39735-76-7

Upstream product

• 540-38-5 p-Iodophenol 
• 106-96-7 propargyl bromide 
• 13610-02-1 1-phenoxy-2-propyne 
• 107-19-7 propargyl alcohol 

Downstream Products

• 30312-03-9 1,6-bis(4-iodophenoxy)-2,4-hexadiyne 
• 540-38-5 p-Iodophenol 
• 1170318-72-5 tert-butyl 4-(2-(2-(2-(4-((4-iodophenoxy)methyl)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethoxy)phenylcarbamate 
• 1219002-52-4 C₄₀H₄₆IN₅O₆Si 
• 1443426-96-7 C₃₃H₅₅IN₂₄O₁₃Si₈ 

Relevant academic research and scientific papers

Fluorescent Probes from Stable Aromatic Nitrile Oxides

Stable aromatic nitrile oxides underwent a 1,3-dipolar cycloaddition reaction with 1-iodo-4-(prop-2-yn-1-yloxy)benzene to afford the expected isoxazoles in very good yields as single regioisomers. The formation of the 5-substituted isoxazoles is in agreement with frontier orbital theory. The reductive cleavage of the N–O bond followed by complexation with BF3·Et2O afforded the corresponding boron complexes, which were further derivatized with a triple bond for click chemistry applications. The photochemical behavior and the fluorescence properties of the derivatives were investigated and discussed, taking theoretical calculations into consideration.

Water-Tolerant ortho-Acylation of Phenols

A metal-free, water-tolerant, and one-pot process for ortho-acylation of phenols promoted by the iodine source/hydrogen peroxide system has been developed. This transformation undergoes ether formation, iodocyclization, C-C bond cleavage, and oxidative hydrolysis in a one-step manner, which is supported by control experiments.

Synthesis, characterization, and antiplasmodial efficacy of sulfonamide-appended [1,2,3]-triazoles

A series of benzenesulfonamide-appended [1,2,3]-triazole hybrids was synthesized by using [3 + 2] cycloaddition of primary, secondary, and tertiary sulfonamide azides with various phenoxymethylacetylenes under click reaction conditions. After structural c

Iron-Mediated Cyclization of 1,3-Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene-Fused Chromenes

The synthesis of selenophene-fused chromene derivatives starting from 1,3-diynyl propargyl aryl ethers is reported herein. The method is based on carbon-carbon, carbon-selenium, selenium-carbon and carbon-selenium bonds formation in a one-pot protocol, using iron(III) chloride and dibutyl diselenide as promoters. The same reaction conditions were applied to propargyl anilines leading to the formation of 1-(butylselanyl)-selenophene quinolines. The results showed that the dilution and temperature of substrate addition had a crucial influence in the products obtained. When the substrates were added at room temperature, in the absence of a solvent, a mixture of products was obtained, whereas the slowly addition (15 min) of starting materials, as a dichloromethane solution, at 0 °C led to the product formation in good yields. The mechanistic study indicates that the cooperative action between iron(III) chloride and dibutyl diselenide was essential to promote the cyclization, whereas separately none of them was effective in promoting the cyclization. We proved the synthetic utility of heterocycles obtained in the Suzuki cross coupling reaction, giving the corresponding cross-coupled products in good yields. In addition, the organoselenium moiety was removed from the structures of products by using n-butyllithium. (Figure presented.).

Ag-NHC anchored on silica: An efficient ultra-low loading catalyst for regioselective 1,2,3-triazole synthesis

A silica-supported silver complex, Ag-NHC@SiO2, was prepared by an anchoring coordination technique, which was successfully employed for the click reaction under mild reaction conditions. The protocol offered the remarkable advantages of operat

Photocatalytic Oxidative Iodination of Electron-Rich Arenes

A visible-light-mediated oxidative iodination of electron-rich arenes has been developed. 2.5 mol% of unsubstituted anthraquinone as photocatalyst were used in combination with elementary iodine, trifluoroacetic acid and oxygen as the terminal oxidant. The iodination proceeds upon irradiation in non- or weakly-electron donating solvents (DCM, DCE and benzene) wherein a spectral window in strongly coloured iodine solutions can be observed at around 400 nm. The method provides good to excellent yields (up to 98%) and shows excellent regioselectivity and good functional group tolerance (triple bonds, ketone, ester, amide). Moreover, the photo-iodination was also upscaled to a 5 mmol scale (1.1 g). Mechanistic investigations by intermediate trapping and competition experiments indicate a photocatalytic arene oxidation and the subsequent reaction with iodine as a likely mechanistic pathway. (Figure presented.).

Design and synthesis of 1,2,3-triazole-etodolac hybrids as potent anticancer molecules

A series of novel 1,2,3-triazole-etodolac hybrids (6a-l) were designed and synthesized as potent anti-cancer molecules. The synthesis strongly relied on Huisgen's 1,3-dipolar cycloaddition between etodolac azide 3 and substituted terminal alkynes 5a-l. Th

Synthesis and antibacterial evaluation of novel sulfonamide based [1,2,3]-triazoles

A new series of sulfonamide based [1,2,3]-triazoles 4a-i, 5 and 6 has been prepared in 65-99% yield through Huisgen [3+2] cycloaddition reaction of 4-azido-N-substitutedbenzenesulfonamides 2a,b with various alkynes (3a-i or phenyl acetylene) in the presence of CuSO4.5H2O and sodium ascorbate in t-butanol and water (1:1) mixture at 40°C. The structures of all the newly synthesized molecules have been established on the basis of IR, 1H and 13C NMR and high resolution mass spectral analysis. Furthermore, these compounds have been evaluated for their preliminary in vitro antibacterial activity against two Gram-negative bacteria viz. Escherichia coli (MTCC 433) and Salmonella enterica ser. typhi (MTCC 733) and a Gram-positive bacterium viz. Streptococcus mutans (MTCC 497) by using MTT assay.

Synthesis of Potential Bioactive Novel 7-[2-Hydroxy-3-(1,2,3-triazol-1-yl) propyloxy]-3-alkyl-4-methylcoumarins

A series of 50 novel 7-[2-hydroxy-3-(1,2,3-triazol-1-yl)propyloxy]-3-alkyl-4-methylcoumarins had been designed and synthesized in good to excellent yields via Cu(I)-catalyzed 1,3-dipolar cycloaddition reaction "click chemistry" of 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarins with variety of acetylene derivatives. In turn, the precursor compound, that is, 7-(3-azido-2-hydroxypropyloxy)-3-alkyl-4-methylcoumarin, was synthesized by condensation of epichlorohydrin with 7-hydroxy-3-alkyl-4-methylcoumarins followed by opening of the epoxide ring in the resulted 7-epoxymethoxy-3-alkyl-4-methylcoumarins with sodium azide. All the synthesized compounds were unambiguously identified on the basis of their spectral data analyses (IR, 1H-NMR, 13C-NMR spectra, and HRMS).

Cu(I)-catalyzed efficient synthesis of 2'-triazolo-nucleoside conjugates

A small library of thirty-two 2'-triazolyl uridine and 2'-triazolyl-5-methyluridine has been synthesized by Cu(I)-catalyzed condensation of 2'-azido-2'-deoxyuridine and 2'-azido-2'-deoxy-5-methyluridine with different alkynes and aryl propargyl ethers in almost quantitative yields. Triazolo-nucleoside conjugates, which can be evaluated for different biological activity for suitable drug development, were unambiguously identified on the basis of 1H NMR, 13C NMR, IR, and HRMS data analysis. These compounds have been synthesized for the first time and have not been reported in the literature earlier.