Synthesis of coumarin–nucleoside conjugates via Huisgen 1,3-dipolar cycloaddition

Design and synthesis of antimicrobial, anticoagulant, and anticholinesterase hybrid molecules from 4-methylumbelliferone

“…Indeed, in our investigation, dimethylformamide was found to be an excellent solvent for the reaction of allyl and propargylbromide with 4-methylumbelliferone 1, in the presence of NaH. The dipolarophiles 2 and 3 were obtained in 75% and 65% yield, respectively and which were identified by the spectroscopic means ( 1 H, 13 C, and ES-HRMS) 43,35 . In recent years, the click chemistry is a powerful tool, allowing synthetic chemists to obtain selectivity, simple experimental setup, tolerance to various functional groups and quantitative yields 36 .…”

An Efficient Synthesis of Mono and Bis‐1,2,3‐triazole AZT Derivatives via Copper(I)‐catalyzed Cycloaddition

“…IR spectra were recorded on a Shimadazuir-408. 1 H, 13 C NMR spectra were recorded on a Bruker Avance 400 MHz spectrometer operating at 400.13 and 100.61 MHz, respectively, with 13 C spectra being recorded as proton-decoupled. NMR spectra were recorded in DMSO or CDCl 3 at room temperature (20 ± 3°C).…”

“…Cu(I)-catalyzed 1,3-dipolar cycloaddition is premiere example of a click chemistry employed in a wide range of applications within drug discovery, including modification of cell surfaces, specific labeling of virus particles, proteins, oligonucleotides and synthesis of new glycoproteins and dendrimers. 13 Generation of the 1,2,3-triazoles moiety in the 3¢-position of 2¢-deoxyribose nucleosides through the 1,3-dipolar cycloaddition of organic azides with alkynes has been * Corresponding author. Tel: +86-371-67767051; Fax: +86-371-67767051; E-mail: chenxl@zzu.edu.cn reported by Wigerinck P.'s and Tourirte M.'s groups.…”

meso-Phenyl-triazole bridged porphyrin-coumarin dyads: Synthesis, characterization and photophysical properties

“…The propargyloxycoumarins (8a-e) were synthesized from 7-hydroxycoumarins (4a-d; 0.56 mmol) or 4-hydroxycoumarin (4e; 0.56 mmol) and propargylbromide (0.84 mmol) by following the literature procedure and characterized on the basis of spectral data [44,45]. The characterization data of compounds (8c-d) are presented below.…”

“…Further, these molecules underwent Sonogashira coupling with trimethylsilylacetylene in the presence of PdCl 2 (PPh 3 ) 2 and Et 3 N in DMF at 90 °C to afford trimethylsilyl protected coumarinoalkynes (6a-c) which on deprotection in the presence of K 2 CO 3 in methanol provided desired 7-ethynylcoumarins (7a-c) in 78-81% yields. Also, the coumarinoalkynes (8a-e) were prepared in good yields by the reaction of compounds (4a-e) with propargyl bromide in acetone containing K 2 CO 3 at 50 °C according to the literature procedure [44].…”