Abstract
Among nitrogen-containing heterocyclic compounds, 1,2,3-triazoles are privileged structure motif and received a great deal of attention in academics and industry. Even though absent in nature, 1,2,3-triazoles have found broad applications in drug discovery, organic synthesis, polymer chemistry, supramolecular chemistry, bioconjugation, chemical biology, fluorescent imaging, and materials science. Therefore, the development of facile and straightforward methodology for the synthesis of 1,2,3-triazoles is of noteworthy interest. In this study, emphasis will be given to numerous synthetic approaches for the synthesis of 1,2,3-triazoles, especially the popular click chemistry approach. Furthermore, several biological activities of this promising heterocycle will also be discussed.
Highlights
Nitrogen-containing heterocyclic compounds are indispensable for life as they are part of essential building blocks like amino acids, nucleotides, etc. 1,2,3Triazoles are one of the most important nitrogen-containing five-membered heterocycles and have a wide range of applications in pharmaceuticals, supramolecular chemistry, organic synthesis, chemical biology and industry [1–6]
Rangappa and coworkers prepared a series of 1,2-benzisoxazole tethered 1,2,3triazoles 4 and established its noteworthy antiproliferative effect against human acute myeloid leukemia (AML) cells
Labadie and coworkers used click chemistry to synthesize a small library of 1,2,3-triazole derivatives and screened them against Mycobacterium tuberculosis and Mycobacterium avium
Summary
Nitrogen-containing heterocyclic compounds are indispensable for life as they are part of essential building blocks like amino acids, nucleotides, etc. 1,2,3Triazoles are one of the most important nitrogen-containing five-membered heterocycles and have a wide range of applications in pharmaceuticals, supramolecular chemistry, organic synthesis, chemical biology and industry [1–6]. The 1,2,3triazoles has numerous useful properties like high chemical stability (usually inert to acidic or basic hydrolysis as well as oxidizing and reducing conditions even at high temperature), aromatic character, strong dipole moment (4.8–5.6 Debye), and hydrogen bonding ability [7]. These spectacular features make the substituted 1,2,3triazole motif structurally resembling to the amide bond, mimicking an E or a Z amide bond. 2.2 Metal-catalyzed 1,3-dipolar cycloaddition In 2001, Sharpless et al coined the term “Click Chemistry,” a set of highly reliable, practical, and selective reactions for the rapid synthesis of valuable new compounds and combinatorial libraries. Sun and coworkers reported intermolecular iridium-catalyzed azide-alkyne cycloaddition reaction (IrAAC) of electron-rich internal alkynes [22]
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