57134-58-4Relevant academic research and scientific papers
The 2-(4-Phenyl-1H-1,2,3-triazol-1-yl)ethanol-Based Phosphinite Ligand Ph2POCH2CH2[1,2,3-N3C(Ph)C(H)] – Synthesis, Transition-Metal Complexes, and Structural Studies
Choubey, Bimba,Prasad, Pandey Sameer,Mague, Joel T.,Balakrishna, Maravanji S.
, p. 1707 - 1714 (2018)
The synthesis and coordination complexes of the new 1,2,3-triazole phosphinite Ph2POCH2CH2[1,2,3-N3C(Ph)C(H)] (2) are described. Compound 2 reacts with H2O2, S8, and Se8 to afford the chalcogenides Ph2P(=E)OCH2CH2[1,2,3-N3C(Ph)C(H)] [E = O (3), S (4), and Se (5)]. The reaction of 2 with [Ru(η6-cymene)Cl2] yielded [Ru(η6-cymene)Cl2(Ph2POCH2CH2{1,2,3-N3C(Ph)C(H)})] (6), which produced [Ru(η6-cymene)(Ph2POCH2CH2{1,2,3-N3C(Ph)C(H)})]2[OTf]2 (7) on further treatment with silver triflate (AgOTf); in 7, 2 acts as a bidentate (P,N) ligand. The reaction of 2 with [CpRuCl(PPh3)2] (Cp = cyclopentadienyl) in 1:1 and 1:2 molar ratios afforded the mono- and disubstituted complexes [CpRuCl(PPh3)(Ph2POCH2CH2{1,2,3-N3C(Ph)C(H)})] (8) and [CpRuCl(Ph2P-OCH2CH2{1,2,3-N3C(Ph)C(H)})2] (9), respectively. Complex 9 reacted with silver triflate to yield the cationic complex [CpRu(Ph2POCH2CH2{1,2,3-N3C(Ph)C(H)})(Ph2POCH2CH2{1,2,3-N3C(Ph)C(H)})][OTf] (10), in which one of the phosphinite ligands shows P,N-chelation. The reactions of 2 with [M(COD)Cl2] (M = Pd, Pt; COD = 1,5-cyclooctadiene) in 2:1 ratios yielded cis-[MCl2(Ph2POCH2CH2{1,2,3-N3C(Ph)C(H)})2] [M = Pd (11) and Pt (12)]. The similar reaction of 2 with [PdCl(η3-C3H5)]2 in a 2:1 ratio afforded [PdCl(η3-C3H5)(Ph2POCH2CH2{1,2,3-N3C(Ph)C(H)})] (13). The reaction of 2 with [AuCl(SMe2)] in a 1:1 ratio yielded [Au(Cl)(Ph2POCH2CH2{1,2,3-N3C(Ph)C(H)})2] (14). The molecular structures of 6, 7, 9, 11, and 12 were determined by single-crystal X-ray studies.
Base-Free Copper-Catalyzed Azide-Alkyne Click Cycloadditions (CuAAc) in Natural Deep Eutectic Solvents as Green and Catalytic Reaction Media**
Giofrè, Salvatore Vincenzo,Tiecco, Matteo,Ferlazzo, Angelo,Romeo, Roberto,Ciancaleoni, Gianluca,Germani, Raimondo,Iannazzo, Daniela
, p. 4777 - 4789 (2021/08/30)
The click cycloaddition of azides to alkynes affording 1,2,3-triazoles is a widely used and effective chemical transformation, applied to obtain relevant products in medicine, biology, and materials science. In this work, a set of natural deep eutectic so
Visible-Light-Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron-Transfer Strategy
Wu, Zheng-Guang,Liao, Xiang-Ji,Yuan, Li,Wang, Yi,Zheng, You-Xuan,Zuo, Jing-Lin,Pan, Yi
supporting information, p. 5694 - 5700 (2020/04/24)
Click chemistry focuses on the development of highly selective reactions using simple precursors for the exquisite synthesis of molecules. Undisputedly, the CuI-catalyzed azide–alkyne cycloaddition (CuAAC) is one of the most valuable examples of click chemistry, but it suffers from some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate a novel strategy for the azide–alkyne cycloaddition reaction that involves a photoredox electron-transfer radical mechanism instead of the traditional metal-catalyzed coordination process. This newly developed photocatalyzed azide–alkyne cycloaddition reaction can be performed under mild conditions at room temperature in the presence of air and visible light and shows good functional group tolerance, excellent atom economy, high yields of up to 99 %, and absolute regioselectivity, affording a variety of 1,4-disubstituted 1,2,3-triazole derivatives, including bioactive molecules and pharmaceuticals. The use of a recyclable photocatalyst, solar energy, and water as solvent makes this photocatalytic system sustainable and environmentally friendly. Moreover, the azide–alkyne cycloaddition reaction could be photocatalyzed in the presence of a metal-free catalyst with excellent regioselectivity, which represents an important development for click chemistry and should find versatile applications in organic synthesis, chemical biology, and materials science.
Copper-catalyzed decarboxylation/cycloaddition cascade of alkynyl carboxylic acids with azide
Shang, Jia-Qi,Fu, Hong,Li, Yi,Yang, Tao,Gao, Chuanzhu,Li, Ya-Min
, p. 253 - 259 (2018/12/11)
A copper-catalyzed decarboxylation/cycloaddition cascade of alkynyl carboxylic acids with azide has been developed. This reaction exhibits good functional group tolerance and wide substrate scope, provides an efficient way to construct 1,4-disubstituted 1
Ultrasound Assisted High-Throughput Synthesis of 1,2,3-Triazoles Libraries: A New Strategy for “Click” Copper-Catalyzed Azide-Alkyne Cycloaddition Using Copper(I/II) as a Catalyst
El-bendary, Mohamed M.,Saleh, Tamer S.,Al-Bogami, Abdullah S.
, p. 3797 - 3810 (2018/10/15)
Abstract: A series of 1,4-disubstituted 1,2,3-triazoles were prepared by a parallel synthesis protocol utilizing the 3D-supramolecular coordination polymer (SCP) {[CuI(CN)(phen)2·CuII(CN)2(phen)]·5H2O
Direct access to stabilized CuI using cuttlebone as a natural-reducing support for efficient CuAAC click reactions in water
Ghodsinia, Sara S. E.,Akhlaghinia, Batool,Jahanshahi, Roya
, p. 63613 - 63623 (2016/07/19)
Cuttlebone@CuCl2 has efficiently catalyzed the one-pot azidonation of organic bromides, followed by a regioselective azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction to produce the corresponding 1,4-disubstituted 1,2,3-triazole derivativ
Copper(I) Confined in Interlayer Space of Montmorillonite: A Highly Efficient and Recyclable Catalyst for Click Reaction
Mekhzoum, Mohammed El Mehdi,Benzeid, Hanane,Qaiss, Abou El Kacem,Essassi, El Mokhtar,Bouhfid, Rachid
, p. 136 - 143 (2016/03/12)
CuI-exchanged solid based on montmorillonite material was investigated as catalyst in organic synthesis. The catalytic potential of this material was evaluated in the Huisgen [3 + 2]cycloaddition. This catalytic system has been examined and pro
Polystyrene resin supported palladium(0) (Pd@PR) nanocomposite mediated regioselective synthesis of 4-aryl-1-alkyl/(2-haloalkyl)-1H-1,2,3-triazoles and their N-vinyl triazole derivatives from terminal alkynes
Shil, Arun K.,Kumar, Sandeep,Sharma, Saurabh,Chaudhary, Abha,Das, Pralay
, p. 11506 - 11514 (2015/02/19)
An efficient general methodology has been developed for sequential one-pot synthesis of 4-aryl-1-alkyl-1H-1,2,3-triazoles influenced by polystyrene resin supported palladium(0) (Pd@PR) nanocomposite as a heterogeneous catalyst. The present work particularly emphasizes the synthesis of 4-aryl-1-(2-haloalkyl)-1H-1,2,3-triazoles through the selective mono-azidation of 1,2-dihaloethane and subsequent Pd@PR mediated 1,3-dipolar cycloaddition with terminal aryl alkynes. Potassium carbonate promoted dehydrohalogenation of synthesized 4-aryl-1-(2-haloalkyl)-1H-1,2,3-triazoles gave the corresponding N-vinyl derivatives (often used as building blocks for polymers) which are further utilized in the synthesis of 4-aryl-1-(2-arylalkenyl)-1H-1,2,3-triazoles following a Pd@PR catalyzed Heck coupling approach. Furthermore, microwave assisted one pot dehydrochlorination and Heck strategy was adopted to afford 4-phenyl-1-styryl-1H-1,2,3-triazole under Pd@PR catalyzed conditions using iodobenzene as a phenylating agent.
SULFONATE COMPOUNDS HAVING ORGANIC SALTS, ORGANO FLUORO COMPOUNDS COMPOUND HAVING ORGANIC SALTS USING THE SAME AND METHOD FOR MANUFACTURING THE SAME
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Paragraph 0095-0097, (2016/11/17)
The present invention relates to a sulfonate compound having organic salts, an organic fluoro compound having organic salts produced by using the same, and a method for producing the same. More particularly, the present invention relates to: an organic fluoro compound having organic salts which is used to manufacture an 18F-labeled or 19F-labeled radiopharmaceutical product for positron emission tomography (PET); an organic fluoro compound having organic salts produced by using the same; and a method for producing the same. According to the present invention, the sulfonate compound having organic salts and the organic fluoro compound are easily dissolved in a polar solvent such as an aqueous solution due to organic salts in the compound and thus enables conjugation reaction with a polar compound which is, for example, a biocompound such as peptides, protein, glucose, and nucleotides to be performed in an easy manner.(AA) Lyophilic fluorination reaction(BB) Conversion ratio(CC) Example (compound 1b)(DD) Example (compound 1c)(EE) Example (compound 1d)(FF) Comparative example (compound 10)(GG) Time (minute)COPYRIGHT KIPO 2016
Synthesis and biological evaluation of 3-hydroxymethyl-5-(1H-1,2,3-triazol) isoxazolidines
Romeo, Roberto,Giofrè, Salvatore V.,Carnovale, Caterina,Campisi, Agata,Parenti, Rosalba,Bandini, Lorenzo,Chiacchio, Maria A.
, p. 7929 - 7937 (2014/01/06)
A synthetic approach towards a series of 3-hydroxymethyl-5-(1H-1,2,3- triazol)isoxazolidines has been reported, according to a procedure based on the cycloaddition reaction, under microwave irradiation, of a nitrone with 1-vinyl triazoles, prepared by a click reaction of azides with alkynes. Biological tests show that the synthesized compounds are able to inhibit proliferation of follicular and anaplastic human thyroid cancer cell lines, with IC50 values ranging from 3.87 to 8.76 μM. The obtained compounds induce caspase-3 activation and DNA fragmentation prevalently in follicular human thyroid cancer cell lines.
