Advances in click chemistry for silica-based material construction

RSC Advances ◽  
2016 ◽  
Vol 6 (26) ◽  
pp. 21979-22006 ◽  
Author(s):  
Ghodsi Mohammadi Ziarani ◽  
Zahra Hassanzadeh ◽  
Parisa Gholamzadeh ◽  
Shima Asadi ◽  
Alireza Badiei
Keyword(s):  
Click Chemistry ◽  
Organic Synthesis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition

Click chemistry is undoubtedly the most powerful 1,3-dipolar cycloaddition reaction in organic synthesis.

scholarly journals "Click" chemistry as a tool to create novel biomaterials: a short review

2017 ◽  
Vol 1 (1) ◽  
pp. 22-34
Author(s):  
Mariana Barbosa ◽  
Cristina Martins ◽  
Paula Gomes
Keyword(s):  
Click Chemistry ◽  
Biomedical Applications ◽  
Recent Literature ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Polymeric Materials ◽  
Short Review ◽  
Dipolar Cycloaddition ◽  
Functionalization Of Polymers ◽  
Grafting Modification

In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

Advances in 1,3-Dipolar Cycloaddition Reaction of Azides and Alkynes: A Prototype of “Click” Chemistry

ChemInform ◽  
2006 ◽  
Vol 37 (8) ◽  
Author(s):  
Qian Wang ◽  
Srinivas Chittaboina ◽  
Hannah N. Barnhill
Keyword(s):  
Click Chemistry ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition

scholarly journals "Click" chemistry as a tool to create novel biomaterials: a short review

2015 ◽  
Vol 1 (1) ◽  
pp. 22-34 ◽  
Author(s):  
Mariana Barbosa ◽  
Cristina Martins ◽  
Paula Gomes
Keyword(s):  
Click Chemistry ◽  
Biomedical Applications ◽  
Recent Literature ◽  
Click Reaction ◽  
Cycloaddition Reaction ◽  
Polymeric Materials ◽  
Short Review ◽  
Dipolar Cycloaddition ◽  
Functionalization Of Polymers ◽  
Grafting Modification

In recent years, there has been a growing demand for novel strategies for biomedical applications. Chitosan is a typical cationic amino-containing polysaccharide that has been widely used due to its unique properties. The grafting modification of chitosan has been explored as an interesting method to develop multifunctional novel chitosan hybrid materials for drug delivery, tissue engineering, and other biomedical applications. Recently, “click” chemistry has been introduced into the synthesis of polymeric materials with well-defined and complex chain architectures. The Huisgen’s 1,3-dipolar cycloaddition reaction between alkynes and azides yielding triazoles is the principal example of a “click” reaction. Bioconjugation, surface modification, and orthogonal functionalization of polymers were successfully performed through this chemoselective reaction. In recent literature interest has been shown in this cycloaddition for the modification of polysaccharides, however, only a few chitosan graft copolymers have been synthesized by this technique.

scholarly journals HUISGEN AND HIS ADVENTURES IN A PLAYGROUND OF MECHANISMS AND NOVEL REACTIONS

Química Nova ◽  
2020 ◽  
Author(s):  
Daniel Gonzaga ◽  
Luana Forezi ◽  
Carolina Lima ◽  
Patricia Ferreira ◽  
Fernando Silva ◽  
...  
Keyword(s):  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Cycloaddition Reaction ◽  
Professor Emeritus ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
University Of Munich ◽  
The University

The death of professor Rolf Huisgen (1920-2020) was announced on March 26th 2020, in the midst of the COVID-19 pandemic. Professor Huisgen was professor emeritus at the University of Munich in Germany, and studied in detail the mechanism of the 1,3-dipolar cycloaddition reaction, significantly expanding its scope. Even though he did not discover this reaction, it was through his studies that it became important in organic synthesis. Indeed, in honor of his work, the reaction became known as Huisgen’s cycloaddition and it has been consolidated as a useful method for the preparation of five-membered heterocyclic compounds. Considering these facts, in this review we provide an overview on the applications of 1,3-dipolar cycloaddition reactions, starting with the seminal examples in the field and further discussing the most recent applications.

When CuAAC 'Click Chemistry' goes heterogeneous

2016 ◽  
Vol 6 (4) ◽  
pp. 923-957 ◽  
Author(s):  
S. Chassaing ◽  
V. Bénéteau ◽  
P. Pale
Keyword(s):  
Heterogeneous Catalysis ◽  
Green Chemistry ◽  
Click Chemistry ◽  
Organic Synthesis ◽  
Copper Ions ◽  
Cycloaddition Reaction ◽  
Catch Up

Within the green chemistry context, heterogeneous catalysis is more and more applied to organic synthesis. The well known ‘click chemistry’ and especially its flagship, the copper-catalyzed azide–alkyne cycloaddition reaction (CuAAC), is now catch up by such heterogenisation process and copper ions or metals have been grafted or deposited on or into various solids, such as (bio)polymers, charcoal, silica, zeolites, POM or MOF.

Synthesis of Self-assembling Cyclic Peptide-polymer Conjugates using Click Chemistry

2010 ◽  
Vol 63 (8) ◽  
pp. 1169 ◽  
Author(s):  
Robert Chapman ◽  
Katrina A. Jolliffe ◽  
Sébastien Perrier
Keyword(s):  
Click Chemistry ◽  
Self Assembly ◽  
Cyclic Peptide ◽  
Raft Polymerization ◽  
Cycloaddition Reaction ◽  
Polymer Chains ◽  
Dipolar Cycloaddition ◽  
Molecular Weights ◽  
Polymer Conjugates ◽  
Self Assembling

Self-assembling cyclic peptide-polymer conjugates were prepared by ‘clicking’ polymers (prepared by RAFT polymerization) to an azide functionalized d-alt-l cyclic octapeptide via the Huisgen 1,3-dipolar cycloaddition reaction. Due to the high graft density, the efficiency of the click chemistry conjugation reaction was found to be highly dependent on the size of the polymer. At relatively low molecular weights, as many as four polymer chains could be grafted to each 8 residue cyclic peptide ring. Evidence for the self assembly of the conjugates into peptide-polymer nanotubes was observed by TEM and IR.

A THEORETICAL STUDY ON THE MECHANISM OF 2:1 1, 3 DIPOLAR CYCLOADDITION REACTIONS

2007 ◽  
Vol 06 (04) ◽  
pp. 861-867 ◽  
Author(s):  
JING-FANG WANG ◽  
DONG-QING WEI ◽  
CHUN-FANG WANG ◽  
YONG YE ◽  
YI-XUE LI ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Organic Synthesis ◽  
Density Functional ◽  
Theoretical Study ◽  
Cycloaddition Reaction ◽  
Density Functional Theory Calculations ◽  
Biologically Active ◽  
Dipolar Cycloaddition ◽  
Functional Theory ◽  
Nitrile Oxides

The reactions between nitrile oxides and alkenes are of considerable interest in organic synthesis as the resulting heterocycles are versatile intermediates for the synthesis of natural products and biologically active compounds. In this paper, we design a series of reactions of phosphonyl nitrile oxides with acrylonnitrile, which can give 2:1 cycloaddition products with no crystal structure released so far, and present a detailed theoretical study on the mechanism of the 2:1 1, 3-dipolar cycloaddition reaction, which has been explored with density functional theory calculations at B3LYP/6-31G* level. The results reveal that the following mechanism is quite possible. Firstly, it starts as a normal 1,3-dipolar cycloaddition reaction to produce a regiospecific 1:1 product. Subsequently, highly reactive diisopropanyl phosphonyl nitrile oxide sequentially reacts with the aforementioned regiospecific 1:1 product and gives the corresponding cycloadduct. Further study is underway to expand the scope of this methodology, as well as to ascertain mechanistic details of the cycloaddition process.

New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Miron Teodor Caproiu ◽  
Florea Dumitrascu ◽  
Mino R. Caira
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridazine Derivatives ◽  
New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

Copper-catalyzed Convenient Synthesis and SAR Studies of Substituted-1,2,3-triazole as Antimicrobial Agents

2018 ◽  
Vol 16 (1) ◽  
pp. 3-10
Author(s):  
Aniket P. Sarkate ◽  
Kshipra S. Karnik ◽  
Pravin S. Wakte ◽  
Ajinkya P. Sarkate ◽  
Ashwini V. Izankar ◽  
...  
Keyword(s):  
Antimicrobial Activity ◽  
Antifungal Activity ◽  
Antimicrobial Agents ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Triazole Derivatives ◽  
Sar Studies ◽  
Convenient Synthesis ◽  
Antibacterial And Antifungal

Background:A novel copper-catalyzed synthesis of substituted-1,2,3-triazole derivatives has been developed and performed by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The reaction is one-pot multicomponent.Objective:We state the advancement and execution of a methodology allowing for the synthesis of some new substituted 1,2,3-triazole analogues with antimicrobial activity.Methods:A series of triazole derivatives was synthesized by Huisgen 1,3-dipolar cycloaddition reaction of azides with alkynes. The structures of the synthesized compounds were elucidated and confirmed by 1H NMR, IR, MS and elemental analysis. All the synthesized compounds were tested for their antimicrobial activity against a series of strains of Bacillus subtilis, Staphylococcus aureus and Escherichia coli for antibacterial activity and against the strains of Candida albicans, Aspergillus flavus and Aspergillus nigar for antifungal activity, respectively.Results and Conclusion:From the antimicrobial data, it was observed that all the newly synthesized compounds showed good to moderate level of antibacterial and antifungal activity.

Polar Diels-Alder Reactions Under Microwave Irradiation Employing Different Heterocyclic Compounds as Electrophiles

2019 ◽  
Vol 16 (6) ◽  
pp. 527-543 ◽  
Author(s):  
Pedro M.E. Mancini ◽  
Carla M. Ormachea ◽  
María N. Kneeteman
Keyword(s):  
Organic Synthesis ◽  
Heterocyclic Compounds ◽  
Ionic Conduction ◽  
Theoretical Calculations ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
The Other ◽  
Conventional Heating ◽  
Protic Ionic Liquids ◽  
Solvent Free Conditions

During the last twenty years, our research group has been working with aromatic nitrosubstituted compounds acting as electrophiles in Polar Diels-Alder (P-DA) reactions with different dienes of diverse nucleophilicity. In this type of reaction, after the cycloaddition reaction, the nitrated compounds obtained as the [4+2] cycloadducts suffer cis-extrusion with the loss of nitrous acid and a subsequent aromatization. In this form, the reaction results are irreversible. On the other hand, the microwave-assisted controlled heating become a powerful tool in organic synthesis as it makes the reaction mixture undergo heating by a combination of thermal effects, dipolar polarization and ionic conduction. As the Diels-Alder (D-A) reaction is one of the most important process in organic synthesis, the microwave (MW) irradiation was applied instead of conventional heating, and this resulted in better yields and shorter reaction times. Several substituted heterocyclic compounds were used as electrophiles and different dienes as nucleophiles. Two experimental situations are involved: one in the presence of Protic Ionic Liquids (PILs) as solvent and the other under solvent-free conditions. The analysis is based on experimental data and theoretical calculations.

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