ChemInform Abstract: Diels-Alder “Click” Reactions

ChemInform ◽  
2016 ◽  
Vol 47 (49) ◽  
Author(s):  
Dajana Gaso-Sokac ◽  
Marija Stivojevic
Keyword(s):  
Diels Alder ◽  
Click Reactions

scholarly journals Multifunctional and Transformable ‘Clickable’ Hydrogel Coatings on Titanium Surfaces: From Protein Immobilization to Cellular Attachment

Polymers ◽  
2020 ◽  
Vol 12 (6) ◽  
pp. 1211
Author(s):  
Tugce Nihal Gevrek ◽  
Aysun Degirmenci ◽  
Rana Sanyal ◽  
Amitav Sanyal
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Click Reactions ◽  
Ene Reaction ◽  
Diels Alder Reaction ◽  
Cellular Attachment ◽  
Wide Range ◽  
Hydrogel Coatings ◽  
Titanium Surfaces ◽  
Maleimide Group

Multifunctionalizable hydrogel coatings on titanium interfaces are useful in a wide range of biomedical applications utilizing titanium-based materials. In this study, furan-protected maleimide groups containing multi-clickable biocompatible hydrogel layers are fabricated on a titanium surface. Upon thermal treatment, the masked maleimide groups within the hydrogel are converted to thiol-reactive maleimide groups. The thiol-reactive maleimide group allows facile functionalization of these hydrogels through the thiol-maleimide nucleophilic addition and Diels–Alder cycloaddition reactions, under mild conditions. Additionally, the strained alkene unit in the furan-protected maleimide moiety undergoes radical thiol-ene reaction, as well as the inverse-electron-demand Diels–Alder reaction with tetrazine containing molecules. Taking advantage of photo-initiated thiol-ene ‘click’ reactions, we demonstrate spatially controlled immobilization of the fluorescent dye thiol-containing boron dipyrromethene (BODIPY-SH). Lastly, we establish that the extent of functionalization on hydrogels can be controlled by attachment of biotin-benzyl-tetrazine, followed by immobilization of TRITC-labelled ExtrAvidin. Being versatile and practical, we believe that the described multifunctional and transformable ‘clickable’ hydrogels on titanium-based substrates described here can find applications in areas involving modification of the interface with bioactive entities.

Thermally Reversible Dendronized Step-Polymers Based on Sequential Huisgen 1,3-Dipolar Cycloaddition and Diels−Alder “Click” Reactions

2010 ◽  
Vol 43 (3) ◽  
pp. 1270-1276 ◽  
Author(s):  
Nathan W. Polaske ◽  
Dominic V. McGrath ◽  
James R. McElhanon
Keyword(s):  
Diels Alder ◽  
Dipolar Cycloaddition ◽  
Click Reactions

scholarly journals Role of Click Chemistry in Organic Synthesis

2021 ◽  
Author(s):  
Ayushi Sethiya ◽  
Nusrat Sahiba ◽  
Shikha Agarwal
Keyword(s):  
Click Chemistry ◽  
Organic Synthesis ◽  
Material Science ◽  
Diels Alder ◽  
Organic Reactions ◽  
Ene Reactions ◽  
Click Reactions ◽  
Ring Opening Reactions ◽  
Nucleophilic Ring Opening

Click chemistry involves highly efficient organic reactions of two or more highly functionalized chemical entities under eco-benign conditions for the synthesis of different heterocycles. Several organic reactions such as nucleophilic ring-opening reactions, cyclo-additions, nucleophilic addition reactions, thiol-ene reactions, Diels Alder reactions, etc. are included in click reactions. These reactions have very important features i.e. high functional group tolerance, formation of a single product, high atom economy, high yielding, no need for column purification, etc. It also possesses several applications in drug discovery, supramolecular chemistry, material science, nanotechnology, etc. Being highly significant and valuable, we have elaborated on several aspects of click reactions in organic synthesis in this chapter. Recent advancements in the field of organic synthesis using click chemistry approach have been deliberated by citing last five years articles.

Diels-Alder “Click” Reactions

2016 ◽  
Vol 20 (21) ◽  
pp. 2211-2221 ◽  
Author(s):  
Dajana Ga.so-Soka.c ◽  
Marija Stivojevi.c
Keyword(s):  
Diels Alder ◽  
Click Reactions

Biomimetic total syntheses of baefrutones A–D, baeckenon B, and frutescones A, D–F

2020 ◽  
Vol 18 (6) ◽  
pp. 1135-1139
Author(s):  
Ji-Qin Hou ◽  
Jiang-Hong Yu ◽  
Heng Zhao ◽  
Ying-Ying Dong ◽  
Qiu-Shi Peng ◽  
...  
Keyword(s):  
Michael Addition ◽  
Diels Alder ◽  
Total Syntheses ◽  
Click Reactions ◽  
First Time

Biomimetic total syntheses of the natural tasmanone-based meroterpenoids were achieved for the first time via Michael addition, oxidative [4 + 2] cycloaddition, and water-promoted Diels–Alder click reactions.

Synthesis and properties of couplable ABCDE star copolymers by orthogonal CuAAC and Diels–Alder click reactions

2016 ◽  
Vol 7 (8) ◽  
pp. 1603-1611 ◽  
Author(s):  
Huanhuan Liu ◽  
Weidong Pan ◽  
Min Tong ◽  
Youliang Zhao
Keyword(s):  
Diels Alder ◽  
Click Reactions ◽  
Star Copolymers

Well-defined ABCDE star quintopolymers generated by a modular and orthogonal strategy could self-assemble into intriguing nanoobjects sensitive to thermal and pH stimuli.

scholarly journals Structural and solvent control over activation parameters for a pair of retro Diels-Alder reactions

2019 ◽  
Vol 9 (1) ◽  
Author(s):  
Andrea L. Widstrom ◽  
Benjamin J. Lear
Keyword(s):  
Maleic Anhydride ◽  
Activation Parameters ◽  
Solvent Polarity ◽  
Alder Reaction ◽  
Diels Alder ◽  
Temperature Dependent ◽  
Experimental Conditions ◽  
Click Reactions ◽  
Solvent Dependence ◽  
Solvent Control

AbstractWe report the temperature dependent NMR of two Diels-Alder adducts of furan: one formed with maleic anhydride and the other with N-methylmaleimide. These adducts are the products of so-called ‘click’ reactions, widely valued for providing simple, reliable, and robust reactivity. Under our experimental conditions, these adducts undergo a retro Diels-Alder reaction and we use our temperature dependent NMR to determine the rates of these reactions at multiple temperatures—ultimately providing estimates of the activation parameters for the reversion. We repeat these measurements in three solvents. We find that, in all solvents, the barrier to reversion is larger for the adduct formed with N-methylmaleimide. The barrier to reversion for this adduct is relatively insensitive to changes in solvent while the adduct formed with maleic anhydride responds more strongly to changes in solvent polarity. The differences in reaction barrier and solvent dependence arises because the adduct formed with N-methylmalemide is more stable—leading to a larger barrier to reversion—while the adduct formed with maleic anhydride experiences a larger change in dipole during the reaction—leading to a larger solvent dependence.

Site-specific one-pot triple click labeling for DNA and RNA

2018 ◽  
Vol 54 (83) ◽  
pp. 11781-11784 ◽  
Author(s):  
Marie-Luise Winz ◽  
Eva Christina Linder ◽  
Juliane Becker ◽  
Andres Jäschke
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
One Pot ◽  
Site Specific ◽  
Click Reactions ◽  
Inverse Electron Demand ◽  
Dna And Rna ◽  
Diels Alder Reaction ◽  
Electron Demand

We report site-specific triple click labeling for DNA and RNA in a one-pot setup by performing inverse electron demand Diels–Alder reaction and strain-promoted and copper catalyzed click reactions sequentially.

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