Click chemistry as a versatile reaction for construction and modification of metal-organic frameworks

Li, Pei‐Zhou; Wang, Xiaojun; Zhao, Yanli

doi:10.1016/j.ccr.2018.11.006

Cited by 94 publications

(56 citation statements)

References 255 publications

(300 reference statements)

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“…[9] In this respect, various nitrogen-richM OFs containing triazolate-and tetrazolate-functionalized ligands have been synthesized, [9,10] but the high affinity of these ligands towards metal ions limits the number of open donors ites responsible for CO 2 enhancement duringt he adsorptionp rocess. There are severale xamples of triazole-functionalizedM OFs, [11] but only af ew utilizet etratopic triazole-functionalizedc arboxylates as the organic linkers,i n whicha ll donor sites are availablef or interaction with the CO 2 molecules. It is also envisaged that the accessibility of the functional sites is much more important than the electronic effects,a nd any hindrance to the functional site will limit its effectonimprovingC O 2 uptake capacity and selectivity.…”

Section: Introductionmentioning

confidence: 99%

A Highly Stable Triazole‐Functionalized Metal–Organic Framework Integrated with Exposed Metal Sites for Selective CO₂ Capture and Conversion

Gupta

Mandal

2020

Chemistry A European J

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A new triazole‐functionalized tetracarboxylic acid ligand (H4L) has been synthesized and utilized for the fabrication of a 3D ZnII organic framework with a Zn4(−COO)6 cluster as the secondary building unit. The framework exhibits very good thermal stability and consists of dual functionalities of exposed Lewis acidic metal sites and accessible nitrogen‐donor Lewis basic sites. The Lewis basic nitrogen sites in the framework serve as CO2 binding sites for highly selective CO2 capture and the presence of exposed Lewis acidic metal sites in the framework make it an efficient heterogeneous catalyst for the chemical fixation of CO2 into value‐added cyclic carbonates under ambient conditions.

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Section: Introductionmentioning

confidence: 99%

A Highly Stable Triazole‐Functionalized Metal–Organic Framework Integrated with Exposed Metal Sites for Selective CO₂ Capture and Conversion

Gupta

Mandal

2020

Chemistry A European J

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“…The CuAAC of organic azides and terminal alkynes is considered to be a versatile and promising approach to prepare new bioactive compounds, pharmaceutical lead compounds, bio-probes, soft materials among others [45][46][47][48][49][50].…”

Section: Cuaac Of Azidoethyl-nitroindazoles With Terminal Alkynesmentioning

confidence: 99%

A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions

et al. 2019

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The alkylation of a series of nitroindazole derivatives with 1,2-dibromoethane afforded the corresponding N-(2-bromoethyl)and N-vinyl-nitro-1H-indazoles. The Cu(I)-catalysed azide-alkyne 1,3-dipolar cycloaddition was selected to substitute the nitroindazole core with 1,4-disubstituted triazole units after converting one of the N-(2-bromoethyl)nitroindazoles into the corresponding azide. The reactivity in 1,3-dipolar cycloaddition reactions with nitrile imines generated in situ from ethyl hydrazono-α-bromoglyoxylates was studied with nitroindazoles bearing a vinyl unit. The corresponding nitroindazole-pyrazoline derivatives were obtained in good to excellent yields.Molecules 2020, 25, 126 2 of 18 antipyretic, antioxidant, antiparasitic, antimicrobial, antitumoral and anti-inflammatory activities, among others [5][6][7][21][22][23].Indazoles are another important group of N-heterocycles with significant biological activities as nitric oxide synthase (NOS) inhibitors, kinase inhibitors, anti-inflammatory, anticancer, antimicrobial, antifungal, antimalarial, and antileishmanial agents, among others.Some anticancer and anti-inflammatory drugs based in indazole scaffolds are commercially available [24][25][26][27][28][29][30]. Besides the biological properties presented by indazole derivatives, this family of N-heterocycles also showed potential to be used in other fields as corrosion inhibitors, components for OLEDs and battery applications, and as copolymerizing molecules for new materials [31][32][33][34].Following our interest on developing synthetic approaches to functionalize the indazole core [35,36], we decided to follow the 1,3-dipolar cycloaddition methodology to substitute nitroindazoles with triazole or pyrazoline moieties, aiming in such way to obtain new compounds with improved biological features for different applications. In the strategy envisaged it was considered that the alkylation of indazole with 1,2-dibromoethane using liquid-liquid phase transfer catalysis, could afford not only the N-1and N-2-bromoethylindazoles, but also the corresponding N-1and N-2-vinylindazoles [37]. The annular tautomerisation of two nitrogen atoms (N-1, N-2) present in the indazole ring, has been explored in synthetic and theoretical studies concerning the substitution of N-H-indazole [38]. More recently, it was reported by our group that the reactivity of N-1 and N-2 alkylated indazole isomers is strongly dependent on the reaction conditions, namely, solvent proticity and pH, as well as, electronic and steric effects [39,40].Herein it is described the synthesis of a series of N-bromoethyl-nitroindazoles and N-vinyl-nitroindazoles reacting the corresponding nitroindazoles with 1,2-dibromoethane. A detailed analysis of the reaction conditions allowed to develop a simple, fast and inexpensive protocol to obtain both the vinyl and the bromoethyl derivatives in just one step in reasonable amounts. One of the bromoethyl derivatives was used to afford the corresponding azide, and its reactivity in CuAAC reactions with different...

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“…Fully substituted 1,2,3-triazoles play a signicant role in chemical, biological, and pharmaceutical elds, and are widely applied in chemical medicine and materials science. [1][2][3] The importance of 1,2,3-triazoles has inspired chemists to develop more and more economically and effectively synthetic methods. [4][5][6][7] The synthesis among the substituted 1,2,3-triazoles can be traced back to 1960s, when Huisgen reported a simple and widely useful approach to synthesize a mixture of 1,4-and 1,5-disubstituted 1,2,3-triazole mixture via the 1,3-dipolar cycloaddition reaction of azides and alkynes.…”

Section: Introductionmentioning

confidence: 99%

DFT and AFIR study on the copper(i)-catalyzed mechanism of 5-enamine-trisubstituted-1,2,3-triazole synthesis via C–N cross-coupling and the origin of ring-opening of 2H-azirines

Zhou

Song

et al. 2021

RSC Adv.

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Click chemistry as a versatile reaction for construction and modification of metal-organic frameworks

Cited by 94 publications

References 255 publications

A Highly Stable Triazole‐Functionalized Metal–Organic Framework Integrated with Exposed Metal Sites for Selective CO₂ Capture and Conversion

A Highly Stable Triazole‐Functionalized Metal–Organic Framework Integrated with Exposed Metal Sites for Selective CO₂ Capture and Conversion

A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions

DFT and AFIR study on the copper(i)-catalyzed mechanism of 5-enamine-trisubstituted-1,2,3-triazole synthesis via C–N cross-coupling and the origin of ring-opening of 2H-azirines

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Click chemistry as a versatile reaction for construction and modification of metal-organic frameworks

Cited by 94 publications

References 255 publications

A Highly Stable Triazole‐Functionalized Metal–Organic Framework Integrated with Exposed Metal Sites for Selective CO2 Capture and Conversion

A Highly Stable Triazole‐Functionalized Metal–Organic Framework Integrated with Exposed Metal Sites for Selective CO2 Capture and Conversion

A Suitable Functionalization of Nitroindazoles with Triazolyl and Pyrazolyl Moieties via Cycloaddition Reactions

DFT and AFIR study on the copper(i)-catalyzed mechanism of 5-enamine-trisubstituted-1,2,3-triazole synthesis via C–N cross-coupling and the origin of ring-opening of 2H-azirines

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A Highly Stable Triazole‐Functionalized Metal–Organic Framework Integrated with Exposed Metal Sites for Selective CO₂ Capture and Conversion

A Highly Stable Triazole‐Functionalized Metal–Organic Framework Integrated with Exposed Metal Sites for Selective CO₂ Capture and Conversion