A Click Reaction for Fluorescent Labelling: Application of the 1,3-Dipolar Cycloaddition Reaction

‘Click reactions’ are the copper catalysed dipolar cycloaddition reaction of azides and alkynes to incorporate nitrogens into a cyclic hydrocarbon scaffold forming a triazole ring. Owing to its efficiency and versatility, this reaction and the products, triazole-containing heterocycles, have immense importance in medicinal chemistry. Copper is the only known catalyst to carry out this reaction, the mechanism of which remains unclear. We report here that the ‘click reactions’ can also be catalysed by silver halides in non-aqueous medium. It constitutes an alternative to the well-known CuAAC click reaction. The yield of the reaction varies on the type of counter ion present in the silver salt. This reaction exhibits significant features, such as high regioselectivity, mild reaction conditions, easy availability of substrates and reasonably good yields. In this communication, the findings of a new catalyst along with the effect of solvent and counter ions will help to decipher the still obscure mechanism of this important reaction.

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

U Porto Journal of Engineering ◽

10.24840/2183-6493_001.001_0004 ◽

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.

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Simple, stepwise and alternative syntheses of indolyl triazoles via Huisgen,s 1, 3-dipolar cycloaddition reaction

Letters in Organic Chemistry ◽

10.2174/1570178617666200225110402 ◽

2020 ◽

Vol 17 ◽

Author(s):

Ch. Venkata Ramana Reddy ◽

G. Ganga Reddy

Keyword(s):

Reaction Time ◽

Addition Reaction ◽

Click Reaction ◽

Cycloaddition Reaction ◽

Sodium Ascorbate ◽

Dipolar Cycloaddition ◽

Spectroscopic Methods ◽

Aryl Azides ◽

Simple Processing ◽

High Yields

: A series of new 2-((1-((1-(4-methoxy-3-nitrophenyl)-1H-1,2,3-triazol-4-yl)methyl)1H-indol-3-yl)me thylene)malononitrile derivatives were synthesized by the 1,3 dipolar cyclo addition reaction (click reaction) of 2-((1-(prop-2-yn-1-yl)-1H-indol-3-yl)methylene)malononitrile with different aryl azides in the presence of sodium ascorbate and copper sulphate in good yields. The advantages of this method are efficient, clean, high yields, easy workup procedures and shorter reaction time. These reactions are very facile giving products by simple processing that does not require purification by column chromatography. All the newly synthesized compounds were confirmed by spectroscopic methods.

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

U Porto Journal of Engineering ◽

10.24840/10.24840/2183-6493_001.001_0004 ◽

2015 ◽

Vol 1 (1) ◽

pp. 22-34 ◽

Cited By ~ 2

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.

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

Revista de Chimie ◽

10.37358/rc.08.11.2011 ◽

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.

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

Letters in Drug Design & Discovery ◽

10.2174/1570180815666180326153322 ◽

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.

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