- 1, 4-Diazabicyclo[2.2.2]octane-sulfonic acid immobilized on magnetic Fe3O4?SiO2 nanoparticles: a novel and recyclable catalyst for the one-pot synthesis of 4-aryl-NH-1, 2, 3-triazoles
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Abstract: In this study, the surface of silica-coated magnetic nanoparticles (Fe3O4?SiO2) were successfully functionalized by an organic ligand of 1, 4-Diazabicyclo[2.2.2]octane (DABCO)-sulfonic acid and used as a highly efficient catalyst for the synthesis of 4-aryl-NH-1, 2, 3-triazoles from the benzyl alcohol derivatives, nitromethane and sodium azide in ethanol. Furthermore, this catalyst could be recovered and reused five times without noticeable loss of activity. Graphic Abstract: Fe3O4?SiO2?TCT-DABCO-SO3H nanoparticles were successfully synthesized and used as a novel, recyclable, efficient and heterogeneous catalyst for the synthesis of 4-aryl-NH-1, 2, 3-triazoles.[Figure not available: see fulltext.]
- Bagheri, Sepideh,Heydari, Akbar,Jadidi Nejad, Masoumeh,Pazoki, Farzane,Yazdani, Elahe
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- A Simple Protocol for the Stereoselective Construction of Enaminyl Sulfonyl Fluorides
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A clickable connective hub 1-bromo-2-triazolethane-1-sulfonyl fluoride BTESF (1) was developed and successfully applied for the fluorosulfonylvinylation of a host of primary and secondary cyclic or acyclic amines including amino acids and pharmaceuticals. Further antimicrobial experiments revealed that vinyl sulfonyl fluoride functionalized norfloxacin (3ak), ciprofloxacin (3am), and lomefloxacin (3an) exhibited 4-fold improved antimicrobial activity against Gram-positive bacteria compared to their parent drugs.
- Leng, Jing,Tang, Wenjian,Fang, Wan-Yin,Zhao, Chuang,Qin, Hua-Li
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- Visible-light-mediated C2-amination of thiophenes by using DDQ as an organophotocatalyst
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In this work, a direct C-H activation of thiophenes was presented via an oxidation pathway under visible-light irradiation, in which the thiophene radical cation serves as the key intermediate. Various thiophenes and azoles could be transformed into the corresponding amination products well, and H2O was the only byproduct which is environmentally benign. Our results showed that tert-butyl nitrite (TBN) served as the electron transfer mediator and O2 as the terminal oxidant to regenerate the photocatalyst DDQ and revive the photocatalytic cycle.
- Song, Chunlan,Yi, Hong,Dou, Bowen,Li, Yiying,Singh, Atul K.,Lei, Aiwen
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- Copper-Catalyzed Three-Component Reaction of Alkynes, TMSN3, and Ethers: Regiocontrollable Synthesis of N1- And N2-Oxyalkylated 1,2,3-Triazoles
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A new copper-catalyzed selective synthesis of N1- and N2-oxyalkylated 1,2,3-triazoles has been developed through a three-component reaction of alkynes, TMSN3, and ethers. Through this methodology, a series of N1
- Bao, Pengli,Yue, Huilan,Meng, Na,Zhao, Xiaohui,Li, Jiangsheng,Wei, Wei
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- Efficient, mild synthesis of N-unsubstituted 1,2,3-triazoles from methanolysis of 1-sulfonyl-1,2,3-triazoles
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A small library of diverse N-unsubstituted 1,2,3-triazoles was prepared from the corresponding 1-sulfonyl-1,2,3-triazoles, which were treated only with MeOH at reflux temperature. This process was carried out in good yields showing high efficiency and goo
- Rodríguez-Florencio, Janeth,Martínez-Otero, Diego,García-Eleno, Marco A.,Cuevas-Ya?ez, Erick
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- Recyclable Acid–Base Bifunctional Core–Shell–Shell Nanosphere Catalyzed Synthesis of 5-Aryl-1H-1,2,3-triazoles through the “One-Pot” Cyclization of Aldehydes, Nitromethane, and Sodium Azide
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A magnetically separable core–shell–shell nanosphere, Fe3O4@nSiO2-SO3H@MS-NHCOCH3 (n=nonporous, MS=microporous SiO2), was fabricated as an acid–base collaborative catalyst for the three-component cyclization of aromatic aldehydes, nitroalkane, and sodium azide to afford 1H-1,2,3-triazoles. The bifunctional heterogeneous catalyst showed high activity for this transformation and good chemoselectivity, and toxic HN3 was not released during the course of the reaction. A variety of aldehydes were transformed into the corresponding 5-aryl-1H-1,2,3-triazoles in up to 98 % yield. Furthermore, the catalyst could be recovered by using an external magnetic field and reused many times without any loss in activity. In contrast, a homogeneous catalyst system comprising ammonium acetate/acetic acid also worked in this three-component cyclization to afford 1H-1,2,3-triazoles.
- Liu, Lei,Ai, Yongjian,Li, Dong,Qi, Li,Zhou, Junjie,Tang, Zhike,Shao, Zixing,Liang, Qionglin,Sun, Hong-Bin
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- Highly Regioselective Radical Transformation of N-Sulfonyl-1,2,3-triazoles in Air
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The classic transformations of N-sulfonyl-1,2,3-triazoles were processed via nitrogen anion (hydrolysis, etc.) and carbene intermediates, and no efficient examples via radical intermediates were developed. Here, we reported a catalyst-free radical chain t
- Li, Zi,Wei, Qinghua,Song, Longlong,Han, Wangyujing,Wu, Xiang,Zhao, Yun,Xia, Fei,Liu, Shunying
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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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- Synthesis, DNA-binding abilities and anticancer activities of triazole-pyrrolo[2,1-c][1,4]benzodiazepines hybrid scaffolds
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We synthesized a new series of PBD-hybrid derivatives having tethered triazoles and investigated for their cytotoxicity. The studies indicated that cis-olefin compounds induce higher cytotoxicity with increase in the G1 cell cycle phase compared with the trans-compounds. Quantitative RT-PCR assay indicated that compounds (16a-d) induced G1 phase arrest through down-regulation of cyclin D1 and up-regulation of p21, p27, and p53 mRNA expressions. Compounds 16a-d induced A375 early apoptosis as detected by flow cytometry after double-staining with annexin V and propidium iodide. Moreover, the Western blot analysis showed that A375 treated by compounds (16a-d) resulted in decreased levels of Bcl-2 and Bcl-xL, increased levels of Bax and Bad, and caspase/PARP degradation to identify apoptotic cells.
- Chen, Chung-Yu,Lee, Pei-Hua,Lin, Yong-Yong,Yu, Wen-Ting,Hu, Wan-Ping,Hsu, Chia-Chen,Lin, Ying-Ting,Chang, Long-Sen,Hsiao, Cheng-Tien,Wang, Jeh-Jeng,Chung, Mei-Ing
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- 4-Aryl- NH -1,2,3-Triazoles via Multicomponent Reaction of Aldehydes, Nitroalkanes, and Sodium Azide
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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
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- The one-pot synthesis of 4-aryl-1H-1,2,3-triazoles without azides and metal catalization
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In this study, a new methodology for the one-pot synthesis of 4-aryl-1H-1,2,3-triazoles from arylglyoxaldoxime semicarbazone is presented. 4-Aryl-1,2,3-triazoles were obtained in moderate to good yields via sodium dithionite and O2, which are all efficient, safe and inexpensive reagents. This reaction is more suitable for large-scale syntheses than those using hydrazoic acid, sodium azide, or organic azides.
- He, Yun,Sun, Erxiao,Zhao, Yi,Hai, Li,Wu, Yong
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- Developments in Pd catalysis: Synthesis of 1H-1,2,3-triazoles from sodium azide and alkenyl bromides
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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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- 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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- Effect of sulfamic acid on 1,3-dipolar cycloaddition reaction: Mechanistic studies and synthesis of 4-Aryl-nh-1,2,3-Triazoles from nitroolefins
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A facile and new metal-free 1,3-dipolar cycloaddition reaction for the synthesis of 4-Aryl NH 1,2,3-Triazoles from nitroolefins and NaN3 employing NH2SO3H has been developed. Sulfamic acid proved to be an efficient additive in this transformation by inhibiting the formation of triaryl benzene. Mechanistic aspects and key intermediates associated with this transformation have also been characterized by online monitoring of the reaction using electrospray ionization tandem mass spectrometry method (ESI-MS/MS). The protocol emphasizes broad substrate scope for many functionalities, simple reaction conditions such as stability to open air, less reaction time, easy work-up, eco-friendly and with good to excellent yields.
- Sharma, Pankaj,Kumar, A. Niggula P.,Senwar, Kishna R.,Forero-Doria, Oscar,Nachtigall, Fabiane M.,Santos, Leonardo S.,Shankaraiah
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- Silver-catalyzed three-component reaction: synthesis of N 2-substituted 1,2,3-triazoles via direct benzylic amination
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A novel Ag(I)-catalyzed benzylic amination reaction with in situ generation of NH-1,2,3-triazoles for N2-substituted 1,2,3-triazole scaffolds is described. This protocol is achieved with easily accessible substrate, broad functional group, good regioselectivity, thus providing the efficient and practical method to diverse N2-substituted 1,2,3-triazole rings with moderate to good yields.
- Liu, Zhenhua,Hao, Wenjing,Gao, Wen,Zhu, Guangyu,Li, Xiang,Tong, Lili,Tang, Bo
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- Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety
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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.
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- Cycloaddition of: N -sulfonyl and N -sulfamoyl azides with alkynes in aqueous media for the selective synthesis of 1,2,3-triazoles
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The cycloaddition of N-sulfonyl and N-sulfamoyl azides with terminal alkynes generally produces amide derivatives via ketenimine intermediates. We herein delineate a Cu(i) catalyzed method using a prolinamide ligand that selectively generates N-sulfonyl a
- Prasanth, Thumpati,Chakraborti, Gargi,Mandal, Tirtha,Ravichandiran, Velayutham,Dash, Jyotirmayee
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p. 911 - 915
(2022/02/02)
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- Base-Induced Highly Regioselective Synthesis of N2-Substituted 1,2,3-Triazoles under Mild Conditions in Air
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We developed a highly regioselective base-induced synthesis of N2-substituted 1,2,3-triazoles from N-sulfonyl-1,2,3-triazoles and alkyl bromides/alkyl iodides at room temperature. We propose an SN2-like mechanistic pathway to explain the high N2-regioselectivity. The protocol features a broad substrate scope and generates products in good to excellent yields (72–90%).
- Ji, Jian,Guan, Cong,Wei, Qinghua,Chen, Xuwen,Zhao, Yun,Liu, Shunying
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supporting information
p. 132 - 136
(2022/01/04)
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- Access to (Z)-β-Substituted Enamides from N1-H-1,2,3-Triazoles
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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
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p. 6293 - 6298
(2021/08/23)
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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
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p. 7499 - 7505
(2021/10/12)
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- Direct Synthesis of 4-Aryl-1,2,3-triazoles via I2-Promoted Cyclization under Metal- And Azide-Free Conditions
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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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supporting information
p. 13664 - 13672
(2021/10/01)
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- Oxoammonium Salt-Mediated Vicinal Oxyazidation of Alkenes with NaN3: Access to β-Aminooxy Azides
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An approach to the vicinal oxyazidation of alkenes has been achieved under mild and transition metal-free conditions. This method utilizes NaN3 as the azidation agent and 2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate (TEMPO
- Chen, Fei,Tang, Yu-Ting,Li, Xin-Ru,Duan, Yan-Yan,Chen, Chao-Xing,Zheng, Yang
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supporting information
p. 5079 - 5084
(2021/09/18)
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- Palladium-Catalyzed Direct Diarylation of 2-Benzyl-1,2,3-triazole: a Simple Access to 4-Aryl- or 4,5-Diaryl-2-benzyl-1,2,3-triazoles and Phenanthro[9,10-d][1,2,3]triazoles
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The reactivity of 2-benzyl-1,2,3-triazole in palladium-catalyzed direct arylation was studied. The reaction conditions for the selective synthesis of 2-benzyl-4-aryl-1,2,3-triazoles in moderate to high yields using phosphine-free Pd(OAc)2 catalyst and inexpensive KOAc base have been found. Then, from these 4-aryl-1,2,3-triazoles, the palladium-catalyzed C?H bond functionalization of the C5-position allowed the synthesis of the corresponding 4,5-diarylated 2-benzyl-1,2,3-triazoles. This selective 4,5-diarylation of 2-benzyl-1,2,3-triazole was successfully applied for the straightforward building of the π-extended polycyclic heteroaromatic structures phenanthro[9,10-d][1,2,3]triazoles through Pd-catalyzed C4- and C5-intermolecular arylations followed by Pd-catalyzed C?H intramolecular arylation.
- Doucet, Henri,Roisnel, Thierry,Shi, Xinzhe,Soulé, Jean-Fran?ois,Zhang, Jian
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p. 2375 - 2382
(2021/06/28)
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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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- Magnetically separable ZnFe2O4 nanoparticles: A low cost and sustainable catalyst for propargyl amine and NH-triazole synthesis
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The multicomponent reaction (MCR) strategy for the construction of important molecular scaffolds is in trending nowadays and among them, A3-coupling stands in a significant position. Aldehyde, amine and alkynes are coupled in this particular reaction via C-H activation process. Herein, we have reported zinc ferrite nanoparticles as magnetically separable heterogeneous catalyst for A3-coupling reaction with attractive attributes like excellent productivity, selectivity and better reusability. Moreover, the catalyst can also be effectively applied for the synthesis of various NH-triazoles with quantitative yields of the products. A plausible mechanism has been proposed for the synthesis of NH-triazoles followed by validation with computational study.
- Bordoloi, Ankur,Chetia, Swadhin,Garg, Anirban,Guha, Ankur Kanti,Hazarika, Roktopol,Kalita, Amlan Jyoti,Kulshrestha, Akshay,Kumar, Arvind,Phukan, Parmita,Sarma, Diganta
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- A green metal-free "one-pot" microwave assisted synthesis of 1,4-dihydrochromene triazoles
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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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- Sulfonic acid-functionalized magnetic carbon nitride as highly efficient ionic composite for sustainable assembly of 1,2,3-triazoles
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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
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p. 2057 - 2064
(2021/02/01)
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- A Scalable Metal-, Azide-, and Halogen-Free Method for the Preparation of Triazoles
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A scalable metal-, azide-, and halogen-free method for the synthesis of substituted 1,2,3-triazoles has been developed. The reaction proceeds through a 3-component coupling of α-ketoacetals, tosyl hydrazide, and a primary amine. The reaction shows outstanding functional-group tolerance with respect to both the α-ketoacetal and amine coupling partners, providing access to 4-, 1,4-, 1,5-, and 1,4,5-substituted triazoles in excellent yield. This robust method results in densely functionalised 1,2,3-triazoles that remain challenging to prepare by azide–alkyne cycloaddition (AAC, CuAAC, RuAAC) methods and can be scaled in either batch or flow reactors. Methods for the chemoselective reaction of either aliphatic amines or anilines are also described, revealing some of the potential of this novel and highly versatile transformation.
- Clark, Peter R.,Hayes, Jerome F.,Tomkinson, Nicholas C. O.,Williams, Glynn D.
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supporting information
p. 6740 - 6744
(2020/03/23)
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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
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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
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supporting information
p. 2233 - 2236
(2020/04/16)
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- Bifunctional 1, 2, 3-triazole derivative intermediate, preparation method and application thereof
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The invention provides a bifunctional 1, 2, 3-triazole derivative intermediate, a preparation method and application thereof. The chemical structure of the bifunctional 1, 2, 3-triazole derivative intermediate is shown as formula I in the specification, wherein R is selected from aryl, electron-donating or electron-withdrawing substituted aryl, electron-donating or electron-withdrawing heteroaryl,alkyl of C1-C6 straight-chain or branched-chain, and alkoxy of C1-C2 straight-chain or branched-chain; R1 is selected from alkyl of C1-C6 straight-chain or branched-chain, aryl, substituted aryl, heterocyclyl, substituted heterocyclyl, aromatic hetero group and substituted aromatic hetero group. The preparation method includes: taking terminal alkyne, a 2, 4, 6-tribromophenyl azide and a sodium sulfinate compound as the raw materials, and carrying out heating for reaction under the action of a catalyst and an additive so as to obtain the bifunctional 1, 2, 3-triazole derivative intermediate.The catalyst is a cuprous salt and a palladium-containing compound, and the additive is an alkaline compound.
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Paragraph 0121; 0134-0138
(2020/03/17)
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- An Efficient Mesoporous Cu-Organic Nanorod for Friedl?nder Synthesis of Quinoline and Click Reactions
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Within the green chemistry context, heterogeneous catalysis for the synthesis of N-heterocycles from renewable resources using non-precious metals has garnered great interest in terms of economic and environmental perspectives. Herein, we present a triazine functional hierarchical mesoporous organic polymer (HMOP) with nanorod morphology together with large BET surface area ~1218 m2 g?1, huge pore volumeγτ“;6 mL g?1 and dual micro/mesopore architectures. Subsequent Cu-coordination with nitrogen atoms of the HMOP provides a robust catalyst (Cu-HMOP) to accomplish multi-step cascade reactions for preparation of N-heterocycles by different routes. For instance, the Cu-HMOP efficiently catalyzes one-pot sequential multi-step oxidative dehydrogenative coupling of 2-aminobenzyl alcohol with diverse aromatic ketones to afford corresponding quinolines in excellent isolated yields (up to 97 %). Secondly, the present catalyst exhibits good aerobic oxidative dehydrogenation activity of amines to imines. Thirdly, for “click” reaction involving azides-alkynes, the Cu-HMOP produced quantitative yield for 1,4-disubstituted 1,2,3-triazole derivatives at room temperature using water as solvent. Verification of active metal leaching by a hot filtration test as well as reusability of the retrieved Cu-HMOP catalysts shows a consistent activity in the multi-component quinoline synthesis as model reaction.
- Elavarasan, Samaraj,Bhaumik, Asim,Sasidharan, Manickam
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p. 4340 - 4350
(2019/08/12)
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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
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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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- 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
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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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- Metal-Free Cascade [4 + 1] Cyclization Access to 4-Aryl- NH-1,2,3-triazoles from N-Tosylhydrazones and Sodium Azide
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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
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p. 14919 - 14925
(2019/11/11)
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- On Water Cu@g-C3N4 Catalyzed Synthesis of NH-1,2,3-Triazoles via [2+3] Cycloadditions of Nitroolefins/Alkynes and Sodium Azide
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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
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p. 5468 - 5474
(2018/11/23)
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- Synthesis of heterogeneous Ru(ii)-1,2,3-triazole catalyst supported over SBA-15: Application to the hydrogen transfer reaction and unusual highly selective 1,4-disubstituted triazole formation: Via multicomponent click reaction
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In the present study, we demonstrate a simple and efficient method for ligand formation and covalent anchoring to a heterogeneous support via click reaction. The complex tris(triphenylphosphine)ruthenium(ii) dichloride [RuCl2(PPh3)3] anchored over the click modified ligand of SBA-15 forms a new highly efficient heterogeneous SBA-15-Tz-Ru(ii)TPP catalyst. Solid state 13C, 29Si, and 31P CP-MAS NMR spectra provide evidence for the formation of the heterogeneous catalyst. SBA-15-Tz-Ru(ii)TPP catalyst was screened for the multicomponent click cycloaddition reaction in water medium as a green solvent and it exhibited unusual and excellent selectivity for the formation of 1,4-disubstituted triazole product under mild reaction condition. In addition, SBA-15-Tz-Ru(ii)TPP catalyst also catalyzed the hydrogen transfer reaction of various carbonyl compounds with excellent catalytic activity to give the corresponding alcohols. The heterogeneous catalyst can be recycled and reused several times (five) without a loss in reactivity.
- Sharma, Priti,Rathod, Jayant,Singh,Kumar, Pradeep,Sasson, Yoel
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p. 3246 - 3259
(2018/07/13)
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- Investigation of copper-free alkyne/azide 1,3-dipolar cycloadditions using microwave irradiation
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The prevalence of 1,3-dipolar cycloadditions of azides and alkynes within both biology and chemistry highlights the utility of these reactions. However, the use of a copper catalyst can be prohibitive to some applications. Consequently, we have optimized
- Chatkewitz, Lindsay E.,Halonski, John F.,Padilla, Marshall S.,Young, Douglas D.
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supporting information
p. 81 - 84
(2017/12/28)
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- Sulfonation of carbonized xylan-type hemicellulose: A renewable and effective biomass-based biocatalyst for the synthesis of O- and N-heterocycles
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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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supporting information
p. 9140 - 9150
(2018/06/11)
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- Synthesis of tetrazoles, triazoles, and imidazolines catalyzed by magnetic silica spheres grafted acid
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The magnetically separable catalysts are used in the synthesis of N-containing heterocycles, including tetrazoles, triazoles, and imidazolines. The magnetic silica sphere grafted sulfonic acid (MSS-SO3H) is suitable for the synthesis of 1,2,3-triazole via the cycloaddition of nitroalkene with NaN3, whereas the zinc-modified silica sphere catalyst (MSS-SO3Zn) is more suitable for the synthesis of tetrazoles. The MSS-SO3Zn catalyst also works well for the synthesis of 2-substituted imidazoline via the condensation of nitriles with ethylenediamine. Both of the MSS-SO3H and MSS-SO3Zn catalysts can be recovered easily by a magnet, and they can be reused without further tedious activation.
- Jiang, Ruihang,Sun, Hong-Bin,Li, Shuang,Zhan, Kun,Zhou, Junjie,Liu, Lei,Zhang, Kai,Liang, Qionglin,Chen, Zhangpei
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supporting information
p. 2652 - 2662
(2018/11/26)
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- A mineralogically-inspired silver-bismuth hybrid material: An efficient heterogeneous catalyst for the direct synthesis of nitriles from terminal alkynes
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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
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p. 1007 - 1019
(2018/03/13)
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- Copper(I)-Catalyzed Synthesis of 1,4-Disubstituted 1,2,3-Triazoles from Azidoformates and Aryl Terminal Alkynes
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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)
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- Magnetically recoverable copper ferrite catalyzed cascade synthesis of 4-Aryl-1H-1,2,3-triazoles under microwave irradiation
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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)
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- Method of catalytically synthesizing 4-aryl-NH-1,2,3-triazole derivative under microwave radiation
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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
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Paragraph 0010
(2018/03/26)
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- Synthesis of 1,2,3-triazoles in the presence of mixed Mg/Fe oxides and their evaluation as corrosion inhibitors of API 5L X70 steel submerged in HCl
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In this work, the catalytic capacity of a Mg/Fe layered double hydroxide (LDH) and its mixed oxides to perform Huisgen cycloaddition was studied. The catalytic process was performed in the presence of sodium ascorbate, which was determinant for the success of the 1,3-cycloaddition. The obtained triazoles were evaluated as corrosion inhibitors using electrochemical impedance spectroscopy under static conditions, showing an inhibition efficiency higher than 95% at 50 ppm for some of the triazoles studied. According to the Langmuir isotherm, all the compounds synthesized and analysed exhibit a chemisorption process. Finally, the corrosion process when submerging a steel bar in 1 M HCl was studied using SEM-EDS. This experiment showed that the corrosion process decreases considerably in the presence of 50 ppm of the organic inhibitor.
- Espinoza-Vázquez,Rodríguez-Gómez,Vergara-Arenas,Lomas-Romero,Angeles-Beltrán,Negrón-Silva,Morales-Serna
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p. 24736 - 24746
(2017/07/11)
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- Synthesis of N-unsubstituted 1,2,3-triazoles via aerobic oxidative N-dealkylation using copper(II) acetate
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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
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p. 2878 - 2885
(2017/04/26)
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- Multicomponent synthesis of 4-aryl-NH-1,2,3-triazoles in the presence of Al-MCM-41 and sulfated zirconia
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The acid properties of Al-MCM-41 and sulfated zirconia were used to develop a strategy for the synthesis of 4-aryl-NH-1,2,3-triazoles via a multicomponent reaction involving various benzaldehydes, sodium azide and nitromethane. The efficiency of the process is analysed from the perspective of the difference in acids among the catalysts used.
- Vergara-Arenas, Blanca Ivonne,Lomas-Romero, Leticia,ángeles-Beltrán, Deyanira,Negrón-Silva, Guillermo Enrique,Gutiérrez-Carrillo, Atilano,Lara, Víctor Hugo,Morales-Serna, José Antonio
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supporting information
p. 2690 - 2694
(2017/06/23)
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- Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates
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Cyanophosphates (CPs) can be easily prepared from either ketones or aldehydes, and their reaction with NaN3-Et3N·HCl results in the formation of azidotetrazoles. Under microwave irradiation, successive fragmentation of the azidotetrazoles generates alkylidene carbenes that undergo [1,2]-rearrangement and are transformed into homologous alkynes. Treatment of ketone-derived CPs with TMSN3 and Bu2SnO as catalyst in toluene at reflux directly yields the corresponding internal alkynes, whereas the reaction of aldehyde-derived CPs with NaN3-Et3N·HCl in THF at reflux or TMSN3-Bu2SnO (cat.) in toluene at reflux provides homologous terminal alkynes in good yields. These reactions take place under neutral conditions and can be successfully extended to obtain alkynes that are not usually accessible from the corresponding carbonyl compounds by the Ohira-Bestmann or Shioiri procedures, which require basic conditions.
- Yoneyama, Hiroki,Numata, Masahiro,Uemura, Kenji,Usami, Yoshihide,Harusawa, Shinya
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p. 5538 - 5556
(2017/06/07)
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- One-Pot Synthesis of 4-Aryl-NH-1,2,3-Triazoles through Three-Component Reaction of Aldehydes, Nitroalkanes and NaN3
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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
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p. 1808 - 1812
(2017/09/06)
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- Intensified synthesis of [3,4-d]triazole-fused chromenes, coumarins, and quinolones
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Abstract: Efficient and metal-free synthesis of [3,4-d]triazole-fused chromenes, coumarins, and quinolones has been achieved in an intensified regime using microwave heating. The smooth 1,3-dipolar cycloaddition reaction of heterocyclic nitroalkenes with
- Schwendt, Georg,Glasnov, Toma
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- DABCO-mediated aza-Michael addition of 4-aryl-1H-1,2,3-triazoles to cycloalkenones. Regioselective synthesis of disubstituted 1,2,3-triazoles
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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
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supporting information
p. 298 - 301
(2017/01/03)
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- N 1-Selective alkenylation of 1-sulfonyl-1,2,3-triazoles with alkynes via gold catalysis
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A N1-selective alkenylation of 1-sulfonyl-1,2,3-triazoles with alkynes via gold catalysis is reported. N1-Vinyl substituted 1,2,3-triazoles were selectively prepared in up to 92% yield through the sulfonyl group of 1,2,3-triazole der
- Sun, Chenyang,Yuan, Xiao,Li, Yan,Li, Xiaoxiao,Zhao, Zhigang
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p. 2721 - 2724
(2017/04/04)
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- Magnetically Recoverable Cu0/Fe3O4-Catalysed One-Pot Tandem Synthesis of Sulfur-Containing Triazoles from Alkynes and Azide: DMSO Acts as an Alkylating Agent
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An efficient one-pot tandem nano Cu0/Fe3O4-catalysed synthesis of sulfur-containing triazoles from alkynes and azide has been developed. In this newly developed method, the readily available TMS-azide and dimethyl sulfoxide act as nitrogen and sulfur sources, respectively. The catalyst was magnetically recovered and reused six times without any significant loss of activity.
- Phanindrudu, Mandalaparthi,Tiwari, Dipak Kumar,Aravilli, Vinod Kumar,Bhardwaj, Kishor Chandra,Sabapathi, Gokulnath,Likhar, Pravin R.,Tiwari, Dharmendra Kumar
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supporting information
p. 4629 - 4634
(2016/09/28)
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- A single-step acid catalyzed reaction for rapid assembly of: NH -1,2,3-triazoles
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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
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supporting information
p. 9236 - 9239
(2016/07/25)
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- Synthesis method of NH-1,2,3-triazole compound
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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.
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Paragraph 0012; 0013; 0014; 0015; 0016
(2017/07/20)
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- Method for preparing 4-aryl-NH-1,2,3-triazole by aid of aldehyde and sodium bisulfite adduct
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The invention relates to a method for preparing 4-aryl-NH-1,2,3-triazole by the aid of aldehyde and sodium bisulfite adduct. The method is characterized by comprising steps as follows: the aldehyde and sodium bisulfite adduct, a nitrocompound, sodium azide, a solvent and an additive react at the temperature of 60-150 DEG C for 1-10 h with a one-pot method, after the reaction ends, aftertreament is performed, and 4-aryl-NH-1,2,3-triazole can be prepared. The cheap and easy-to-obtain aldehyde and sodium bisulfite adduct, nitrocompound and sodium azide are taken as raw materials, and 4-aryl-NH-1,2,3-triazole compounds can be conveniently prepared from the three components. Compared with existing methods, the method has the advantages that the raw materials are low in cost and simple and easy to obtain, the operation is convenient, and the reaction efficiency is high.
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Paragraph 0012
(2017/01/02)
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- A 'photorelease, catch and photorelease' strategy for bioconjugation utilizing a p-hydroxyphenacyl group
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A bioorthogonal 'catch and photorelease' strategy, which combines alkyne-azide cycloaddition between p-hydroxyphenacyl azide and alkyne derivatives to form a 1,2,3-triazole adduct and subsequent photochemical release of the triazole moiety via a photo-Favorskii rearrangement, is introduced. The first step can also involve photorelease of a strained alkyne and its Cu-free click reaction with azide.
- Madea,Slanina,Klán
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supporting information
p. 12901 - 12904
(2016/11/06)
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