A practical flow synthesis of 1,2,3-triazoles

Abstract

Copper-on-charcoal is an excellent heterogeneous catalyst for the alkyne–azide cycloaddition reaction performed under continuous flow conditions. 2-Ynoic acids undergo decarboxylation/cycloaddition cascade giving triazoles bearing small alkyl chains.

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

“…A robust and versatile protocol was reported by Drelinkiewicz et al for the continuous flow synthesizing 1,4-di-substituted 1,2,3-triazoles utilizing copper-on-charcoal as a heterogeneous catalyst, as depicted in Table 2, entry (21). 89 This methodology allowed for synthesizing a diverse set of substituted 1,2,3-triazoles with good functional group tolerance and high yields. Notably, the reaction did not require the addition of a base.…”

Stereochemical and Computational NMR Survey of 1,2,3-Triazoles: in Search of the Original Tauto-Conformers

“…The derivatives of azoles, in particular, 1,2,3-triazoles hold a special place in heterocyclic chemistry and find extensive applications in diverse fields of agriculture, materials science, chemical biology, and medicinal chemistry. Readily available 1,2,3-triazoles, with a wide range of various activities, have long been used as high-energy materials, ionic liquids, medicinal products, radiosensitizers, universal bases in peptide nucleic acids, plasticizers, dyes, plant growth regulators, pesticides and herbicides, synthons for fine organic synthesis, and precursors for nanocomposites. − 1,2,3-Triazole derivatives are successfully employed to create numerous drug scaffolds exhibiting anti-HIV, anticancer, antiviral, antibacterial, anti-inflammatory, antiproliferative, aticholinesterase, antioxidant, antifungal activity, etc. ,− ,,,− ,− The therapeutic effects of many compounds containing a 1,2,3-triazole moiety are also well-known.…”

“…The 1,2,3-triazole moiety is of great importance for organic, bioorganic, and medicinal chemistry due to its unique properties, high chemical stability (inert nature), large dipole moment, tautomeric transformations, high systematicity, and ability to mimic various functional groups, especially amide fragments. ,,,,,− This motif is ubiquitous in experimental drug candidates and approved pharmaceuticals. Moreover, the presence of three consecutive sp 2 nitrogen atoms imparts the 1,2,3-triazole ring with a special (high) electron-donating ability. , …”

Design and synthesis of Meldrum's acid based 7-azaindole anchored 1,2,3-triazole hybrids as anticancer agents

“…14 In addition, 7-azaindole is the chromophoric moiety of 7-azatryptophan, which is an alternative to tryptophan as an optical probe of protein structure and dynamics. 15 The 1,2,3-triazole moiety is found to have a wide range of biological properties, such as antibacterial, 16 antifungal, 17 antitubercular, 18 antiviral, 19 anticancer, 20 anti-inflammatory, 21 antiepileptic, 22 analgesic, 23 anti-Parkinson's, 24 and antidepressant, 25 as well as versatile scaffolding. Additionally, several medications that contain 1,2,3-triazole scaffolds are currently being used in clinical settings, including Cefatrizine (an antibiotic), Carboxyamidotriazole (an anti-cancer agent), TSAO (an anti-HIV agent) and Tazobactam (an anti-bacterial agent).…”