1101852-29-2

Upstream product

• 1280738-47-7 2-[2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethyl]-1H-isoindole-1,3(2H)-dione 
• 87156-40-9 1-amino-2-azidoethane 
• 536-74-3 phenylacetylene 

Relevant academic research and scientific papers

Tris-isocyanide copper(I) complex enabling copper azide-alkyne cycloaddition in neat conditions

The three-coordinated homoleptic Cu(I) complex with 2,6-dimethylphenyl isocyanide in the coordination sphere was easily synthesized and isolated as tetrafluoroborate salt. The structure of the compound was determined by single-crystal X-ray diffraction. T

New strategies for molecular diversification of 2-[Aminoalkyl-(1H-1,2,3-Triazol-1- yl)]-1,4-naphthoquinones using click chemistry

Click chemistry-based strategies for the synthesis of 2-Amino-Alkyl-1,2,3-Triazole-1,4- naphthoquinone derivatives make it possible to obtain desired products from 1,4-naphthoquinone (1,4-NQ), and bio-based lawsone, nor-lapachol and lapachol. The first route (Strategy A) starting from 1,4-NQ and amino alcohols, then 2-Amino-Alkyl-1,4-NQ alcohols, were tosylated. The azide ion displaced the tosylate group to afford 2-Azide-Alkyl-1,4-NQ, which was submitted to a copper-catalyzed azide alkyne cycloaddition (CuAAC) condition. The triazole-naphthoquinones were obtained in an overall yield of roughly 47percent. Another pathway (Strategy B) substituted bromo-Alkyl-phthalimides using NaN3 as the nucleophile, sequential CuAAC and deprotection of phthalimide group with hydrazine producing amino-Triazoles. The subsequent reaction with 1,4-NQ produced 2-Amino-Alkyl-1,2,3-Triazole-1,4-NQ derivatives in an overall yield of 45-76percent in four steps. After we developed these two strategies, linear synthesis (Strategy A) was chosen to prepare 2-[(2-(1H-1,2,3-Triazol-1-yl)ethylamino)]-3-(3-methylpropenyl)-1,4-naphthoquinones from lawsone with an overall yield of approximately 27percent in six steps. On the other hand, convergent synthesis (Strategy B) was employed for the synthesis of 2-[(4-phenyl-1H-1,2,3-Triazol-1-yl)alkyl-Amino)]-3-(3-methylbut-2-en-1-yl)-1,4-naphthoquinones from the reaction between 2-methoxy-lapachol with amino-Triazoles with a global yield of about 21percent. These synthetic strategies might lead us to new opportunities to build small-molecule libraries for future biological exploration.

Synthesis, characterization and catalytic activity of novel ruthenium complexes bearing NNN click based ligands

Novel air stable ruthenium(ii) complexes bearing tridentate ligands bis((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine (L1), 1-(1-benzyl-1H-1,2,3-triazol-4-yl)-N-(pyridin-2-ylmethyl)methanamine (L2) or 2-(4-phenyl-1H-1,2,3-triazol-1-yl)-N-(pyridin-2-ylmethyl)ethan-1-amine (L3) were synthesised. The nitrogen based ligands were easily prepared by virtue of click chemistry using cheap and commercially available reagents. The ruthenium complexes were obtained by heating the Ru(PPh3)3Cl2 precursor and the tridentate NNN ligand in toluene under reflux for 2 hours, achieving yields of 82-87%. These complexes were fully characterized by means of NMR, FT-IR and high resolution ESI spectroscopy. The crystal structure of one of the complexes was determined. These complexes showed excellent activity and selectivity in the hydrogenation of ketones and aldehydes. DFT calculations show that complex 3 may react through an outer-sphere catalytic cycle rather than via an inner-sphere mechanism.

Aminotriazole Mn(I) Complexes as Effective Catalysts for Transfer Hydrogenation of Ketones

A catalytic system based on complexes comprising abundant and cheap manganese together with readily available aminotriazole ligands is reported. The new Mn(I) complexes are catalytically competent in transfer hydrogenation of ketones with 2-propanol as hydrogen source. The reaction proceeds under mild conditions at 80 °C for 20 h with 3 % of catalyst loading using either KOtBu or NaOH as base. Good to excellent yields were obtained for a wide substrate scope with broad functional group tolerance. The obtained results by varying the substitution pattern of the ligand are consistent with an out-sphere mechanism for the H-transfer.

Phase transfer agent assisted biphasic CuAAC reaction

A phase transfer agent assisted biphasic Cu(i) catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) reaction system was developed. A biphasic reaction medium consisting of water and an organic solvent ensures the dissolution of reagents and substrates

N-(Propargyl)diazenecarboxamides for 'click' conjugation and their 1,3-dipolar cycloadditions with azidoalkylamines in the presence of Cu(II)

Propargyl functionalized diazenes 1 were prepared by two different approaches and were examined as alkyne click components in copper-catalyzed azide-alkyne cycloadditions (CuAAC) with 2-(azidomethyl)pyridine 5a and four α-azido-ω-aminoalkanes C2-C5 (5b-e)