10316-56-0

Upstream product

• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 120-12-7 anthracene 
• 15988-11-1 4-Phenylurazole 
• 13715-59-8 9,10-dimethyl-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 
• 1330068-46-6 C₂₈H₂₇N₃O₂ 

Downstream Products

• 70332-89-7 2-phenyl-hexahydro-6,9-cyclo-[1,2,4]triazolo[1,2-a]indazole-1,3-dione 
• 70332-87-5 9-phenyl-6,6a,12,12a-tetrahydro-5H-5,12-cyclo-benzo[e][1,2,4]triazolo[1,2-a]indazole-8,10-dione 
• 96227-96-2 8-oxo-N-phenyl-4,5-diazatricyclo<4.3.0.0^3,7>nonane-4,5-dicarboxamide 
• 79769-96-3 C₁₆H₁₅N₃O₂ 
• 79770-00-6 C₁₆H₁₅N₃O₂ 
• 79769-98-5 C₁₆H₁₅N₃O₂ 
• 70332-90-0 9-phenyl-6,6a,12,12a-tetrahydro-5H-6,12-methano-benzo[e][1,2,4]triazolo[1,2-a]indazole-8,10-dione 
• 13715-59-8 9,10-dimethyl-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 
• 1330068-60-4 C₂₃H₁₇N₃O₂ 
• 1330068-44-4 C₃₄H₂₃N₃O₂ 
• 1330068-62-6 C₂₂H₁₃Cl₂N₃O₂ 
• 1330068-65-9 C₂₆H₂₃N₃O₄ 
• 13715-61-2 9,10-diethoxy-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 
• 1330068-46-6 C₂₈H₂₇N₃O₂ 

Relevant academic research and scientific papers

Reactivity Variation of Tetracyanoethylene and 4-Phenyl-1,2,4-Triazoline-3,5-Dione in Cycloaddition Reactions in Solutions

The reasons for the very high reactivity and variability of reactivity of two dienophiles, tetracyanoethylene (1) and 4-phenyl-1,2,4-triazoline-3,5-dione (2), in the Diels–Alder reactions were considered. The data on the rate of reactions with anthracene (3), benzanthracene (4) and dibenzanthracene (5) in 14 solvents over a range of temperatures and high pressures, data on the change in the enthalpy of solvation of reagents, transition state, and adducts in the forward and backward reactions, and the enthalpies of these reactions in solution were obtained. Strong π-acceptor dienophile 1 has sharply reduced reactivity in reactions in π-donor aromatic solvents. It was observed that the π-acceptor properties of dienophile 1 disappear upon passage to the transition state and adduct. Large solvent effects on the reaction rate can be predicted for all types of reactions involving tetracyanoethylene. Very high reactivity of dienophiles 1 and, especially, 2 can be useful to catch such carcinogenic impurities such as 3–5 and neutralize them by transformation into less dangerous adducts.

Reactivity of 4-Phenyl-1,2,4-triazoline-3,5-dione and Diethylazocarboxylate in [4+2]-Cycloaddition and Ene Reactions: Solvent, Temperature, and High-Pressure Influence on the Reaction Rate

We have studied the solvent, temperature, and pressure influences on the reaction rates of cyclic and acyclic N=N bonds in the Diels-Alder and ene reactions. The transfer from N-phenylmaleimide (9) to a structural analogue, 4-phenyl-1,2,4-triazoline-3,5-dione (2), is accompanied by the rate increase in five to six orders of magnitude in the Diels-Alder reactions with cyclopentadiene (4) and 9,10-dimethylanthracene (5), whereas the transfer from dimethyl fumarate (10) to diethyl azodicarboxylate (1) increases only in one to two orders of magnitude. The ratio of the reaction rate constants (2 + 4)/(1 + 4) is very large (5.2 × 107) and almost the same (5.3 × 107) as in the ene reactions with tetramethylethylene (7), (2 + 7)/(1 + 7). It has been observed that the N=N bond in reagent 2 has strong electrophilic, and its N-N moiety in the transition state has nucleophilic properties, which results from the analysis of the solvation enthalpy transfer of reagents, activated complex, and adduct in the Diels-Alder reaction of 2 with anthracene 22.

Diels-Alder reaction rate in the solid state and the evidence of the location of molecular complexes between the reagents on the reaction pathway

The rate of reactions in the solid phase with uniform grinding of crystals of dienes, anthracene, and 9,10-dimethylanthracene, with dienophiles, tetracyanoethylene, N-phenylmaleimide, and 4-phenyl-1,2,4-triazoline-3,5-dione, has been studied. It was shown

Features of the Diels-Alder reaction between 9,10-diphenylanthracene and 4-phenyl-1,2,4-triazoline-3,5-dione

The Diels-Alder reaction between substituted anthracenes 1a-1j and 4-phenyl-1,2,4-triazoline-3,5 (2) is studied. In all cases except one, the reaction proceeds on the most active 9,10-atoms of substituted anthracenes. The orthogonality of the two phenyl groups at the 9,10-position of diene 1a is found to shield 9,10-reactive centers. No dienophiles with C=C bonds are shown to participate in the Diels-Alder reaction with 1a; however, the reaction 1a + 2 proceeds with the very active dienophile 2,4-phenyl-1,2,4-triazoline-3,5-dione. It is shown that attachment occurs on the less active but sterically accessible 1,4-reactive center of diene 1a. The structure of adduct 3a is proved by 1H and 13C NMR spectroscopy and X-ray diffraction analysis. The following parameters are obtained for reaction 1a + 2 ? 3a in toluene at 25°C: Keq = 2120 M-1, ΔHf≠ = 58.6 kJ/mol, ΔSf≠ = -97 J/(mol K), ΔVf≠ = -17.2 cm3/mol, ΔHb ≠ = 108.8 kJ/mol, ΔSb≠ = 7.3 J/(mol K), ΔVb≠ = -0.8 cm3/mol, ΔHr-n = -50.2 kJ/mol, ΔSr-n = -104.3 J/(mol K), ΔVr-n = -15.6 cm3/mol. It is concluded that the values of equilibrium constants of the reactions 1a-1j + 2 ? 3a-3j vary within 4 × 101-1011 M-1.

Homo-Diels-Alder reaction of a very inactive diene, bicyclo[2,2,1]hepta-2, 5-diene, with the most active dienophile, 4-phenyl-1,2,4-triazolin-3,5-dione. Solvent, temperature, and high pressure influence on the reaction rate

Solvent, temperature, and high pressure influence on the rate constant of homo-Diels-Alder cycloaddition reactions of the very active hetero-dienophile, 4-phenyl-1,2,4-triazolin-3,5-dione (1), with the very inactive unconjugated diene, bicyclo[2,2,1]hepta

A convenient methodology for the in situ oxidation of 4-substituted urazoles. Setting UP a one-pot procedure for the efficient protection of dienes

The oxidation of 4-substituted urazoles to the corresponding 1,2,4-triazoline-3,5-diones can be performed selectively in the presence of dienic systems by the action of the nitrosonium ion, formed in situ by stoichiometric amounts of sodium nitrite and ac

Dynamic Covalent chemistry: A facile room-temperature, reversible, diels-alder reaction between anthracene derivatives and n-phenyltriazolinedione

A series of readily accessible, dynamic Diels-Alder reactions that are reversible at room temperature have been developed between anthracene derivatives as dienes and N-phenyl-1,2,4-triazoline-3,5-dione as the dienophile. The adducts formed undergo reversible component exchange to form dynamic libraries of equilibrating cycloadducts. Furthermore, reversible adduct formation allows temperature-dependent modulation of the fluorescent properties of anthracene components; a feature of potential interest for the design of optodynamic polymeric materials by careful selection and manipulation of these simple dienes and dienophiles. Copyright

Synthesis of Urazoles via Cycloaddition Employing 4-Phenyl-4H-1,2,4-Triazole-3,5-dione (PTAD) Transfer

A new method was developed involving transfer of 4-phenyl-4H-1,2,4-triazole-3,5-dione (PTAD) from thermally labile urazoles 9 and 10 to bicyclic olefin derivatives 1-8, which irreversibly undergo cycloaddition accompanied by Wagner-Meerwein rearrangement.In most cases purer products and significantly improved yields of the corresponding urazoles 11-18 are obtained than by direct PTAD cycloaddition.