkenes and sodium azide
-
A new methodology for the Cu-catalyzed synthesis of 1H-1,2,3-triazoles from 1,1-dibromoalkenes and sodium azide is presented. Aryl dibromoolefins were efficiently converted into the corresponding 1,2,3-triazoles. A comprehensive number of functional group
- Wang, Xiaokun,Kuang, Chunxiang,Yang, Qing
-
experimental part
p. 424 - 428
(2012/02/03)
-
- Preparation of reusable Ag-decorated graphene oxide catalysts for decarboxylative cycloaddition
-
In this study, we demonstrated a noble Ag-decorated graphene oxide catalyst (GOSH-Ag) for use in the decarboxylative cycloaddition reaction. The catalyst was easily prepared by depositing Ag nanoparticles on thiolated graphene oxide (GOSH) surfaces. Trans
- Kim, Ji Dang,Palani, Thiruvengadam,Kumar, Manian Rajesh,Lee, Sunwoo,Choi, Hyun Chul
-
p. 20665 - 20670
(2013/02/22)
-
- Structure-activity relationship and enzyme kinetic studies on 4-aryl-1H-1,2,3-triazoles as indoleamine 2,3-dioxygenase (IDO) inhibitors
-
Previously, we have reported the design and synthesis of 4-aryl-1H-1,2,3-triazoles as inhibitors of indoleamine 2,3-dioxygenase (IDO), a promising therapeutic target of cancer. Here, we present the structure-activity relationship and enzyme kinetic studie
- Huang, Qiang,Zheng, Maofa,Yang, Shuangshuang,Kuang, Chunxiang,Yu, Cunjing,Yang, Qing
-
scheme or table
p. 5680 - 5687
(2011/12/16)
-
- Traceless azido linker for the solid-phase synthesis of N H-1,2,3-triazoles via Cu-catalyzed azide - Alkyne cycloaddition reactions
-
A broadly useful acid-labile traceless azido linker for the solid-phase synthesis of NH-1,2,3-triazoles is presented. A variety of alkynes were efficiently immobilized on a range of polymeric supports by Cu(I)-mediated azide - alkyne cycloadditions. Suppo
- Cohrt, A. Emil,Jensen, Jakob F.,Nielsen, Thomas E.
-
supporting information; experimental part
p. 5414 - 5417
(2011/03/19)
-
- Acid-catalyzed synthesis of 10-substituted triazolyl artemisinins and their growth inhibitory activity against various cancer cells
-
A diastereomeric and regioisomeric library of 10-substituted triazolyl artemisinin compounds (6a-6h, 7a-7h, and 8a-8h) with a potent growth inhibitory activities against various cancer cell lines was established. These compounds were synthesized by a reaction with dihydroartemisinin (2) and various substituted triazoles (5a-5h) in methylene chloride using a BF3Et2O catalyst. Most of the compounds exhibited a strong potency in the submicromolar range, and, in particular, 6f, 7f, and 8f, which have a pentylphenyltriazole moiety, proved to be promising candidates for preclinical trials.
- Oh, Sangtae,Shin, Woon-Seob,Ham, Jungyeob,Lee, Seokjoon
-
scheme or table
p. 4112 - 4115
(2010/09/04)
-
- N-substituted-1,2,3-triazoles: Synthesis, characterization and evaluation as cannabinoid ligands
-
A series of new N1-, N2-and N3-substituted 1,2,3-triazole derivatives has been synthesized by cycloaddition of butyltin azide with substituted alkynes followed by a N-alkylation reaction. The regioisomers have been isolated and characterized using NMR tec
- Oliva, Cristina G.,Jagerovic, Nadine,Goya, Pilar,Alkorta, Ibon,Elguero, Jose,Cuberes, Rosa,Dordal, Alberto
-
experimental part
p. 127 - 147
(2010/08/04)
-
- Bitriazolyl acyclonucleosides with antiviral activity against tobacco mosaic virus
-
Bitriazolyl acyclonucleosides were synthesized via the Huisgen reaction and then subjected to ammonolysis. The antiviral activity of these nucleosides against tobacco mosaic virus (TMV) was assessed. Like the previously described bitriazolyl compounds, th
- Li, Wei,Xia, Yi,Fan, Zhijin,Qu, Fanqi,Wu, Qiongyou,Peng, Ling
-
p. 2804 - 2809
(2008/09/19)
-
- Preparation of 1H-1,2,3-triazoles by cuprous ion mediated cycloaddition of terminal alkyne and sodium azide
-
1H-1,2,3-triazoles can be prepared in good yield by the reaction of terminal alkyne and sodium azide in the presence of cuprous chloride at a temperature higher than 70 °C. The alkyne is unactivated and the reaction has to be carried out under inert gas.
- Lu, Li-Hui,Wu, Jia-Hao,Yang, Chia-Hsi
-
p. 414 - 417
(2008/12/22)
-
- 1,2,3-Triazole derivatives as cannabinoid-receptor modulators
-
The invention relates to the use of compounds having pharmacological activity towards the so-called cannabonid receptors, and more particularly to some 1,2,3-triazole derivatives of formula (I): to processes of preparation of such compounds and to pharmac
- -
-
Page/Page column 11
(2008/12/05)
-
- Developments in Pd catalysis: Synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides
-
Another star for the Palladium: The discovery of reactions promoted by the ubiquitous Pd0 catalysts is still possible. 1H-1,2,3-Triazoles are directly obtained by reaction of alkenyl bromides and sodium azide in the presence of a Pd0-xantphos catalyst (see scheme, xantphos = 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene, dba = trans,trans- dibenzylideneacetone). (Chemical Equation Presented).
- Barluenga, Jose,Valdes, Carlos,Beltran, Gustavo,Escribano, Maria,Aznar, Fernando
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p. 6893 - 6896
(2007/10/03)
-
- 4-Aryl-1,2,3-triazole: A novel template for a reversible methionine aminopeptidase 2 inhibitor, optimized to inhibit angiogenesis in vivo
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Inhibitors of human methionine aminopeptidase type 2 (hMetAP2) are of interest as potential treatments for cancer. A new class of small molecule reversible inhibitors of hMetAP2 was discovered and optimized, the 4-aryl-1,2,3-triazoles. Compound 24, a potent inhibitor of cobalt-activated hMetAP2, also inhibits human and mouse endothelial cell growth. Using a mouse matrigel model, this reversible hMetAP2 inhibitor was also shown to inhibit angiogenesis in vivo.
- Kallander, Lara S.,Lu, Qing,Chen, Wenfang,Tomaszek, Thaddeus,Yang, Guang,Tew, David,Meek, Thomas D.,Hofmann, Glenn A.,Schulz-Pritchard, Christina K.,Smith, Ward W.,Janson, Cheryl A.,Ryan, M. Dominic,Zhang, Gui-Feng,Johanson, Kyung O.,Kirkpatrick, Robert B.,Ho, Thau F.,Fisher, Paul W.,Mattern, Michael R.,Johnson, Randall K.,Hansbury, Michael J.,Winkler, James D.,Ward, Keith W.,Veber, Daniel F.,Thompson, Scott K.
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p. 5644 - 5647
(2007/10/03)
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- NH-1,2,3-triazoles from azidomethyl pivalate and carbamates: Base-labile N-protecting groups
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NH-1,2,3-triazoles have been prepared via the copper(I)-catalyzed 1,3-dipolar cycloaddition between terminal alkynes and three N-protected organic azides, azidomethyl pivalate, azidomethyl morpholine-4-carboxylate, and azidomethyl N,N-diethylcarbarnate. T
- Loren, Jon C.,Krasiński, Antoni,Fokin, Valery V.,Sharpless, K. Barry
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p. 2847 - 2850
(2007/10/03)
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- Facile deallylation protocols for the preparation of N-unsubstituted triazoles and tetrazoles
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Two facile deallylation protocols have been developed for the preparation of N-unsubstituted triazoles and tetrazoles. The first protocol is a direct deallylation using a combination of a catalytic amount of nickel complex, NiCl2(dppe), and a stoichiometric amount of Grignard reagent, tBuMgCl. The second protocol is a stepwise deallylation through consecutive reactions of isomerization and ozonolysis. The isomerization from N-allylazoles to N-vinylazoles is catalyzed by a ruthenium complex, HRuCl(CO)(PPh3)3, and the following ozonolysis of the derived N-vinyl intermediates affords N-unsubstituted azoles. These protocols can be used complementarily depending on the type of functional groups in the parent allylated azoles.
- Kamijo, Shin,Huo, Zhibao,Jin, Tienan,Kanazawa, Chikashi,Yamamoto, Yoshinori
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p. 6389 - 6397
(2007/10/03)
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- Copper-catalyzed synthesis of N-unsubstituted 1,2,3-triazoles from nonactivated terminal alkynes
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The [3+2] cycloaddition of nonactivated terminal alkynes and trimethylsilyl azide proceeded smoothly in the presence of CuI catalyst and DMF/MeOH, to give the corresponding N-unsubstituted triazoles in good to high yields. The reaction most pro
- Jin, Tienan,Kamijo, Shin,Yamamoto, Yoshinori
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p. 3789 - 3791
(2007/10/03)
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- Compounds and methods
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Compounds of this invention are non-peptide, reversible inhibitors of type 2 methionine aminopeptidase, useful in treating conditions mediated by angiogenesis, such as cancer, haemangioma, proliferative retinophathy, rheumatoid arthritis, atherosclerotic
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- SYNTHESIS AND PROPERTIES OF 1,2,3-TRIAZOLES THAT CONTAIN A FERROCENYL RING
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Ferrocenesulfonyl azide reacts with a number of aroylmethylenetriphenylphosphinomethylenes in dry methylene chloride to give 1,4,5-trisubstituted 1,2,3-triazoles (61-77percent yields), which are readily converted to 4,5-disubstituted 1,2,3-triazoles and ethyl ferrocenesulfonate when they are refluxed in ethanol.The known triphenylphosphazo ferrocenyl sulfone and ethyl diazoacetate are formed in the case of the reaction of ferrocenesulfonyl azide with carbethoxymethylenetriphenylphosphinomethylene.The structures of the synthesized compounds were proved by the results of elementary analysis and IR, UV, and mass spectroscopy.
- Boev, V. I.,Kushnir, V. N.,Shevchuk, M. I.,Dombrovskii, A. V.
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p. 550 - 552
(2007/10/02)
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