939-07-1

Usage

Uses

Used in Pharmaceutical Research and Development:
5-phenyl-1,2-dihydro-3H-1,2,4-triazol-3-one is used as a potential candidate for the treatment of various neurological disorders due to its pharmacological activities, including anticonvulsant, anxiolytic, and sedative properties.
Used as a Precursor in Organic Synthesis:
5-phenyl-1,2-dihydro-3H-1,2,4-triazol-3-one is used as a precursor in the synthesis of other organic compounds, contributing to the development of new chemical entities and materials.
Used in Laboratory and Industrial Settings:
5-phenyl-1,2-dihydro-3H-1,2,4-triazol-3-one is used in laboratory and industrial settings for research and development purposes, but it should be handled and used with caution due to potential hazards and health effects.

Upstream product

• 2845-79-6 1-benzoyl semicarbazide 
• 16956-44-8 N,2-dibenzoylhydrazine-1-carboxamide 
• 1612-76-6 2-amino-5-phenyl-1,3,4-oxadiazole 
• 590-28-3 potassium cyanate 
• 729-44-2 1,2-bis[chloro(phenyl)methylidene]hydrazone 
• 100-52-7 benzaldehyde 
• 7627-10-3 3-phenyl-1,2,4-oxadiazol-5-ylhydrazine 
• 1574-10-3 benzaldehyde semicarbazone 
• 28867-76-7 benzaldehyde benzylidenehydrazone 
• 124-38-9 carbon dioxide 
• 28819-30-9 benzamidrazone 
• 123-77-3 Azodicarboxamid 
• 62036-20-8 3-ethoxy-5-phenyl-1,2,4-triazole 
• 563-41-7 semicarbazide hydrochloride 

Downstream Products

• 78414-72-9 1-amino-3-phenyl-Δ²-1,2,4-triazolin-5-one 
• 291310-97-9 4-(5-oxo-4,5-dihydro-1H-[1,2,4]triazol-3-yl)-benzenesulfonyl chloride 
• 78414-73-0 1-amino-5-methoxy-3-phenyl-1,2,4-triazole 
• 78414-76-3 1-amino-4-methyl-3-phenyl-Δ²-1,2,4-triazolin-5-one 
• 78414-70-7 1-benzylideneamino-3-phenyl-Δ²-1,2,4-triazolin-5-one 
• 50369-39-6 4-methyl-3-phenyl-Δ²-1,2,4-triazolin-5-one 
• 1256844-25-3 C₁₆H₁₃N₃O₂ 
• 246848-34-0 C₁₅H₁₃N₃O₂ 
• 19081-61-9 1-(4-methylphenyl)-3-phenyl-1,2,4-triazol-5-one 
• 1256844-26-4 C₁₅H₁₀N₄O 

Relevant academic research and scientific papers

TRIAZOLONES DERIVATIVES FOR USE IN THE TREATMENT, AMELIORATION OR PREVENTION OF A VIRAL DISEASE

The present invention relates to a compound having the general formula (I), optionally in the form of a pharmaceutically acceptable salt, solvate, polymorph, prodrug, tautomer, racemate, codrug, cocrystal, enantiomer, or diastereomer or mixture thereof, which is useful in treating, ameloriating or preventing a viral disease. Furthermore, specific combination therapies are disclosed.

Design, synthesis, and biological activity of novel tetrahydropyrazolopyridone derivatives as FXa inhibitors with potent anticoagulant activity

A series of novel tetrahydropyrazolopyridone derivatives containing 1,3,4-triazole, triazolylmethyl, and partially saturated heterocyclic moieties as P2 binding element was designed, synthesized, and evaluated in vitro for anticoagulant activity in human and rabbit plasma. All compounds showed moderate to significant potency, and compounds 15b, 15c, 20b, 20c, and 22b were further examined for their inhibitory activity against human FXa in vitro. While compounds 15c and 22b were tested for rat venous thrombosis in vivo. The most promising compound 15c, with an IC50 (FXa) value of 0.14?μM and 98% inhibition rate, warranted further investigation as an FXa inhibitor.

The Base-Promoted Annulation of 2-Hydrazinyl Pyridine and CO2 toward Triazolones

A base-promoted annulation of 2-hydrazinyl pyridine and atmospheric pressure of CO2 has been developed in the presence of silane as reducing reagent, affording a series of triazolones in moderate to excellent yields. CO2 served as a carbonyl source in this transfomation. Moreover, benzamidrazones also worked well under this procedure. Thus, it represents a green, sustainable and straightforward pathway to access triazolone frameworks. (Figure presented.).

Facile access to a variety of 2,5-biaryl-1,2,4-TRIAZOL-3-ones via regioselective N-arylation of triazolones

A selective synthetic method of the 2,5-biaryltriazolones has been developed via copper-catalyzed N-arylation reaction. Aryltriazolones, which were readily prepared from commercially available compounds, were N-arylated to 2,5-biaryltriazolones with high regioselectivity. This approach allows for access to a variety of 2,5-biaryl-1,2,4-trizol-3-ones in a simple and practical manner.

Chlorosulfonation of some crisscross cycloadducts from isocyanates and diaryl azines

Reaction of chlorosulfonyl isocyanate (1) with arylaldehyde azines (7) gave the 2:1 crisscross adducts (8); attempts to prepare a disulphonamide of 8a gave only a mixture of the monosulfamide 9 and the diureide 10. The latter with trichloromethanesulfenyl chloride afforded the derivative 12a, and with chlorosulfonic acid hydrazinodicarbonamide (11). The azine 7a with benzoyl isocyanate (2) gave the expected crisscross adduct 13. With thiobenzoyl isocyanate (3) however, both 7a and 7d gave the 1:1 adducts (14), whereas 7c gave a different 2:1 adduct (15). Treatment of 14a with 1 gave the ureide 16. With both methyl isocyanate (4) and phenyl isocyanate (5), 7a gave the expected crisscross adducts (17a and b), and 7c with 5 similarly gave 17c. When 7a was treated with 1 followed by aqueous potassium iodide, the diureide (10) was formed; concentrated nitric acid converted 10 into the triazolenone (18). Treatment of 18 with chlorosulfonic acid-thionyl chloride gave the sulfonyl chloride (19) which was characterised as the sulfonamides (20 a-d). Diarylsulfamoyl azines (21 a-f) with 1 and potassium iodide, gave the diureides 22 a-f. 4-Methoxy-3-sulfamoylbenzaldehyde azines (23 a-c) reacted with 3 to give the 1:1 adducts 24 a-c, while 4-chlorosulfonylphenyl isocyanate (6) with benzaldehyde azine (7a) gave the bis-chlorosulfonyl adduct (25a), characterised as the diethylsulfonamide 25b. Attempted chlorosulfonation of the tetraphenyl cycloadduct 17b did not give the tetrasulfonyl chloride (although the reaction was successful with the more reactive methoxy adduct 17c); the tetrasulfonyl chloride (26a) was converted into 3 sulfonamides (26 b-d). The unsymmetrically-substituted diaryl azines (27) reacted with 1 and potassium iodide to yield the diureides 28 a-f. Analogous cycloadditions of 1 with several keto azines were unsuccessful. Selected compounds will be screened for medicinal and pesticidal activity: compounds 9, 10 and 12a showed fungicidal activity against barley powdery mildew.

Dihydro-1,2,4-triazin-6(1H)-ones. III oxidation products of 1-Methyl-3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one

1-Methyl-3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one (1) undergoes aerial oxidation to give a mixture of 1-methyl-3-phenyl-1,2,4-triazin-6(1H)-one (2) and 1-methyl-3-phenyl-1,4-dihydro-1,2,4-triazine-5,6-dione (3). The dehydro derivative (2) was cleanly

Photoinduced molecular rearrangements. The photochemistry of some 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles. Formation of 1,2,4-triazoles, indazoles, and benzimidazoles

The photochemistry of some 3,5-disubstituted 1,2,4-oxadiazoles in the presence of nitrogen nucleophiles [external, such as added amines or hydrazines, or internal, such as an o-aminophenyl moiety at C(3) of the oxadiazole ring] has been investigated. In the irradiation of 5-amino-(or 5-N-substituted amino) 3-phenyl-1,2,4-oxadiazoles in the presence of aliphatic primary amines (or ammonia), photolytic species arising from heterolytic cleavage of the ring O-N bond capture the nucleophilic reagent to give open-chain intermediates, which develop into 1,2,4-triazolin-5-ones. Similarly, irradiations of 3,5-diphenyl-, 3-methoxy-5-phenyl-, and 5-methyl-3-phenyl-1,2,4-oxadiazoles gave 1,2,4-triazoles. In the same context, irradiations of representative substrates in the presence of hydrazines have been also investigated. In the irradiation of 3-(o-aminophenyl)-5-methyl-, 3-[o-(methylamino)phenyl]-5-methyl-, and 3-(o-aminophenyl)-5-phenyl-1,2,4-oxadiazoles, concomitant formation of indazoles and benzimidazoles, presumably arising from a common photolytic species, has been observed. Some mechanistic aspects have been considered, and possible applications in synthesis have been pointed out.

Regeneration of Carbonyl Compounds from Semicarbazones by Copper (II) Chloride Dihydrate

Semicarbazones are chemoselectively hydrolysed to carbonyl compounds in high yields by copper (II) chloride dihydrate on refluxing in acetonitrile.

2,4-Dihydro-3H-1,2,4-triazol-3-ones as anticonvulsant agents

A series of 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones was evaluated for anticonvulsant activity. In general the members of this series were prepared by the alkaline crystalization of 1-aroyl-4-alkylsemicarbazides. The resulting 2-unsubstituted 3H-1,2,4-t

Efficient Synthesis of 5,5-Dialkyl-Δ1-1,2,4-triazolin-3-ones by Acid Hydrolysis of Bis(α-isocyanatoalkyl)diazenes

The hydrolysis of bis(α-isocyanatoalkyl)diazenes with hydrochloric acid affords the novel 5,5-dialkyl-Δ1-1,2,4-triazolin-3-ones in good yields, and as a minor by-product, the corresponding 4-aminocarbonyl derivatives.The 1,2,4-triazolin-3-ones are easily converted into the 4-benzoyl derivatives which, in turn, react as mild benzoylating agents toward primary amines.