Refernces
10.1007/s00706-007-0649-7
The research focuses on the synthesis of novel heterocyclic compounds, specifically 1,2,4-triazol-3-ylmethyl-, 1,3,4-oxa-, and -thiadiazol-2-ylmethyl-1H-[1,2,3]-triazolo[4,5-d]pyrimidinediones, which are potentially useful as antiviral agents against hepatitis B virus. The experiments involved the synthesis of 1-carbethoxymethyl-4,6-dimethyl-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione and its subsequent reactions with hydrazine hydrate to yield a hydrazide. This hydrazide was further reacted with phenylisothiocyanate or carbon disulfide and KOH to produce thiosemicarbazide and oxadiazole derivatives. Various alkylation and cyclization reactions were performed to form the desired heterocyclic structures, including the formation of 1,3,4-thiadiazole, 5-mercapto-1,2,4-triazole, and 1,3,4-oxadiazole rings. The synthesized compounds were analyzed using techniques such as infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS) to confirm their structures. The reactants used in these syntheses included phenylisothiocyanate, carbon disulfide, alcoholic potassium hydroxide, dimethyl sulfate, ethyl chloroacetate, and various monosaccharide aldoses. The synthesized compounds were tested for their antiviral activity, with some showing moderate activities against hepatitis B virus.
10.1007/s10562-014-1288-3
The research investigates a novel catalytic system for the one-pot synthesis of 2,5-disubstituted-1,3,4-oxadiazoles using cetyltrimethylammonium bisulphate ([CTA]HSO4) generated in situ from cetyltrimethylammonium peroxodisulphate (CTAPS) in a choline chloride–urea deep eutectic solvent (DES). The purpose is to develop an efficient, environmentally friendly, and cost-effective method for synthesizing 1,3,4-oxadiazoles, which are important heterocycles used in various fields such as medicines, pesticides, and dyes. The study concludes that this method offers several advantages over traditional procedures, including milder reaction conditions, simplicity in workup and purification, good to excellent yields, and the use of inexpensive, recyclable reagents.
10.1246/bcsj.79.644
This research aims to synthesize and characterize a series of 1,3,4-oxadiazole–1,2,3-triazole hybrid derivatives as potential blue electroluminescent materials. The study introduces 1,2,3-triazole into the skeletal structure of 1,3,4-oxadiazole to create these hybrid compounds. Key chemicals used in the synthesis include POCl3, DMF, ethyl 4-hydrazinylbenzoate, benzoyl chloride, and various substituted benzohydrazides. The UV–vis absorption maxima of these derivatives are in the range of 340–360 nm, and their photoluminescence maxima are between 406–480 nm. The fluorescence quantum yields range from 0.65 to 0.76. Cyclic voltammetry measurements reveal unclearly reversible reduction processes, with HOMO values and bandgap energies indicating their potential as electron-transporting materials. The study concludes that the 1,3,4-oxadiazole–1,2,3-triazole derivatives are highly potential efficient blue electroluminescent materials, with the triazole moiety playing a significant role in controlling fundamental photolytic processes.
10.1039/b616996a
The study investigates the optical properties of 1,3,4-oxadiazole-containing molecules and their design principles to improve efficiency for organic optoelectronics. Researchers synthesized a series of oxadiazole compounds and ethynylene analogs to systematically compare their optical behaviors. The 1,3,4-oxadiazole moiety, known for enhancing charge balance and stability in optoelectronic materials, was found to be optically transparent in the visible range and fully conjugating, similar to ethynylene units. However, para-dialkoxy substituents adjacent to the oxadiazole rings were discovered to cause a significant drop in quantum yield due to a repulsive interaction that hinders excited-state planarity and promotes non-radiative decay. The study provides design principles to prevent this quantum yield reduction, such as using single alkoxys or para-alkyls instead of para-dialkoxy substituents, which helps maintain high quantum efficiency while enhancing solubility.
10.1055/s-0034-1380493
The research aimed to develop an efficient and environmentally benign method for the synthesis of 1,3,4-oxadiazoles, which are important heterocyclic compounds with a broad spectrum of biological activities and applications in medicinal chemistry. The study focused on the photoredox-catalyzed oxidative heterocyclization of semicarbazones using eosin Y as a visible-light photocatalyst and carbon tetrabromide (CBr4) as a bromine source. The process involved the irradiation of the reaction mixture with green LEDs under atmospheric oxygen, leading to the formation of 5-substituted 2-amino-1,3,4-oxadiazoles in high yields (86–96%) within 10–14 hours. The researchers concluded that this method offered a rapid, mild, and operationally simple approach to synthesize valuable 1,3,4-oxadiazoles, utilizing visible light and atmospheric oxygen, and was superior to traditional methods that often required harsh conditions and multistep processes.