Cyclodextrin Methacrylate via Microwave-Assisted Click Reaction

Abstract

Click reaction of propargyl methacrylate (1) with 6I-azido-6I-deoxycyclomaltoheptaose (2) was carried out to synthesize mono-(1H-1,2,3-triazol-4-yl)(methyl)2-methylacryl-β-cyclodextrin (3). The process was investigated by varying the reaction time, temperature profiles, and copper catalyst. Microwave irradiation was compared with conventional heating. The microwave-assisted Cu(I)-catalyzed cycloaddition affords the complete conversion of (2) into 1,4-disubstituted triazole in a significant decreased reaction time. Under microwave conditions, the cycloaddition of (2) onto poly(propargyl methacrylate) (5) was conducted in excellent yields. The regioselectivity of click reactions in dependence of reaction conditions was evaluated by use of NMR spectroscopy. The reactions performed under microwave conditions led exclusively to 1,4-disubstituted triazole, while the conventional heating led to a regioisomeric mixture.

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

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Inclusion and Functionalization of Polymers with Cyclodextrins: Current Applications and Future Prospects

“…The CD content of the copolymer can be controlled by varying the comonomer content [20]. Munteanu et al [21] synthesized such polymerizable CD monomers via a "click chemistry" route leading to a ring-like supramolecular structure. Copper(I)-catalyzed Huisgen type 1,3-dipolar cycloadition of azides and alkynes extended its area of application.…”

One Decade of Microwave‐Assisted Polymerizations: Quo vadis?

“…Ritter and coworkers prepared polymerizable cyclodextrin monomethacrylates by conventional and microwave-assisted heating in a CEM Discover device. [30] They stated that microwave-assisted heating was an efficient synthetic approach, providing structural control and decreasing the reaction times; polymerization of the cyclodextrin methacrylates yielded (water-soluble) oligomers (Scheme 1).…”

“…Influence of microwave-assisted and conventional conditions on the regioselectivity of cyclodextrin methacrylate synthesis [according to ref. [30] ].…”