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Journal articles on the topic 'Methylpyrazol'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Sirianni, Eric R., Glenn P. A. Yap, Eser S. Akturk, and Klaus H. Theopold. "Improved syntheses, and structural and electronic characterization of carboxamide-substituted TpCONHPh,Meand TpCONHt-Bu,Meligands." Acta Crystallographica Section C Crystal Structure Communications 69, no. 9 (2013): 947–53. http://dx.doi.org/10.1107/s0108270113015898.

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Improvements in the syntheses of the carboxamide-substituted tris(pyrazolyl)borate ligands TpCONHPh,Me[tris(3-anilinocarbonyl-5-methylpyrazol-1-yl)borate] and TpCONHt-Bu,Me[tris(3-tert-butylaminocarbonyl-5-methylpyrazol-1-yl)borate] are reported. Their TlIsalts, namely [tris(3-anilinocarbonyl-5-methylpyrazol-1-yl-κN2)borato]thallium(I), [Tl(C33H31BN9O3)], (II), and [tris(3-tert-butylaminocarbonyl-5-methylpyrazol-1-yl-κN2)borato]thallium(I), [Tl(C27H43BN9O3)], (III), as well as the CuIcarbonyl complexes (TpCONHPh,Me)Cu(CO), namely carbonyl[tris(3-anilinocarbonyl-5-methylpyrazol-1-yl-κN2)borato]

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2

Perrin, Monique, Alain Thozet, Pilar Cabildo, Rosa Ma Claramunt, Eduard Valenti, and José Elguero. "Molecular structure and tautomerism of 3,5-bis(4-methylpyrazol-1-yl)-4-methylpyrazole." Canadian Journal of Chemistry 71, no. 9 (1993): 1443–49. http://dx.doi.org/10.1139/v93-186.

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The title compound C12N6H14, 1, crystallizes in the space group P21/n (a = 8.222(2) Å, b = 27.336(8) Å, c = 5.574(2) Å, α = 90.00°, β = 100.97(4)°, γ = 90.00°), Z = 4, d = 1.308 g cm−3. The conformation about the N—C bonds linking the pyrazole rings can be defined as EZ, with "pyridine-like" nitrogen atoms in an anti disposition [Formula: see text] and "pyridine-like" and "pyrrole-like" nitrogen atoms in a syn disposition [Formula: see text] with regard to the central pyrazole. Intermolecular hydrogen bonds between the central and the terminal pyrazole ring of configuration Z form centrosymmet

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3

Fedotov, S. O., and A. S. Hotsulia. "Synthesis and properties of 3-(ethylthio)-9-methyl-6-(alkylthio)pyrazolo[1,5-d][1,2,4]triazolo[3,4-f][1,2,4]triazines." Current issues in pharmacy and medicine: science and practice 15, no. 3 (2022): 227–34. http://dx.doi.org/10.14739/2409-2932.2022.3.263994.

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The combination of pyrazole and 1,2,4-triazole fragments in one structure makes it possible to achieve some success in creating potential biologically active compounds. Various factors contribute to this process. Among them, we can note the significant possibilities of chemical transformation involving these cycles, the simplicity, and reliability of methods, the creation of molecules with a certain level of bioavailability and the ability to influence a number of biochemical processes. Taking into account the presented facts, the creation of new compounds in a number of pyrazolo-triazole cond

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4

Claramunt, R. M., C. Lopez, D. Sanz, et al. "Rhodium(I) complexes with the polydentate ligand 3,5-bis(4-methylpyrazol-1-yl)-4-methylpyrazole." Journal of Organometallic Chemistry 412, no. 1-2 (1991): 259–71. http://dx.doi.org/10.1016/0022-328x(91)86061-t.

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5

Díaz, José Luis, Jordi Corbera, Daniel Martínez, et al. "Pyrazolo[3,4-d]pyrimidines as sigma-1 receptor ligands for the treatment of pain. Part 2: Introduction of cyclic substituents in position 4." MedChemComm 8, no. 6 (2017): 1246–54. http://dx.doi.org/10.1039/c7md00078b.

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6

R., HARODE, and C. SHARMA T. "Synthesis of 2-(3'-Methylpyrazol-5-one-l'-yl)-4-arylthiazoles." Journal of Indian Chemical Society Vol. 66, Apr 1989 (1989): 282–83. https://doi.org/10.5281/zenodo.6140328.

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School of Studies in Chemistry, Vikram University, Ujjain-456 010 <em>Manuscript received 8 June 1988,  accepted 2 February 1989</em> Synthesis of 2-(3'-Methylpyrazol-5-one-I'-yl)-4-arylthiazoles

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7

Dial, Sharon M., Mary Anna Hull Thrall, and Dwayne W. Hamar. "Comparison of ethanol and 4-methylpyrazole as treatments for ethylene glycol intoxication in cats." American Journal of Veterinary Research 55, no. 12 (1994): 1771–82. http://dx.doi.org/10.2460/ajvr.1994.55.12.1771.

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Summary The efficacy of 4-methylpyrazole (4-mp) and ethanol as treatment for ethylene glycol (eg) intoxication in cats was compared. Twenty-two cats were assigned at random to 6 experimental groups. Cats of 1 experimental group were given only 4-mp; those of another experimental group were given only eg. Cats of 3 experimental groups were intoxicated with eg and given 4-mp at 0 hour or 2 or 3 hours after eg ingestion, and those of 1 experimental group were given eg and treated with ethanol 3 hours after eg ingestion. Physical, biochemical, hematologic, blood gas, serum and urine eg concentrati

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8

Fedotov, S. O., A. S. Hotsulia, and Yu V. Karpenko. "Synthesis and analgesic activity of new pyrazole-containing derivatives of 1,2,4-triazole-3-thiol." Current issues in pharmacy and medicine: science and practice 16, no. 3 (2023): 205–12. http://dx.doi.org/10.14739/2409-2932.2023.3.288364.

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Pain represents a primary symptom of numerous diseases and conditions, affecting millions of people worldwide. Effective analgesic medications can alleviate or eliminate pain, thereby enhancing patients’ quality of life and assisting them in resuming normal physical and social activities. However, several existing analgesics may carry unwanted side effects, such as ulcers, blood clotting issues, drowsiness, and more. The development of new analgesics is focused on creating drugs that are both effective and associated with fewer adverse effects. Considering the continuous rise in the number of

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9

Shi, Yao-Cheng, Bei-Bei Zhu, and Seik Weng Ng. "[1-(2-Hydroxyethyl)-5-methylpyrazol-3-yl]ferrocenium chloride and [1-(2-hydroxyethyl)-5-methylpyrazol-3-yl]ferrocene cocrystal." Acta Crystallographica Section E Structure Reports Online 63, no. 5 (2007): m1385—m1387. http://dx.doi.org/10.1107/s160053680701687x.

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10

Fedotov, S. O., and A. S. Hotsulia. "Synthesis and properties of S-derivatives of 4-amino-5-(5-methylpyrazol-3-yl)-1,2,4-triazole-3-thiol." Current issues in pharmacy and medicine: science and practice 14, no. 3 (2021): 268–74. http://dx.doi.org/10.14739/2409-2932.2021.3.243176.

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The combination of various heterocyclic systems with a wide range of properties is quite expedient and is, in practice, a justified direction for obtaining biologically active substances, which ultimately forms a favorable basis for the creation of drugs. In recent decades, the attention of scientists has been closely focused on nitrogen-containing heterocyclic compounds. Among such compounds, 1,2,4-triazole and pyrazole occupy a special place. Indeed, on the basis of these systems, a significant number of well-known drugs have been created, which are widely used at the present time. The aim o

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11

Vovk, Mykhaylo V., Andrij V. Bol'but, and Pavlo S. Lebed'. "O‐Acylation of 3‐Methylpyrazol‐5‐ones with Acylisothiocyanates." Synthetic Communications 34, no. 8 (2004): 1507–13. http://dx.doi.org/10.1081/scc-120030702.

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12

Azev, Yu A., and I. V. Teplyashina. "Reaction of dipyrazolylmethanes with 1-phenyl-3-methylpyrazol-5-one." Chemistry of Heterocyclic Compounds 34, no. 9 (1998): 1091–92. http://dx.doi.org/10.1007/bf02251560.

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13

Faure, Robert, Émile-Jean Vincent, André Rousseau, Rose Maria Claramunt, and José Elguero. "High resolution 13C nuclear magnetic resonance spectra of solid pyrazoles. Application to annular tautomerism." Canadian Journal of Chemistry 66, no. 5 (1988): 1141–46. http://dx.doi.org/10.1139/v88-187.

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Carbon-13 nuclear magnetic resonance spectroscopy in the solid state (cross polarization/magic angle spinning technique) is a very suitable method for studying the annular tautomerism of pyrazoles. In all the compounds studied, the tautomerism is frozen and the signals are well resolved except for 3,5-dimethyl-4-nitro pyrazole, which shows broad signals. In the case of 4-substituted derivatives of 3(5)-methylpyrazoles, the tautomer present in the solid state is a 4-X-5 methylpyrazole. 3-Phenyl-5-methylpyrazole (4H or 4-methyl) is favoured over the 3-methyl-5-phenyl tautomer.

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14

Attaryan, O. S., A. O. Baltayan та S. G. Matsoyan. "Synthesis of α-methyl-β-(3-methylpyrazol-1-yl)-and α-methyl-β-(5-methylpyrazol-1-yl)propionic acids and their esterification with vinyl acetate". Russian Journal of General Chemistry 77, № 2 (2007): 297–300. http://dx.doi.org/10.1134/s107036320702017x.

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15

Belmar, Julio, Fredy R. Pérez, Yanko Moreno, and Ricardo Baggio. "Two enamines derived from 1-n-alkyl-3-methylpyrazol-5-ones." Acta Crystallographica Section C Crystal Structure Communications 60, no. 9 (2004): o705—o708. http://dx.doi.org/10.1107/s0108270104018736.

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16

Sarojini, B. K., B. J. Mohan, B. Narayana, H. S. Yathirajan, Jerry P. Jasinski, and Ray J. Butcher. "(Z)-4-[2-(2,4-Dimethylphenyl)hydrazinylidene]-3-methylpyrazol-5(1H)-one." Acta Crystallographica Section E Structure Reports Online 69, no. 4 (2013): o532. http://dx.doi.org/10.1107/s1600536813006661.

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17

Ahmed, M., R. Sharma, D. P. Nagda, V. K. Salvi, and G. L. Talesara. "Synthetic studies of Alkoxy isoindole-1,3-diones tetra-azabenzo[f]azulenes and their Antibacterial activity." E-Journal of Chemistry 3, no. 1 (2006): 28–34. http://dx.doi.org/10.1155/2006/679374.

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3-Methylpyrazol-5-one3reacts with substituted benzaldehydes4a-din the presence of anhydrous sodium acetate to produce the corresponding 4-arylidene-5-methyl-2,4-dihydro-pyrazol-3-ones5a-dand the condensation of5a-dwith 2-bromoalkoxy-1H-isoindole-1, 3-(2H)-diones2a-cfurnished corresponding 2-[2-(4-arylidene-3-methyl-5-oxo-4,5-dihydro-pyrazol-1-yl)alkoxy]-isoindole-1,3-diones6a-l, which on cyclisation with o-phenylendiamine give titled compounds7a-l. All the synthesized compounds have been characterized by elemental analysis and spectral data and screened for their antibacterial properties again

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18

Saliu, Kuburat O., Josef Takats, and Michael J. Ferguson. "Bis[tris(3-tert-butyl-5-methylpyrazol-1-yl)hydridoborato]ytterbium(II) toluene solvate." Acta Crystallographica Section E Structure Reports Online 65, no. 6 (2009): m643—m644. http://dx.doi.org/10.1107/s1600536809017152.

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In the title compound, [Yb(C24H40BN6)2]·C7H8, the Yb atom is coordinated by two tris(3-tert-butyl-5-methylpyrazol-1-yl)hydridoborate [TptBu,Me] ligands. One ligand binds in the κ3mode, throuh three N atoms of the pyrazolyl rings, the other ligand coordinates through two N atoms of the pyrazolyl rings and the H atom attached to the central Bviaan agostic-type interaction through the B—H group of the second TptBu,Meligand, giving an overall distorted octahedral geometry. One of thetert-butyl groups is disordered over two sites, with occupancies of 0.65 and 0.35.

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19

Laarej, K., M. Bouachrine, S. Radi, S. Kertit, and B. Hammouti. "Quantum Chemical Studies on the Inhibiting Effect of Bipyrazoles on Steel Corrosion in HCl." E-Journal of Chemistry 7, no. 2 (2010): 419–24. http://dx.doi.org/10.1155/2010/273206.

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Correlation of the efficacy of some bipyrazoles,N,N-bis(3,5-dimethyl-pyrazol-1-ylmethyl)-cyclohexylamine (Bip 1),N,N-bis(3,5-dimethylpyrazol-1-ylmethyl)-ethanolamine (Bip 2),N,N-bis(3,5-dimethylpyrazol-1-ylmethyl) allylamine (Bip 3) andN,N-bis(3-carboethoxy-5-methylpyrazol-1-ylmethyl)-cyclohexylamine (Bip 4), against the corrosion of mild steel in HCl is discussed using density functional approach B3LYP/6-31G(d) calculations. The bipyrazole inhibitors exhibited the highest inhibition efficiency. The quantum chemical parameters calculated are, the highest occupied molecular orbital (HOMO), the

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20

Lipson, V. V., S. M. Desenko, M. G. Shirobokova, O. V. Shishkin, and S. V. Shishkina. "Heterocyclizations of 5-methylpyrazol-3-amine with unsaturated arylaliphatic carboxylic acid derivatives." Russian Journal of Organic Chemistry 42, no. 7 (2006): 1022–27. http://dx.doi.org/10.1134/s1070428006070153.

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21

Kumar, Mukesh, Elizabeth T. Papish, and Matthias Zeller. "Ethyl[tris(3-tert-butyl-5-methylpyrazol-1-yl)hydridoborato]zinc(II)." Acta Crystallographica Section C Crystal Structure Communications 66, no. 8 (2010): m197—m200. http://dx.doi.org/10.1107/s0108270110024674.

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22

Shvekhgeimer, M. G. A., O. A. Ushakova, V. V. Nesterov, and M. Yu Antipin. "Reaction of 1-Aryl-3-methylpyrazol-5-ones with 2-Cyanoaryldiazonium Bisulfates." Chemistry of Heterocyclic Compounds 41, no. 2 (2005): 181–86. http://dx.doi.org/10.1007/s10593-005-0124-5.

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23

Orphanos, P. I. "Inhibition of ammonium sulphate nitrification by methylpyrazol in a highly calcareous soil." Plant and Soil 143, no. 1 (1992): 145–47. http://dx.doi.org/10.1007/bf00009140.

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24

Singh, S. P., R. K. Vaid, P. Dinakar, and Lukhvinder Singh. "Mass spectra of some 1-substituted-4-acetoacetyl-3-methylpyrazol-5-ols." Organic Mass Spectrometry 23, no. 2 (1988): 140–44. http://dx.doi.org/10.1002/oms.1210230213.

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25

Attaryan, O. A., A. O. Baltayan, R. A. Tamazyan, A. G. Aivazyan, G. A. Panosyan, and G. V. Asratyan. "Synthesis and crystal structure of 3-{(2-carboxyethyl)-[2-(3-methylpyrazol-1-yl)-ethyl]amino}- and 3-{(2-carboxyethyl)[2-(5- methylpyrazol-1-yl)-ethyl]amino} propionic acids." Russian Journal of General Chemistry 79, no. 4 (2009): 870–71. http://dx.doi.org/10.1134/s1070363209040343.

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26

Journal, Baghdad Science. "Synthesis and characterization of some heterocyclic including oxazoles,Thiazoles, Pyridazines, phthalizines and Pyrazoles with evaluating of biological activity." Baghdad Science Journal 10, no. 3 (2013): 818–27. http://dx.doi.org/10.21123/bsj.10.3.818-827.

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A series of new compounds including p-bromo methyl pheno acetate [2]. N-( aminocarbonyl)–p-bromo pheno acetamide [3] , N-( aminothioyl) -p-bromo phenoacetyl amide [4], N-[4-(p-di phenyl)-1,3-oxazol-2-yl]-p-bromopheno acetamide [5],N-[4-p-di phenyl]-1,3-thiazol-2-yl-p-bromo phenoacet amide [6], p-bromopheno acetic acid hydrazide [7] , 1-N-(p-bromo pheno acetyl)-1,2-dihydro-pyridazin-3,6- dione [8], 1-N-(p-bromo pheno acetyl)-1,2-dihydro-phthalazin-3,8- dione[ 9], 1-(p-bromo pheno acetyl)-3-methylpyrazol-5-one [10] and 1-(p-bromo phenol acetyl)- 3,5-dimethyl pyrazole [11] have been synthesized.

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27

Jassim, Wissam K., A. M. Kadir, and Ibtisam K. Jassim. "Synthesis and characterization of some heterocyclic including oxazoles,Thiazoles, Pyridazines, phthalizines and Pyrazoles with evaluating of biological activity." Baghdad Science Journal 10, no. 3 (2013): 818–27. http://dx.doi.org/10.21123/bsj.2013.10.3.818-827.

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A series of new compounds including p-bromo methyl pheno acetate [2]. N-( aminocarbonyl)–p-bromo pheno acetamide [3] , N-( aminothioyl) -p-bromo phenoacetyl amide [4], N-[4-(p-di phenyl)-1,3-oxazol-2-yl]-p-bromopheno acetamide [5],N-[4-p-di phenyl]-1,3-thiazol-2-yl-p-bromo phenoacet amide [6], p-bromopheno acetic acid hydrazide [7] , 1-N-(p-bromo pheno acetyl)-1,2-dihydro-pyridazin-3,6- dione [8], 1-N-(p-bromo pheno acetyl)-1,2-dihydro-phthalazin-3,8- dione[ 9], 1-(p-bromo pheno acetyl)-3-methylpyrazol-5-one [10] and 1-(p-bromo phenol acetyl)- 3,5-dimethyl pyrazole [11] have been synthesized.

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28

NAKANO, Yoshiharu, Norihide ADACHI, and Kousaburo OHASHI. "Crystal Structure of Methyl 2-(1-(2,4-Dinitrophenyl)-3-methylpyrazol-5-yl) Acetate." Analytical Sciences 15, no. 8 (1999): 811–12. http://dx.doi.org/10.2116/analsci.15.811.

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29

Azev, Yu A., and I. V. Teplyashina. "ChemInform Abstract: Reaction of Dipyrazolylmethane Derivatives with 1-Phenyl-3-methylpyrazol-5-one." ChemInform 30, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199913151.

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30

Hadda, T., A. Kotchevar, M. Daoudi, B. Bennani, N. Larbi, and A. Kerbal. "Anti-tumour Activity of Some Polydentate N-Ligands: N,N-bis-(3- Substituted-5-Methylpyrazol-1yl Methyl) Arylamines and N,N,N,N-Tetra- [(3-Substituted-5-Methylpyrazol-1yl] Para-Phenylenediamines." Letters in Drug Design & Discovery 2, no. 8 (2005): 584–89. http://dx.doi.org/10.2174/157018005774717299.

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31

Aktan, Ebru, and Tahsin Uyar. "Hetarylazopyrazolone Dyes Based on Benzothiazole and Benzimidazole Ring Systems: Synthesis, Spectroscopic Investigation, and Computational Study." Journal of Chemistry 2017 (2017): 1–10. http://dx.doi.org/10.1155/2017/8659346.

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In this study, the synthesized coupling component 1-(2-benzothiazolyl)-3-methylpyrazol-5-one reacted with diazotised heterocyclic amines to afford six novel hetarylazopyrazolone dyes. These azo dyes based on benzothiazole and benzimidazole ring systems were characterized by spectral methods and elemental analyses. The solvatochromic behaviors of these dyes in various solvents were evaluated. The ground state geometries of the dyes were optimized using density functional theory (DFT). Solvent, acid-base, and substituent influences on the wavelength of the maximum absorption were examined in det

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32

Lobbia, Giancarlo Gioia, Giovanni Valle, Sandro Calogero, Patrizio Cecchi, Carlo Santini, and Fabio Marchetti. "Trichloro-, mono-, di- and tri-organotin(IV) derivatives of hydridotris(4-methylpyrazol-1-yl)borates." Journal of the Chemical Society, Dalton Transactions, no. 12 (1996): 2475. http://dx.doi.org/10.1039/dt9960002475.

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33

Kett, Warren C., Michael Batley, and John W. Redmond. "Heterocyclic derivatives of sugars: the formation of 1-glycosyl-3-methylpyrazol-5-ones from hydrazones." Carbohydrate Research 329, no. 1 (2000): 169–77. http://dx.doi.org/10.1016/s0008-6215(00)00165-8.

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34

Morozov, А. N., I. N. Shcherbakov, S. I. Levchenkov, and L. D. Popov. "Structure, Spectral Properties, and Complexing Ability of 1-Phenyl-3-methylpyrazol-5-one Ferrocenoyl Hydrazone." Russian Journal of General Chemistry 90, no. 2 (2020): 257–67. http://dx.doi.org/10.1134/s1070363220020152.

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35

López, Rodolfo, Gerardo León, and Alfonso Oliva. "4-Alkoxycarbonyl, 4-alkylthiocarbonyl and 5-alkoxycarbonyloxy derivatives of 1-substituted-3-methylpyrazol-5-ones." Journal of Heterocyclic Chemistry 32, no. 4 (1995): 1377–79. http://dx.doi.org/10.1002/jhet.5570320445.

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36

Seitz, Gunther, Reinhard Hoferichter, and Rolf Mohr. "Imidazole, Oxazol und N-Methylpyrazol als Dienophile in der Diels-Alder-Cycloaddition mit inversem Elektronenbedarf." Archiv der Pharmazie 322, no. 7 (1989): 415–17. http://dx.doi.org/10.1002/ardp.19893220707.

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37

Abiola, Olusegun K., and J. O. E. Otaigbe. "Adsorption Behaviour of 1-phenyl-3-methylpyrazol-5-one on Mild Steel from HCI Solution." International Journal of Electrochemical Science 3, no. 2 (2008): 191–98. http://dx.doi.org/10.1016/s1452-3981(23)15438-1.

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38

Brown, RFC, FW Eastwood, GD Fallon, SC Lee, and RP Mcgeary. "The Pyrolytic Rearrangement of 1-Alkynoyl-3-methylpyrazoles: Synthesis of Pyrazolo[1,5-a]pyridin-5-ols and Related Compounds." Australian Journal of Chemistry 47, no. 6 (1994): 991. http://dx.doi.org/10.1071/ch9940991.

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Flash vacuum pyrolysis of 1-(alkyn-2′-oyl)-3-methylpyrazoles at 650°/0.03 mm forms pyrazolo[1,5-a]pyridin-5-ols, often in high yield, which may bear substituents at C2, C3 or C7. In the absence of a 3-methyl group in the precursor, N-ethynylpyrazoles are formed in low yield. The formation of both types of product is interpreted as involving 3-(N-pyrazolyl)propadienones formed by N1 → N2 migration of the N-alkynoyl group with inversion of the three-carbon chain. The fused-ring structure of 2-methylpyrazolo[1,5-a]pyridin-5-ol (25) was established by X-ray crystallography of the O-benzoyl derivat

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39

Huang, Jiong, Lily Lee, Brian S. Haggerty, Arnold L. Rheingold, and Marc A. Walters. "Hydrotris(3,4-diphenyl-5-methylpyrazol-1-yl)borate: Control of Coordination Number via an Equatorial Substituent." Inorganic Chemistry 34, no. 16 (1995): 4268–70. http://dx.doi.org/10.1021/ic00120a037.

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40

Fujisawa, Kiyoshi, Masaya Shimizu та Edward R. T. Tiekink. "Crystal structure of chlorido{hydridotris[3-phenyl-5-methylpyrazol-1-yl-κN3]borato}copper(II), C30H28BClCuN6". Zeitschrift für Kristallographie - New Crystal Structures 236, № 1 (2021): 135–38. http://dx.doi.org/10.1515/ncrs-2020-0410.

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AbstractC30H28BClCuN6, triclinic, $P&#x203e;{1}$ (no. 2), a = 11.549(3) Å, b = 12.321(3) Å, c = 12.348(4) Å, α = 111.785(1)°, β = 116.664(3)°, γ = 97.513(1)°, V = 1361.3(7) Å3, Z = 2, Rgt(F) = 0.0440, wRref(F2) = 0.1063, T = 197 K.

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41

Huppatz, JL. "Systemic Fungicides. The Synthesis of Pyrazolo[1,5-a]pyrimidine Analogues of Carboxin." Australian Journal of Chemistry 38, no. 1 (1985): 221. http://dx.doi.org/10.1071/ch9850221.

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The synthesis of a series of pyrazolo [1,5-a] pyrimidine derivatives, structural analogues of the systemic fungicide carboxin, is described. A common intermediate incorporating structural features desirable for fungicidal activity, N-phenyl-3(5)-amino-5(3)-methylpyrazole-4- carboxamide (6), was used to prepare pyrazolo [1,5-a] pyrimidines variously substituted in positions 5 and 7 of the ring system. Bromination of N-phenyl-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide (8) occurred preferentially in the phenyl ring and the 6-bromo derivative was prepared by bromination of the corresponding 3

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42

Das, Kuheli, Belete B. Beyene, Amitabha Datta, Eugenio Garribba, and Chen-Hsiung Hung. "Electrocatalytic H2 Evolution of Bis(3,5-di-methylpyrazol-1-yl)acetate Anchored Hexa-coordinated Co(II) Derivative." Catalysis Letters 148, no. 9 (2018): 2703–8. http://dx.doi.org/10.1007/s10562-018-2477-2.

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�pshtein, N. A., L. F. Mikhaleva, V. P. Shamshin, V. P. Zelenova, B. G. Voronin, and A. I. Ermakov. "Decomposition of 1-phenyl-3-methylpyrazol-5-one at a raised temperature in the process of methylation." Pharmaceutical Chemistry Journal 21, no. 10 (1987): 749–51. http://dx.doi.org/10.1007/bf00758140.

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Azev, Yu A., and I. V. Teplyashina. "Interaction of fervenulin-4-oxide with 1-phenyl-3-methylpyrazol-5-one in the absence of bases." Pharmaceutical Chemistry Journal 32, no. 2 (1998): 97–98. http://dx.doi.org/10.1007/bf02464173.

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Shukla, J. P., M. S. Nagar, and S. K. Arora. "Protolytic equilibria of several 4-acyl-substituted 1-phenyl-3-methylpyrazol-5-ones in dioxane-water mixtures." Journal of Physical Organic Chemistry 4, no. 11 (1991): 667–74. http://dx.doi.org/10.1002/poc.610041104.

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Kett, Warren C., Michael Batley, and John W. Redmond. "ChemInform Abstract: Heterocyclic Derivatives of Sugars: The Formation of 1-Glycosyl-3-methylpyrazol-5-ones from Hydrazones." ChemInform 32, no. 6 (2001): no. http://dx.doi.org/10.1002/chin.200106173.

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LOPEZ, R., G. LEON, and A. OLIVA. "ChemInform Abstract: 4-Alkoxycarbonyl, 4-Alkylthiocarbonyl and 5-Alkoxycarbonyloxy Derivatives of 1-Substituted-3-methylpyrazol-5-ones." ChemInform 26, no. 51 (2010): no. http://dx.doi.org/10.1002/chin.199551132.

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Hartmann, Manfred, Hans-Jürgen Bauer, and Kurt Wermann. "Biocide Polymere; Modifizierung von Poly(ethylen-alt-maleinsäure) mit 3-Amino-1,2,4-triazol und 3(5)-Methylpyrazol." Zeitschrift für Chemie 26, no. 10 (2010): 369–71. http://dx.doi.org/10.1002/zfch.19860261006.

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Fujisawa, Kiyoshi, Makoto Yabe та Edward R. T. Tiekink. "Crystal structure of carbonyl{hydridotris[3-phenyl-5-methylpyrazol-1-yl]borato-κ3N,N′N′′}copper(I), C31H28BCuN6O". Zeitschrift für Kristallographie - New Crystal Structures 235, № 6 (2020): 1507–9. http://dx.doi.org/10.1515/ncrs-2020-0372.

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Pettinari, C., C. Santini, D. Leonesi, and P. Cecchi. "Synthesis and characterization of some zinc, cadmium and mercury(II) derivatives of bis(4-methylpyrazol-1-yl) alkanes." Polyhedron 13, no. 10 (1994): 1553–62. http://dx.doi.org/10.1016/s0277-5387(00)83450-6.

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