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The present review narrates several reports which deal with the synthesis of fused 1,2,3-triazole containing scaffolds following a sequential multicomponent reaction (MCR)—intramolecular azide-alkyne cycloaddition (IAAC) approach. The reviewed reactions were cleverly designed so as to incorporate azide and alkyne functionalities in the MCR product which was then subjected to IAAC. The review is divided into two sections based on the number of components in the multicomponent reaction. We have aimed at a critical discussion and also have highlighted either advantages or disadvantages of each methodology.

A practical three-step protocol for the assembly of triazolobenzodiazepine-fused diketopiperazines and hydantoins has been developed. The synthesis of these tetracyclic ring systems was initiated by an Ugi reaction, which brought together all necessary functionalities for further transformations. The Ugi adducts were then subjected to a base-induced ring closing and an intramolecular azide–alkyne cycloaddition reaction in succession to obtain highly fused benzodiazepine frameworks.

The crown-containing bis(chromophoric) chemosensor for mercury(II) cations in an aqueous solution was synthesized using the azide—alkyne 1,3-dipolar cycloaddition click reaction. The synthesized compound contains the 4-methoxy-1,8-naphthalimide fragment acting as the electron excitation energy donor and styrylpyridine being the chromorphore-acceptor. Upon the excitation of the naphthalimide residue with the visible light, the resonance energy transfer (RET) occurs, and its efficiency decreases as a result of complex formation with Hg 2+ cations. The changes in the fluorescence spectrum observed upon the addition of Hg 2+ allow one to detect the ratiometric fluorescence response due to an increase in the ratio of emission intensities in the donor and acceptor channels. Based on the spectrophotometric and spectrofluorimetric titration data, the logarithms of the stability constants (log K ) for the 1 : 1 metal—ligand complex were calculated to be 5.37±0.05 and 5.81±0.06, respectively. The proposed fluoroionophore is characterized by the detection limit of Hg 2+ ions in water at pH 4.5 equal to 40 nmol L −1 . The ability of the synthesized chemosensor to perform fluorescence imaging of mercury(II) cations in living cells was also analyzed.

We report herein on a new platform for synthesizing stable, inert, and dispersible metal-free single-chain nanoparticles (SCNPs) via intramolecular metal-traceless azide–alkyne click chemistry. It is well known that SCNPs synthesized via Cu(I)-catalyzed azide–alkyne cycloaddition (CuAAC) often experience metal-induced aggregation issues during storage. Moreover, the presence of metal traces limits its use in a number of potential applications. To address these problems, we selected a bifunctional cross-linker molecule, sym-dibenzo-1,5-cyclooctadiene-3,7-diyne (DIBOD). DIBOD has two highly strained alkyne bonds that allow for the synthesis of metal-free SCNPs. We demonstrate the utility of this new approach by synthesizing metal-free polystyrene (PS)-SCNPs without significant aggregation issues during storage, as demonstrated by small-angle X-ray scattering (SAXS) experiments. Notably, this method paves the way for the synthesis of long-term-dispersible, metal-free SCNPs from potentially any polymer precursor decorated with azide functional groups.