13274-44-7

Upstream product

• 13482-67-2 ethyl 2-((4-methoxyphenyl)carbamoyl)hydrazinecarboxylate 
• 13274-46-9 4-(4-methoxyphenyl)urazole 

Downstream Products

• 1258974-70-7 C₃₁H₄₁N₃O₅Si 
• 1354201-91-4 C₂₃H₂₃N₃O₆ 
• 1258974-36-5 C₂₂H₂₁N₃O₅ 
• 119020-68-7 3-(4-methoxyphenyl)-6-ethoxycarbonyl-1,3,5-triazabicyclo[3.1.0]hexane-2,4-dione 

Relevant academic research and scientific papers

Supported nitric acid on silica gel and polyvinyl pyrrolidone (PVP) as an efficient oxidizing agent for the oxidation of urazoles and bis-urazoles

A method for the oxidation of a good range of urazoles and bis-urazoles to the corresponding triazolinediones by supported nitric acid on silica gel (SiO2-HNO3) and/or polyvinyl pyrrolidone (PVP-HNO3) is described. Reactions have been carried out heterogeneously at room temperature in dichloromethane with good to excellent yields.

Catalytic oxidation of urazoles and bis-urazoles to their corresponding triazolinediones using aluminium nitrate and a catalytic amount of silica sulfuric acid

A simple and efficient catalytic oxidation of urazoles and a bis-urazole to the corresponding triazolinediones by treatment with Al(NO3) 3.9H2O in the presence of a catalytic amount of silica sulfuric acid is described. A good range of urazole derivatives was selectively oxidized in CH2Cl2 at room temperature in good to excellent yields.

Oxidative ring cleavage of 4-(4-R-phenyl)-1,2,4-triazolidine-3,5-diones: Electrochemical behavior and kinetic study

Cyclic voltammetry results as a diagnostic technique for electrochemical oxidation of 4-(4-R-phenyl)-1,2,4-triazolidine-3,5-diones (1-5) are reported and discussed. The results indicate that the electrochemically generated 4-(4-R-phenyl)-4H-1,2,4-triazole-3,5-diones (1ox-5ox) are unstable and participate in oxidative ring cleavage. In this study, the effect of different parameters such as pH, 4-phenylurazole concentration, solvent, temperature, substitute effect and time window of chosen electrochemical method have been studied. Also, the transfer coefficient, α, exchange current density, J0, the formal potential, E0′ and diffusion coefficient, D, of 4-phenylurazole (1) have been calculated. In addition, the observed homogeneous rate constants of oxidative ring cleavage of 4-phenylurazole derivatives were estimated by comparing the experimental cyclic voltammetric responses with digital simulated results.

Proton, Electron, and Hydrogen Atom Transfers from Ions, Radical, and Radical Ions Derived from Substituted Urazoles and Triazolediones

In dimethyl sulfoxide (DMSO) solution, pKa's for the monoanion and radical derived from 4-phenylurazole have been determined to be 24.8 and 9 +/- 2, respectively.The acidity constant for the 4-phenylurazolyl radical has been determined via a thermochemical cycle that incorporates proton- and electron-transfer data for ions and radicals derived from 4-phenylurazole and 4-phenyl-1,2,4-triazoline-3,5-dione.The acidity data indicate that (a) the 4-phenylurazolide monoanion is ca. 14 pKa units less acidic than 4-phenylurazole (pKa = 11.0) and (b) the 4-phenylurazolyl radical is slightly more acidic than 4-phenylurazole.The estimated pKa for the 4-phenylurazolyl radical is reasonable in light of the reversible cyclic voltammetric reduction observed for 4-phenyl-1,2,4-triazoline-3,5-dione.Also in DMSO solution, the homolytic strengths of hydrazyl N-H bonds present in 4-phenylurazole as well as for the monoanion and radical derived from 4-phenylurazole, are within 3 kcal/mol of each other.These data suggest that the 4-phenylurazolyl radical disproportionation raction (forming 4-phenylurazole and 4-phenyl-1,2,4-triazoline-3,5-dione) is approximately thermoneutral.Similar relationships are found for ions, radicals, and radical ions derived from 4-methylurazole and 4-methyl-1,2,4-triazoline-3,5-dione.

Investigating Bicyclobutane-Triazolinedione Cycloadditions as a Tool for Peptide Modification

Acyl bicyclobutanes are shown to engage in strain-promoted cycloaddition reactions with a diverse array of triazolinedione reagents. The synthesis of an orthogonally protected urazole building block enabled the facile preparation of amino acid- and peptid

N2O4 chemisorbed onto n-propylsilica kryptofix 21 and kriptofix 22 as two new functional polymers for the fast oxidation of urazoles and 1,4-dihydropyridines

3-Chloropropylsilica was reacted with Kriptofix 21 or 22 in the presence of triethylamine to form N-propylsilica Kryptofix 21 and Kriptofix 22. Then N 2O4 was added to each of these polymers to chemisorb onto cavity of aza-crown ethers. These functionalized polymers were applied for the fast and simple oxidation of urazoles and 1,4-dihydropyridines, respectively.

Construction of polyheterocyclic benzopyran library with diverse core skeletons through diversity-oriented synthesis pathway: Part II

As a continuation of our previous report (J. Comb. Chem.2010, 12, 548-558), we accomplished the diversity-oriented synthesis of polyheterocyclic small-molecule library with privileged benzopyran substructure. To ensure the synthetic efficiency, we utilized the solid-phase parallel platform and the fluorous-tag-based solution-phase parallel platform to construct a 284-member polyheterocyclic library with six distinct core skeletons with an average purity of 87% on a scale of 5-10 mg. This library was designed to maximize the skeletal diversity with discrete core skeletons in three-dimensional space and the combinatorial diversity with four different benzopyranyl starting materials and various building blocks. Together with our reported benzopyranyl library, we completed the construction of polyheterocyclic benzopyran library with 11 unique scaffolds and their molecular diversity was visualized in chemical space using principle component analysis (PCA).

Oxidation of urazoles to their corresponding triazolinediones using benzyltriphenylphosphonium nitrate

Benzyltriphenylphosphonium nitrate in the presence of AlCl3 oxidised 1,2,4-triazolidine-3,5-diones to the corresponding 4-substituted-1,2,4- triazole-3,5-diones.

Metal-Free oxidation of urazole and 1,4-dihydropyridine derivatives under mild and heterogeneous conditions by nitro urea, derived from urea nitrate, and silica sulfuric acid

Mild combination of nitro urea, derived from urea nitrate, and silica sulfuric acid (SiO2OSO3H) might act as an efficient oxidizing media, which could be able to oxidize different types of heterocyclic compounds including urazoles and 1,4-dihydropyridines. The process presented here is operationally simple, environmentally benign, and reactions have been mildly carried out in dichloromethane at room temperature.

Catalytic and efficient oxidation of urazole derivatives to their corresponding triazolinediones using ammonium nitrate and metal hydrogen sulfate as catalyst

Catalytic oxidation of a variety of urazoles to the triazolinediones via combination of NH4NO3 in the presence of a catalytic amount of aluminium hydrogen sulfate has been developed at room temperature in dichloromethane.