5301-97-3

Upstream product

• 1777-55-5 (4-methoxyphenacylidene)triphenyl phosphorane 
• 768-60-5 4-methoxyphenylacetylen 
• 1028975-99-6 C₂₃H₂₂N₆O₆ 
• 4648-54-8 trimethylsilylazide 
• 872700-71-5 [4-(4-methoxyphenyl)-1,2,3-triazol-1-yl]methyl pivalate 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 6595-28-4 2-azido-1-(4-methoxyphenyl)ethan-1-one 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 32117-52-5 1-(1-(4-methoxyphenyl)ethylidene)-2-tosylhydrazine 
• 3179-10-0 (E)-1-methoxy-4-(2-nitrovinyl)benzene 
• 75-52-5 nitromethane 
• 123-11-5 4-methoxy-benzaldehyde 
• 1210046-27-7 2-(4-(4-methoxyphenyl)-1H-1,2,3-triazol-1-yl)-1-phenylethan-1-one 
• 3179-10-0 1-methoxy-4-(2-nitro-vinyl)-benzene 

Downstream Products

• 89221-21-6 4-(4-hydroxyphenyl)-1,2,3-triazole 

Relevant academic research and scientific papers

Copper-Catalyzed Azide-Alkyne Cycloaddition of Hydrazoic Acid Formed in Situ from Sodium Azide Affords 4-Monosubstituted-1,2,3-Triazoles

We report a copper-catalyzed cycloaddition of hydrogen azide (hydrazoic acid, HN3) with terminal alkynes to form 4-substituted-1H-1,2,3-triazoles in a sustainable manner. Hydrazoic acid was formed in situ from sodium azide under acidic conditions to react with terminal alkynes in a copper-catalyzed reaction. Using polydentate N-donor chelating ligands and mild organic acids, the reactions were realized to proceed at room temperature under aerobic conditions in a methanol-water mixture and with 5 mol % catalyst loadings to afford 4-substituted-1,2,3-triazoles in high yields. This method is amenable on a wide range of alkyne substrates, including unprotected peptides, showing diverse functional group tolerance. It is applicable for late-stage functionalization synthetic strategies, as demonstrated in the synthesis of the triazole analogue of losartan. The preparation of orthogonally protected azahistidine from Fmoc-l-propargylglycine was realized on a gram scale. The hazardous nature of hydrazoic acid has been diminished as it forms in situ in a reactive species in the copper-catalyzed reaction.

Direct Synthesis of 4-Aryl-1,2,3-triazoles via I2-Promoted Cyclization under Metal- And Azide-Free Conditions

We herein report an iodine-mediated formal [2 + 2 + 1] cyclization of methyl ketones, p-toluenesulfonyl hydrazines, and 1-aminopyridinium iodide for preparation of 4-aryl-NH-1,2,3-triazoles under metal- and azide-free conditions. Notably, this is achieved

Dipolar HCP materials as alternatives to DMF solvent for azide-based synthesis

Hypercrosslinked polymers HCP-DMF and HCP-DMF-SO3H containing abundant and flexible DMF moieties were designed and synthesized. Benefitting from the solvation microenvironment provided by the pseudo-DMF moities, the polar HCPs manifested outstanding performances in the conversions of NaN3 to benzylic azides and 1,2,3-triazoles in EtOH (95%), respectively, avoiding the use of risky DMF and improving the separation processes of the products.

Silica immobilized copper N-heterocyclic carbene: An effective route to 1,2,3-triazoles via azide-alkyne cycloaddition and multicomponent click reaction

A new silica supported copper N-heterocyclic carbene (Cu-NHC@SiO2) complex is prepared and characterized by scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDX) and X-ray photoelectron spectroscopy (XPS) analyses. This complex is an efficient and easily retrievable catalyst for 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition reaction as well as one-pot reaction using arylboronic acids. This catalytic system is also suitable for synthesis of 4-aryl-NH-1,2,3-triazoles from diverse benzaldehydes. Further, the catalyst can efficiently be recycled up to fifth cycle for all the three methods of 1,2,3-triazole synthesis through direct azide-alkyne cycloaddition and multi-component reactions.

Access to (Z)-β-Substituted Enamides from N1-H-1,2,3-Triazoles

A direct ring-opening/nucleophilic substitution reaction of N1-H-1,2,3-triazoles has been described. Divergent (Z)-β-halogen- or sulfonyl-substituted enamides could be stereospecifically synthesized in a tunable manner. This strategy might not only enable

Sulfonic acid-functionalized magnetic carbon nitride as highly efficient ionic composite for sustainable assembly of 1,2,3-triazoles

Abstract: An efficient and straightforward method for constructing of biologically active 4-aryl-NH-1,2,3-triazoles by the 1,3-dipolar cycloaddition reaction of β-nitrostyrene?and sodium azide in the presence of acidic graphitic carbon nitride (Fe3/

A green metal-free "one-pot" microwave assisted synthesis of 1,4-dihydrochromene triazoles

The synthesis of several 4-aryl-1,4-dihydrochromene-triazoles was achieved via a metal-free "one-pot"procedure using PEG400 as the sole solvent in an eco-friendly process. Using microwave irradiation, the triazole derivatives were obtained in good yields and short reaction times starting from readily accessible building blocks.

Cu-Catalyzed Site-Selective and Enantioselective Ring Opening of Cyclic Diaryliodoniums with 1,2,3-Triazoles

A Cu-catalyzed enantioselective ring-opening/triazolylation reaction is reported. The reaction shows excellent chemoselectivity regarding the three different nitrogen atoms of 1,2,3-triazoles. The optically enriched axially chiral aryl iodides thus obtained were readily derivatized to different types of chiral phosphine ligands and their corresponding copper or palladium complexes.

Iodine-Mediated Condensation–Cyclization of α-Azido Ketones with p-Toluenesulfonyl Hydrazide for Synthesis of 4-Aryl-NH-1,2,3-Triazoles

A molecular iodine mediated condensation–cyclization reaction for the synthesis of 4-aryl-NH-1,2,3-triazoles has been developed from readily available α-azido acetophenones and p-toluenesulfonyl hydrazide. This reaction provides a metal-free strategy for the sequential formation of C–N and N–N bonds in mild condition.

Fluorescent 5-Pyrimidine and 8-Purine Nucleosides Modified with an N-Unsubstituted 1,2,3-Triazol-4-yl Moiety

The Cu(I)- or Ag(I)-catalyzed cycloaddition between 8-ethynyladenine or guanine nucleosides and TMSN3 gave 8-(1-H-1,2,3-triazol-4-yl) nucleosides in good yields. On the other hand, reactions of 5-ethynyluracil or cytosine nucleosides with TMSN3 led to the chemoselective formation of triazoles via Cu(I)-catalyzed cycloaddition or vinyl azides via Ag(I)-catalyzed hydroazidation. These nucleosides with a minimalistic triazolyl modification showed excellent fluorescent properties with 8-(1-H-1,2,3-triazol-4-yl)-2′-deoxyadenosine (8-TrzdA), exhibiting a quantum yield of 44%. The 8-TrzdA 5′-triphosphate was incorporated into duplex DNA containing a one-nucleotide gap by DNA polymerase β.