Ligand‐free, copper‐catalyzed, one‐pot, three‐component synthesis of novel 1,2,3‐triazole‐linked indoles in magnetized water

Abstract

Magnetized water (MW) is used as a green and new solvent-promoting medium for the one-pot, three-component synthesis of novel 1,2,3-triazole-linked indoles catalyzed by copper iodide. A broad range of 2-aryl-1-(prop-2-ynyl)-1H-indole-3-carbaldehydes were reacted with alkyl halides and sodium azide via coppercatalyzed azide-alkyne cycloaddition reactions in MW in the absence of any ligand. This method offers the advantages of short reaction times, green procedure, low cost, simple work-up, quantitative reaction yields, and no need for any organic solvent.

Exploring recent developments on 1,2,4‐triazole: Synthesis and biological applications

“…The reaction between 2‐aryl‐1‐(prop‐2‐ynyl)‐1 H ‐indole‐3‐carbaldehydes with alkyl halides and sodium azide undergoes azide‐alkyne cycloaddition. The green nature of the method, modest work‐up, short reaction time, good yield, and the absence of organic solvents are some of the highlights of this reaction (Scheme ) …”

Synthesis of aryl‐functionalized, 1,5‐disubstituted 1,2,3‐triazoles and derivatives by arylation of zwitterionic ruthenium triazolato complexes

“…The 1,2,3-triazole nucleus, one of the most important nitrogen-rich heterocycles, has found widespread applications in agricultural, [1][2][3] pharmacological [4,5] and material [6,7] chemistry due to their diverse activity, hydrogen bond donating and accepting abilities [8,9] which can be favorable in the binding of DNA/biomolecular targets and displaying significant biological and pharmacological properties that including antibacterial, anti-inflammatory, antiviral, antifungal, anticancer, and so on. [10] Since the publication of "click" reactions in 2001, [11] the chemistry of triazole and derivatives thereof have been extensively studied and tested, and numerous reports dealing with copper-catalyzed azide-alkyne cycloaddition (CuAAC) [12][13][14] to give the 1,4-disubstituted and ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC) [15] reactions to give the 1,5-disubstituted 1,2,3-triazoles have appeared and a variety of 1,2,3-triazoles and derivatives have been widely applied in the pharmaceutical industry [4,5,16,17] during the past two decades. It is worth noting that the aromatic substituents on these triazole drugs play a crucial role because of their diverse biological activities resulting from the aromatic non-covalent interactions such as πÁÁÁπ stacking and aromatic C-HÁÁÁπ interactions toward DNA, RNA, nucleic acids and other biomolecules.…”

Zinc Oxide Nanoparticles as Efficient Heterogeneous Catalyst for Synthesis of Bio‐active Heterocyclic Compounds

“…Due to their high surface‐to‐volume ratios and highly active surface atoms, nanocatalysts are a promising alternative to conventional [56–60] . Nanocatalysts are of great importance in the context of environmentally conscious science, and in particular for catalysis, due to their nanocatalysts′ effectiveness [61–67] as a coating on silicate, aluminium oxide, titanium dioxide, fiberglass, ceramics, and activated carbon has been the subject of several research during the past decade [46,68–75] . Nanocatalysts are now widely used to produce heterocyclic compounds [76] .…”

“…[56][57][58][59][60] Nanocatalysts are of great importance in the context of environmentally conscious science, and in particular for catalysis, due to their nanocatalysts' effectiveness [61][62][63][64][65][66][67] as a coating on silicate, aluminium oxide, titanium dioxide, fiberglass, ceramics, and activated carbon has been the subject of several research during the past decade. [46,[68][69][70][71][72][73][74][75] Nanocatalysts are now widely used to produce heterocyclic compounds. [76] Herein, we discuss the most recent (2012 to present) nano-catalytic synthesis of highly substituted heterocycles.…”