62072-18-8

Upstream product

• 1572-10-7 3⁽⁵⁾-phenylpyrazol-5⁽³⁾-amine 
• 827-41-8 3-phenylpyrazol-5-amine 
• 60270-00-0 5-phenyl-3-pyrazolediazonium chloride 

Downstream Products

• 111005-20-0 2-phenyl-6,7,8,9-tetrahydropyrazolo<5,1-c><1,2,4>triazine 
• 132501-79-2 1,4-dihydro-4,4-dimethoxy-7-phenylpyrazolo<5,1-c><1,2,4>triazine 
• 66612-81-5 4,7-diphenyl-pyrazolo[5,1-c][1,2,4]triazine 
• 132501-80-5 4-methoxy-7-phenylpyrazolo<5,1-c><1,2,4>triazine 
• 1448041-54-0 ethyl [(4Z)-7-phenylpyrazolo[5,1-d][1,2,3,5]thiatriazin-4-ylidene]carbamate 
• 1448041-55-1 (Z)-N-(7-phenyl-4H-pyrazolo[5,1-d][1,2,3,5]thiatriazin-4-ylidene)benzamide 
• 1448041-56-2 (Z)-2,3,4,5-tetrafluoro-N-(7-phenyl-4H-pyrazolo[5,1-d][1,2,3,5]thiatriazin-4-ylidene)benzamide 
• 73997-08-7 3,7-Diphenyl-pyrazolo<5,1-d>-1,2,3,5-tetrazin-4(3H)-on 

Relevant academic research and scientific papers

Synthesis and properties of 5-aryl-3-diazo-3H-pyrazoles and 3-aryl-1H-pyrazole-5-diazonium salts. Preparation and cytolytic activity studies of 2-arylpyrazolo-[5,1-c][1,2,4]benzotriazines

[Figure not available: see fulltext.] A comparative analysis of physicochemical properties and reactivity of 3-aryl-1H-pyrazole-5-diazonium tetrafluoroborates and 5-aryl-3-diazo-3H-pyrazoles in azo coupling reactions is presented. It is shown that diazonium salts have higher reactivity compared to the respective 3-diazopyrazoles, which is in agreement with their physicochemical properties. Heterocyclization of the synthesized azo compounds provided 2-arylpyrazolo[5,1-c][1,2,4]benzotriazines, which were screened for antitumor activity against human uterine endothelium cancer cells (HeLa cell line) and human skin fibroblasts using the MTT assay and flow cytometry. It was found that all of the tested compounds exhibited moderate to high cytotoxic activity. The best results were obtained with 6,8-dimethoxy-2-phenylpyrazolo-[5,1-c][1,2,4]benzotriazine.

Synthesis of new azolo[5,1-d][1,2,3,5]tetrazin-4-ones–analogs of antitumor agent temozolomide

Reactivity of 5-diazoimidazoles and 5-diazopyrazoles in the reactions with alkyland aryl isocyanates was studied. A number of new imidazo-and pyrazolo[5,1-d][1,2,3,5]tetrazin-4 ones were synthesized, which are analogs of temozolomide. It was shown that diazoazoles do not react with isothiocyanates under similar conditions.

Synthesis and structure of new imidazo- and pyrazolo[5,1-d][1,2,3,5] thiatriazines based on the reaction of diazoazoles with acyl isothiocyanates controlled by Sa?O interaction

5-Diazoimidazoles and 5-diazopyrazoles have been shown to react with acyl isothiocyanates yielding the imidazo- and pyrazolo[5,1-d][1,2,3,5]thiatriazines stabilized by a nonbonded Sa?O interaction. In contrast to acyl isothiocyanates, alkyl-, aryl-, and arylsulfonyl isothiocyanates do not react with 5-diazoazoles. The nature and the strength of stabilizing intramolecular interaction between non-bonded S and O atoms have been studied by X-ray analysis for mono crystals and DFT calculations for selected azolo[5,1-d][1,2,3,5] thiatriazines. The interaction was described in terms of Weinhold covalence ratio factors, NBO, and AIM schemes. The reaction discovered was used to develop an efficient approach toward the new 8-substituted 4-ethoxycarbonylimino-4- benzoyl- and 4-(3,4,5,6-tetrafluorobenzoyl)iminoimidazo(pyrazolo)[5,1-d][1,2,3, 5]thiatriazines.

Reactivity of Diazoazoles with Electron-rich Double Bonds

The energies of several intermediates that could arise from the reaction of diazoazoles with alkenes have been estimated by means of the MNDO and AM1 SCF-MO methods as well as, in some cases, by means of ab initio methods, at the 3-21G level.All the nine

Dipolar Cycloaddition Reactions of Diazoazoles with Electron-Rich and with Strained Unsaturated Compounds

Regiospecific net 1,7-cycloaddition reactions of electron-rich or strained olefins and electron-donor acetylenes occur readily (-70 to -10 degC) with diazoazoles having nitrogen in the 2-positions of their azole rings.Diazoazoles such as 5-tert-butyl-3-diazo-3H-pyrazole (20), 3-diazo-5-phenyl-3H-pyrazole (24), 2-diazo-2H-imidazole (28), 4,5-dicyano-2-diazo-2H-imidazole (12), 4-diazo-4H-imidazole (63), 4-diazo-5-phenyl-4H-1,2,3-triazole (70), 5-cyano-4-diazo-4H-1,2,3-triazole (74), 3-diazo-3H-1,2,4-triazole (76), and 3-diazo-5-phenyl-3H-1,2,4-triazole (79) thus usually add effectively to unsaturated reactans such as enamines, 1-alkoxyalkenes, ketene acetals, aryl isocyanates, norbornene, and norbornadiene to give new 1,7-cycloadducts.These cyclization reactions may be followed by tautomerization processes leading to new stabilized fused heterocycles or by elimination to novel highly delocalized heteroaromatic derivatives. 4,5-Dicyano-2-diazo-2H-imidazole (12) undergoes various accelerated cycloadditions to unsaturates and adds to norbornene and norbornadiene by exclusive exo dipolar processes.Addition of activated acetylenes to representative α-diazoazoles also results in regiospecific 1,7-cyclization to give stabilized fused azolo heterocycles.

Reactions with Diazoazoles, VII. 3H-Azolo-1,2,4-triazoles by 1,8- or 1,12-Electrocyclizations of 3H-Pyrazol-3-one- or 3H-Indazol-3-one (Diorganylmethylene)hydrazones, Respectively

3H-Azolo-1,2,4-triazoles 3 are formed by cycloreactions of diazoazoles 1 with diazoalkanes 2 and with fluorene-N-,P-,S-ylides 4, respectively, (Method A) or by cyclizing dehydrogenation of diorganylmethanone (1H-azol-3-yl)hydrazones 7 (Method B).In both m

Reactions with Diazoazoles. Part IV. (1). - and -Cyclocondensation Reactions of Diazoazoles with Acyltriphenylphosphonium Methylides to Azolotriazines

Acyltriphenylphosphoniummethylides react with diazoazoles in a - or -cycloaddition reaction followed by elimination of triphenylphosphane oxide to yield azolotriazines.