16219-51-5Relevant articles and documents
Synthesis of Novel 1,2,3-Triazole-Dihydropyrimidinone Hybrids Using Multicomponent 1,3-Dipolar Cycloaddition (Click)-Biginelli Reactions: Anticancer Activity
Burke, Anthony J.,Carreiro, Elisabete P.,Sena, Ana M.,Padrón, José M.,Puerta, Adrián
, p. 615 - 621 (2020)
In this work, 21 novel (1,4-disubstituted 1,2,3-triazole)-dihydropyrimidinone (1,2,3-trzl-DHPM) type hybrids were synthesized and characterized. These were divided into two types: hybrids A (5 in total) containing the dihydropyrimidinone heterocyclic ring decorated with a 1,4-disubstituted 1,2,3-triazole in the C-5 position [these compounds were accessed by a multicomponent copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) (or click)-Biginelli reactions with satisfactory yields (39-57%)] and hybrids B (16 in total) containing two 1,2,3-triazole units in the C-5 and C-6 methyl position of the DHPM. Hybrids B were synthesized via functionalization of the C-6 methyl group of hybrids A, a multistep sequence of reactions was used that included bromination, azidation, and a CuAAC. Hybrids B were obtained in very good to excellent yields (up to 99%). Some hybrids A and B were evaluated for their antiproliferative activity against different cancer cell lines that included A549 and SW1573 (non-small-cell lung), HBL-100 and T-47D (breast), HeLa (cervix) and WiDr (colon). Three of these hybrids were potent cell proliferation inhibitors of non-small-cell lung cancer, cervix cancer, breast cancer, and colon cancer.
Tandem catalysis of an aldol-'click' reaction system within a molecular hydrogel
Araújo, Marco,Capdevila, Iván Mu?oz,Díaz-Oltra, Santiago,Escuder, Beatriu
, (2016)
A heterogeneous supramolecular catalytic system for multicomponent aldol-'click' reactions is reported. The copper(I) metallohydrogel functionalized with a phenyltriazole fragment was able to catalyze the multicomponent reaction between phenylacetylene, p
Synthesis of aliphatic α-ketoamides from α-substituted methyl ketones: Via a Cu-catalyzed aerobic oxidative amidation
Cha, Hyojin,Chai, Jin Young,Chi, Dae Yoon,Kim, Hyeong Baik
supporting information, p. 4320 - 4326 (2021/05/31)
α-Ketoamides are an important key functional group and have been used as versatile and valuable intermediates and synthons in a variety of functional group transformations. Synthetic methods for making aryl α-ketoamides as drug candidates have been greatly improved through metal-catalyzed aerobic oxidative amidations. However, the preparation of alkyl α-ketoamides through metal-catalyzed aerobic oxidative amidations has not been reported because generating α-ketoamides from aliphatic ketones with two α-carbons theoretically provides two distinct α-ketoamides. Our strategy is to activate the α-carbon by introducing an N-substituent at one of the two α-positions. The key to this strategy is how heterocyclic compounds such as triazoles and imidazoles affect the selectivity of the synthesis of the alkyl α-ketoamides. From this basic concept, and by optimizing the reaction and elucidating the mechanism of the synthesis of aryl α-ketoamides via a copper-catalyzed aerobic oxidative amidation, we prepared fourteen aliphatic α-ketoamides in high yields (48-84%). This journal is
Triazole-bearing calixpyrroles: Strong halide binding affinities through multiple N-H and C-H hydrogen bonds
Kim, Hyeongcheol,Hong, Kyeong-Im,Lee, Jeong Heon,Kang, Philjae,Choi, Moon-Gun,Jang, Woo-Dong
supporting information, p. 10863 - 10865 (2018/10/02)
Triazole-bearing calixpyrroles (TCPs) were synthesized as artificial anion binding receptors. The additional C-H?X hydrogen bonding interaction induced strong binding affinity towards halide ions. Using this strong binding affinity, Cl- was successfully extracted from the aqueous to organic phase.
[bmim]BF4/[Cu(Im12)2]CuCl2 as a novel catalytic reaction medium for click cyclization
Keshavarz, Mosadegh,Karami, Bahador,Ahmady, Amanollah Zarei,Ghaedi, Abdolmohammad,Vafaei, Hakimeh
, p. 570 - 576 (2014/06/09)
Herein, a new application of an ionic liquid containing copper (I), ([Cu(Im12)2]CuCl2), is introduced. This ionic liquid was used as an efficient catalyst for the click cyclization between organic azides and terminal alkyn
Polymer-supported azide and copper(I): Green reusable reagent and catalyst for click cyclization
Albadi, Jalal,Keshavarz, Mosadegh
, p. 2019 - 2030 (2013/06/05)
In this work, polymer-supported copper(I) iodide catalyst and macroporous polymer-supported azide reagent were used to simplify the synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from α-bromo ketones/amides/esters following green chemistry principles.
Ionic liquid containing copper(I): A new, green, homogeneous, and reusable catalyst for click cyclization
Ahmady, Amanollah Zarei,Heidarizadeh, Fariba,Keshavarz, Mosadegh
, p. 2100 - 2109 (2013/06/05)
An ionic liquid containing copper(I) is introduced as a new, green, homogeneous, and reusable catalyst for click synthesis of 1,4-disubstituted-1H- 1,2,3-triazoles from α-azido ketones and terminal alkynes in various solvents, especially in [bmim]BF4
Copper iodide nanoparticles on poly(4-vinyl pyridine): A new and efficient catalyst for multicomponent click synthesis of 1,4-disubstituted-1,2,3-triazoles in water
Albadi, Jalal,Keshavarz, Mosadegh,Shirini, Farhad,Vafaie-Nezhad, Masoumeh
, p. 17 - 20 (2012/10/29)
Polymer supported nanoparticles of copper(I) iodide is reported as a new, efficient and recyclable catalyst for the regioselective multicomponent synthesis of 1,4-disubstituted-1H-1,2,3-triazoles from α-halo ketones, sodium azide and terminal alkynes in w
A facile and regioselective synthesis of 1,4-disubstituted 1,2,3-triazoles using click chemistry
Kumar, Dalip,Reddy, V. Buchi,Varma, Rajender S.
experimental part, p. 2065 - 2068 (2009/09/05)
The reaction of α-tosyloxy ketones, sodium azide, and terminal alkynes in presence of copper(I) in aqueous polyethylene glycol afforded regioselectively 1,4-disubstituted 1,2,3-triazoles in good yield at ambient temperature. The one-pot exclusive formatio
