Fluorescent 7-azaindoleN-linked 1,2,3-triazole: synthesis and study of antimicrobial, molecular docking, ADME and DFT properties

Abstract

Two libraries of biologically essential and fluorescent 7-azaindole N-linked benzyl 1,2,3-triazole (4a-4i) and 7-azaindole N-linked phenyl 1,2,3-triazole (4j-4q) hybrids have been designed and synthesized from N-propargyl 7-azaindole, i.e., 1-prop-2-ynyl-1H-pyrrolo[2,3-b]pyridine (2)...

Green synthesis of 1,4-disubstituted 1,2,3-triazoles: a sustainable approach

“…Additionally, Woo and his team reported a novel binuclear copper(II)-oxalate complex with DMP as a competent catalyst for a three-component 1,3-dipolar cycloaddition CuAAC reaction, as illustrated in Table 1, entry (11) to produce 1,4-disubstituted 1,2,3-triazoles with excellent yields, utilizing aromatic halides, sodium azide, and acetylene in green media such as water with a low catalyst dosage. 55 Anvari and Shadjou presented a one-pot efficient synthesis of 1,4-disubstituted 1,2,3-triazoles in water, utilizing Cu@KCC-1-NH-CS 2 as a novel nanoreactor, 56 as shown in Table 1, entry (12). The advantages of this approach leveraged the high surface area and porous structure of the nano-catalyst, enabling excellent catalytic performance with short reaction times, easy workup, absence of toxic solvents, and catalytic reusability.…”

“…This approach involved aryl boronic acids, sodium azide, and alkynes under micellar conditions, with an aqueous bile salt NaDC (sodium deoxychlorate) solution serving as an environment-friendly accelerating medium. The method aimed to enhance the green credentials of CuAAC reactions, as in Table 2, entry (12). 80 Zhao and colleagues focused on a one-pot, three-component reaction involving organic halides, terminal acetylenes, and sodium azide for the synthesis of various 1,4-disubstituted 1,2,3-triazoles derivatives by employing CuI and Et 2 NH as a new catalytic system in glycerol as a green reaction solvent at rt 81 as shown in Table 2, entry (13).…”

“…The experiment was conducted under standard temperature and pressure conditions, utilizing environmentally benign solvents. 150 In a supramolecular ensemble, Cu 2 O-Ag NPs and aggregates of perylene bisimide (PBI) developed by Singh et al facilitated a one-pot three-component click reaction to yield 1,4-disubstituted 1,2,3-triazoles under green conditions at rt, as depicted in Table 5, entry (12). 151 Remarkably, a "dip strip", created by dip coating a filter paper strip with the supramolecular ensemble solution, served as an efficient hetero-catalytic system for the one-pot, three-component reaction.…”

“…This environment-friendly approach, depicted in Table 7, entry (11), 188 demonstrated high yields and reflected a commitment to sustainability in synthesis methodologies. Chouaib and his team had synthesized various analogs of maslinic acid as a core and various aromatic azides as a regiospecific synthesis of 1,4-triazolyl derivatives were described by Cu(I) catalyzed alkyne-azide cycloaddition, assisted by µw irradiation (green chemistry condition) avoiding toxic reagents and solvents with quantitative yields and shorter reaction time than convention method, as shown in Table 7, entry (12). 189 Souza et al reported a general methodology for synthesizing a one-pot, three-component 1,4disubstituted 1,2,3-triazoles involving imine that reacted with in situ organoazides by Cu-catalysed [3 + 2] AAC reaction in ACN solvent using µw-assisted reaction conditions, as depicted in Table 7, entry (13).…”

A selective chemosensor via click chemistry for Cu2+ and Hg2+ ions in organic media

“…The synthesis of 1,2,3-triazole-based sensors involves the modification of the 1,2,3-triazole ring to introduce functional groups that can interact with metal ions. 14 The improvement can be achieved through synthetic routes, including “click” chemistry, 9,15–17 azide–alkyne cycloaddition, 18,19 and Sonogashira coupling reactions. 20–22 “Click” chemistry is a powerful tool for synthesizing 1,2,3-triazole-based sensors.…”