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Journal articles on the topic 'Synthesis of Pyrazoles'

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Published: 5 June 2025

Last updated: 1 August 2025

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1

M., K. A. IBRAHIM, H. H. ELGHANDOUR A., S.M. ABDBL-SAYED G., and S.M. ABDEL FATTAH A. "Synthesis of Pyrazoles and Fused Pyrazoles. Novel Synthesis of Pyrano[2,3-c]pyrazole, Thieno[2,3-c]pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives." Journal of Indian Chemical Society Vol. 74, Mar 1997 (1997): 206–8. https://doi.org/10.5281/zenodo.5885902.

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Department of Chemistry, Faculty of Science, Cairo University, Giza, A. R. Egypt <em>Manuscript received 17 November 1994, revised 26 July 1995, accepted 28 September 1995</em> 3-Metbyl-1-thiocarbamoylpyrazoi-5-one (1) reacted with <em>p</em>-metbylpbenscyl bromide to give 3-metbyl-1(4-tbiazol-2-yl)pyrazol-5-one (2). Compounds 1 and 2 were reacted with reagents such as α-cyanocinnamo. benzaldehyde, elemental suJphurlmalononltrlle, benzenediazomum chloride, pyrazol-5-yl-diazonium chloride malononitriie, and ethyl acetoacetate to afford pyrano[2,3-<em>c</em>]pyrazoles (4, 6) Pyra

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2

Elnagdi, Mohamed Hilmy, Ahmed Hafez Hussien Elghandour, Kamal Usef Sadek, and Mahmoud Mohamed Mahfouz Ramiz. "Studies on Condensed Pyrazoles. A New Route for Synthesis of Pyrazolo[4,3-c]pyrazoles." Zeitschrift für Naturforschung B 44, no. 8 (1989): 951–54. http://dx.doi.org/10.1515/znb-1989-0816.

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A novel synthesis of pyrazolo[4,3-c]pyrazoles via 1,5-dipolar cyclization of products of coupling of 2,3-dimethyl-1-phenyl-5-oxo-3-pyrazolin-4-diazonium chloride with active methylene reagents is reported.

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3

Chauhan, Pankaj, Suruchi Mahajan, and Dieter Enders. "Asymmetric synthesis of pyrazoles and pyrazolones employing the reactivity of pyrazolin-5-one derivatives." Chemical Communications 51, no. 65 (2015): 12890–907. http://dx.doi.org/10.1039/c5cc04930j.

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The various catalytic asymmetric strategies employing organo- and metal-catalysts utilized pyrazolin-5-one derivatives for the synthesis of potentially bioactive enantiopure pyrazoles and pyrazolones are presented.

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4

Alsayari, Abdulrhman, Abdullatif Bin Muhsinah, Yahya I. Asiri, et al. "Arylhydrazono/Aryldiazenyl Pyrazoles: Green One-Pot Solvent-Free Synthesis and Anticancer Evaluation." Letters in Organic Chemistry 17, no. 10 (2020): 772–78. http://dx.doi.org/10.2174/1570178617666200320104923.

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The aim of this study was to synthesize and evaluate the biological activity of pyrazole derivatives, in particular, to perform a “greener” one-pot synthesis using a solvent-free method as an alternative strategy for synthesizing hydrazono/diazenyl-pyridine-pyrazole hybrid molecules with potential anticancer activity. Effective treatment for all types of cancers is still a long way in the future due to the severe adverse drug reactions and drug resistance associated with current drugs. Therefore, there is a pressing need to develop safer and more effective anticancer agents. In this context, s

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5

(MRS), B.D. SARAF, and N. WADODKAR K. "Synthesis of some New 5-(2-Hydroxyphenyl)-3-methyl-4-(1- acetyl-5-aryl-2-pyrazolin-3-yl)pyrazoles and 1-Phenyl-5- (2-hydroxyphenyl)-3-methyl-4-(1-phenyl-5-aryl-2- pyrazolin-3-yl)pyrazoles." Journal of Indian Chemical Society Vol. 70, Jul 1993 (1993): 643–44. https://doi.org/10.5281/zenodo.5917738.

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Department of Chemistry, Vidarbha Mahavidylaya, Amravati-444 604 <em>Manuscript received 4 October 1991, revised 19 January 1993, accepted 1 February </em>1993 synthesis of some New 5-(2-Hydroxyphenyl)-3-methyl-4-(1- acetyl-5-aryl-2-pyrazolin-3-yl)pyrazoles and 1-Phenyl-5-Synthesis of some New 5-(2-Hydroxyphenyl)-3-methyl-4-(1-(2-hydroxyphenyl)-3-methyl-4-(1-phenyl-5-aryl-2-pyrazolin-3-yl)pyrazoles          

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6

Queiroz, Jaqueline E., Lucas D. Dias, Giuliana M. Vila Verde, Gilberto L. B. Aquino, and Ademir J. Camargo. "An Update on the Synthesis and Pharmacological Properties of Pyrazoles Obtained from Chalcone." Current Organic Chemistry 26, no. 2 (2022): 81–90. http://dx.doi.org/10.2174/1385272826666220119110347.

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Abstract: A review concerning the synthesis and pharmacological properties of pyrazoles obtained from Chalcone described in the literature over the last 5 years (2016-2020) was presented and discussed. Among the synthetic approaches for pyrazoles described so far, the cyclization and acetylation method of α,β-unsaturated chalcones, and substituted hydrazine were selected and analyzed. 105 pyrazole derivatives (3-107) were evaluated as well as their pharmacological activities, namely, antineoplastic, anti-inflammatory, antioxidant, antibacterial, antifungal, antimycobacterial, antiplasmodial, A

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7

Lindsay-Scott, Peter J., and Eloise Rivlin-Derrick. "Regiocontrolled Synthesis of 6,7-Dihydro-4H-pyrazolo[5,1-c][1,4]oxazines." Synthesis 52, no. 01 (2019): 105–18. http://dx.doi.org/10.1055/s-0037-1610734.

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Synthetic access to 6,7-dihydro-4H-pyrazolo[5,1-c][1,4]oxazines has been achieved in 3–4 steps from commercially available pyrazoles. Optimization of a protected hydroxyethyl group on N1 enabled the regiocontrolled construction of pyrazole-5-aldehydes in high yields; subsequent deprotection and reduction generated fused heterocyclic scaffolds bearing multiple substitution patterns. Moreover, the intermediate pyrazole lactols were shown to be versatile synthetic building blocks.

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8

A., Rajeshwar Rao, Gopinath G., V. Madhuri J., and Satyanarayana S. "Synthesis of pyrazole and pyrazole amidocobaloximes." Journal of Indian Chemical Society Vol. 81, Jan 2004 (2004): 58–60. https://doi.org/10.5281/zenodo.5829945.

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Department of Chemistry, Osmania University, Hyderabad-500 007, India <em>E-mail</em> : ssnsirasani @yahoo.com <em>Manuscript received 23 September 2002, revised 23 April 2003. accepted 11 July 2003</em> A series of cyano (ligand) cobaloximes have been prepared where, the ligand is pyrazole (Pz), 1-(acetamido)pyrazole (Apz), 1-(<em>N</em>-methylacetamido)pyrazole (MAPz), 1-(acetamido)-3,5-dimethylpyrazole (MADMPz). The complex K[(CN)Co(D<sub>2</sub>H<sub>2</sub>)SCN] reacts with cthanolic solution of pyrazole or pyrazole amido ligands to form mixed ligand complexes. In all these complexes, the

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9

Lam, Linh, Sang H. Park, and Joseph Sloop. "Synthesis and Characterization of 3-Methyl-1-(4-(trifluoromethyl)phenyl)indeno [1,2-c]pyrazol-4(1H)-one." Molbank 2022, no. 4 (2022): M1483. http://dx.doi.org/10.3390/m1483.

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Pyrazoles have potential applications in the agrochemical and medicinal chemistry industries as pesticides, anti-inflammatory medications, and antitumor drugs. Fluorinated fused-ring pyrazoles may also possess medicinally useful properties. Herein, we report the acid-catalyzed synthesis of a new tricyclic, trifluoromethylated indenopyrazole, 3-methyl-1-(4-(trifluoromethyl)phenyl)indeno[1,2-c]pyrazol-4(1H)-one, from 2-acetyl-1,3-indanedione and 4-trifluoromethylphenylhydrazine. This isomeric pyrazole was obtained in yields ranging from 4–24%. NMR spectroscopic characterization and elemental ana

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10

Noori, Zahra, Miquel Solà, Clara Viñas, Francesc Teixidor, and Jordi Poater. "Unraveling aromaticity: the dual worlds of pyrazole, pyrazoline, and 3D carborane." Beilstein Journal of Organic Chemistry 21 (February 21, 2025): 412–20. https://doi.org/10.3762/bjoc.21.29.

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A new series of o-carborane-fused pyrazoles has been recently successfully synthesized. This fusion was expected to create a hybrid 3D/2D aromatic system, combining the 3D aromaticity of o-carborane with the 2D aromaticity of pyrazole. However, while the boron cage retains its aromatic character, the pyrazole’s aromaticity is lost. As a result, rather than forming o-carborane-fused pyrazoles, the synthesis yielded o-carborane-fused pyrazolines, which are non-aromatic. The limited overlap between the π molecular orbitals (MOs) of the planar heterocycle and the n + 1 MOs of the carborane prevent

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11

Sophy, Mohamed Ahmed Elian, and Mohamed Ahmed Mahmoud Abdel Reheim. "Synthesis of Some New 1, 3, 4-Oxadiazole, Pyrazole, and Pyrimidine Bearing Thienopyrazole Moieties." Current Organic Synthesis 17, no. 8 (2020): 661–70. http://dx.doi.org/10.2174/1570179417999200730215318.

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Aim and Objective: According to the literature survey, pyrazole is a unique template that is associated with several biological activities. This article highlighted the research work of many researchers reported in the literature for synthesis and different pharmacological activities of the pyrazole nucleus. In the present work, pyrazol- 3-one 1 was reacted with cyanoacetic acid hydrazide and elemental sulfur to afford the corresponding thieno[3,2-c]pyrazol-6-carbohydrazide 3 derivatives. The latter compound reacted with some electrophilic reagents such as DMF-DMA, triethylorthoformate, arylid

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12

Milišiūnaitė, Vaida, Rūta Paulavičiūtė, Eglė Arbačiauskienė, Vytas Martynaitis, Wolfgang Holzer, and Algirdas Šačkus. "Synthesis of 2H-furo[2,3-c]pyrazole ring systems through silver(I) ion-mediated ring-closure reaction." Beilstein Journal of Organic Chemistry 15 (March 14, 2019): 679–84. http://dx.doi.org/10.3762/bjoc.15.62.

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Fused pyrazole ring systems are common structural motifs of numerous pharmaceutically important compounds. Nevertheless, access to derivatives of the aromatic 2H-furo[2,3-c]pyrazole ring system is still quite limited, and their chemistry and functional properties remain largely underexplored. The current study investigates routes to construct this system from easily accessible starting materials using metal-catalyzed reactions. A simple and efficient procedure to access the 2H-furo[2,3-c]pyrazole ring system was developed by employing the silver(I) ion-mediated ring-closure reaction of 4-alkyn

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13

Secrieru, Alina, Paul Michael O’Neill, and Maria Lurdes Santos Cristiano. "Revisiting the Structure and Chemistry of 3(5)-Substituted Pyrazoles." Molecules 25, no. 1 (2019): 42. http://dx.doi.org/10.3390/molecules25010042.

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Pyrazoles are known as versatile scaffolds in organic synthesis and medicinal chemistry, often used as starting materials for the preparation of more complex heterocyclic systems with relevance in the pharmaceutical field. Pyrazoles are also interesting compounds from a structural viewpoint, mainly because they exhibit tautomerism. This phenomenon may influence their reactivity, with possible impact on the synthetic strategies where pyrazoles take part, as well as on the biological activities of targets bearing a pyrazole moiety, since a change in structure translates into changes in propertie

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14

Klein, Jean F., Jean Claude Pommelet, Josselin Chuche, José Elguero, Pilar Goya, and Ana Martinez. "SO2 extrusion in 1,2,6-thiadiazine 1,1-dioxides: a novel synthesis of pyrazoles." Canadian Journal of Chemistry 71, no. 3 (1993): 410–12. http://dx.doi.org/10.1139/v93-060.

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A novel synthesis of the pyrazole ring involving SO2 extrusion by flow vacuum pyrolysis in the 1,2,6-thiadiazine 1,1-dioxide system is described. The reaction has potential industrial significance for routes to pyrazoles or functionalized pyrazoles that do not involve hydrazines.

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15

Vydzhak, Roman N., and Svitlana Yа Panchishin. "Synthesis of 2-aminoethyl derivatives of pyrazolo[4,3-c]pyrazoles." Ukrainica Bioorganica Acta 19, no. 2 (2024): 10–20. https://doi.org/10.15407/bioorganica2024.02.010.

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Preparative method for the preparation of 2-aminoethyl derivatives of pyrazolo[4,3-c]pyrazoles is presented. Alkylation of 1-alkyl-3-methyl-1,4-dihydropyrazolo[4,3-c]pyrazoles with 2-(2-bromomethyl)-1H-isoindole-1,3(2H)-dione and chloroacetonitrile was carried out. In all cases, mixtures of isomeric products of 1- and 2-alkylation with isomer ratios of 1 : 0.8 were obtained. The mixtures of isomers were separated by chromatography and the target compounds did not contain impurities of another isomer. All phthalimide derivatives of pyrazolo[4,3-c]pyrazoles were converted into the corresponding

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16

Zouaoui, Emna, and Mohamed Moncef El Gaïed. "Synthesis of Trifluoromethyl Heterocyclic Compounds." Journal of Chemical Research 2003, no. 4 (2003): 242–46. http://dx.doi.org/10.1177/1747519803200300404.

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17

Usami, Yoshihide, Kodai Sumimoto, Azusa Kishima, Yuya Tatsui, Hiroki Yoneyama, and Shinya Harusawa. "Synthesis of Dihydropyrano[3,2-c]pyrazoles via Double Bond Migration and Ring-Closing Metathesis." Molecules 24, no. 2 (2019): 296. http://dx.doi.org/10.3390/molecules24020296.

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Three types of pyrazole-fused heterobicycles, i.e., 1,5-, 1,7-, and 2,5-dihydropyrano[3,2-c]pyrazoles, were synthesized from 4-allyloxy-1H-pyrazoles. A sequence of the Claisen rearrangement of 4-allyloxy-1H-pyrazoles, ruthenium-hydride-catalyzed double bond migration, O-allylation, and ring-closing metathesis was employed in this study.

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18

Lellek, Vit, Cheng-yi Chen, Wanggui Yang, Jie Liu, Xuebao Ji, and Roger Faessler. "An Efficient Synthesis of Substituted Pyrazoles from One-Pot Reaction of Ketones, Aldehydes, and Hydrazine Monohydrochloride." Synlett 29, no. 08 (2018): 1071–75. http://dx.doi.org/10.1055/s-0036-1591941.

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An efficient, one-pot and metal-free process for the preparation of 3,5-disubstituted and 3,4,5-trisubstituted pyrazoles on multi-gram scale was developed. One-pot condensation of ketones, aldehydes and hydrazine monohydrochloride readily formed pyrazoline intermediates under mild conditions. Oxidation of pyrazolines, in situ, employing bromine afforded a wide variety of pyrazoles. The methodology offers a fast, and often chromatography-free protocol for the synthesis of 3,4,5-substituted pyrazoles in good to excellent yields. Alternatively, a more benign oxidation protocol affords 3,5-disubst

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19

Mantzanidou, Martha, Eleni Pontiki, and Dimitra Hadjipavlou-Litina. "Pyrazoles and Pyrazolines as Anti-Inflammatory Agents." Molecules 26, no. 11 (2021): 3439. http://dx.doi.org/10.3390/molecules26113439.

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The five-membered heterocyclic group of pyrazoles/pyrazolines plays important role in drug discovery. Pyrazoles and pyrazolines present a wide range of biological activities. The synthesis of the pyrazolines and pyrazole derivatives was accomplished via the condensation of the appropriate substituted aldehydes and acetophenones, suitable chalcones and hydrazine hydrate in absolute ethanol in the presence of drops of glacial acetic acid. The compounds are obtained in good yields 68–99% and their structure was confirmed using IR, 1H-NMR, 13C-NMR and elemental analysis. The novel derivatives were

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20

Karayeva, A. R., M. I. Shatirova, B. A. Mamedov, Sh F. Nagieva, and L. I. Gadzhiyeva. "Synthesis of 3-Alkyl-5-(diethylaminomethyl)-1-(1,3-thiazole)pyrazoles." Žurnal organičeskoj himii 60, no. 1 (2024): 104–8. https://doi.org/10.31857/s0514749224010091.

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By the reaction of 3-alkyl-5-(diethylaminomethyl) pyrazoles with chloroanhydride of monochloroacetic acid, the pyrazoles with chloromethyl carbonyl substituent have been synthesized. Due to presence of reactive COCH2Cl groups in a molecule, the pyrazoles have been subjected to heterocyclization with thicarbamides (thiobenzamide, thicarbamide and phenylthiocarbamide) in the presence of triethyleamine in a medium of ethanol, as a result of which the previously unknown 3-alkyl-5-diethylaminomethyl-1-(1,3-thiazol)substituted pyrazole derivatives have been obtained.

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21

Alsayari, Abdulrhman, Yahya I. Asiri, Abdullatif Bin Muhsinah, and Mohd Zaheen Hassan. "Synthesis and antimicrobial activity of aryldiazenyl/arylhydrazono pyrazoles." Journal of Chemical Research 45, no. 11-12 (2021): 1093–99. http://dx.doi.org/10.1177/17475198211057461.

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We report the design, synthesis, and in vitro antimicrobial evaluation of functionalized pyrazoles containing a hydrazono/diazenyl moiety. Among these newly synthesized derivatives, 4-[2-(4-chlorophenyl)hydrazono]-5-methyl-2-[2-(naphthalen-2-yloxy)acetyl]-2,4-dihydro-3 H-pyrazol-3-one is a promising antimicrobial agent against Staphylococcus aureus (minimum inhibitory concentration 0.19 μg mL−1). Structure–activity relationship studies reveal that the electronic environment on the distal phenyl ring has a considerable effect on the antimicrobial potential of the hybrid analogues. Molecular doc

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22

Kumar, Manoj, Shashi Sharma, Hardeep Singh Tuli, and Vinit Parkash. "Ferrocenyl Substituted Pyrazoles, Synthesis via novel route, Spectral Investigations and Their Biological Studies." Oriental Journal of Chemistry 35, no. 2 (2019): 863–69. http://dx.doi.org/10.13005/ojc/350250.

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Ferrocenyl substituted heterocyclic compounds have wide range of medicinal approach. The synthesis of ferrocenyl substituted pyrazole is the new concern in these compounds with enhanced biological activities. This work focus on synthesis of ferrocenyl substituted pyrazoles via novel route. The synthesis of 1-phenyl-3-ferrocenyl-pyrazole was investigated involving Friedel Crafts Acylation like reaction conditions. The reaction proceeded through three stages using addition cyclo-condensation of acetyl ferrocene with phenyl hydrazine followed by cyclization using cyclizing reagent iodine in prese

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23

Vane, Vilas, and Suresh Jadhava. "The synthesis of pyrazole derivatives from hydrazone using Amberlyst A26 resin under ultrasonic radiation." Current Chemistry Letters 14, no. 1 (2025): 139–48. http://dx.doi.org/10.5267/j.ccl.2024.8.003.

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Pyrazoles are highly versatile and find applications in various industries including chemicals, pharmaceuticals, polymers, medications, and agriculture. Pyrazoles and their analogues exhibit a range of biological activities, including anti-inflammatory, anti-tuberculosis, antibacterial, antifungal, anti-cancer, and anti-diabetic effects. In this context, this investigation focuses on the synthesis of pyrazoles containing heterocyclic components using Amberlite resin in reactions with ultrasonic irradiation. Synthesized pyrazoles containing heterocyclic components are intermediates of the apixa

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24

Urbonavičius, Arminas, Sonata Krikštolaitytė, Aurimas Bieliauskas, et al. "Synthesis and Characterization of New Pyrano[2,3-c]pyrazole Derivatives as 3-Hydroxyflavone Analogues." Molecules 28, no. 18 (2023): 6599. http://dx.doi.org/10.3390/molecules28186599.

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In this paper, an efficient synthetic route from pyrazole-chalcones to novel 6-aryl-5-hydroxy-2-phenylpyrano[2,3-c]pyrazol-4(2H)-ones as 3-hydroxyflavone analogues is described. The methylation of 5-hydroxy-2,6-phenylpyrano[2,3-c]pyrazol-4(2H)-one with methyl iodide in the presence of a base yielded a compound containing a 5-methoxy group, while the analogous reaction of 5-hydroxy-2-phenyl-6-(pyridin-4-yl)pyrano[2,3-c]pyrazol-4(2H)-one led to the zwitterionic 6-(N-methylpyridinium)pyrano[2,3-c]pyrazol derivative. The treatment of 5-hydroxy-2,6-phenylpyrano[2,3-c]pyrazol-4(2H)-one with triflic

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25

Ramadan, El Sayed, Essam M. Sharshira, Ramadan I. El Sokkary, and Noussa Morsy. "Synthesis and antimicrobial evaluation of some heterocyclic compounds from 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes." Zeitschrift für Naturforschung B 73, no. 6 (2018): 389–97. http://dx.doi.org/10.1515/znb-2018-0009.

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AbstractA new series of chalcones, pyrazolinyl-pyrazoles, pyrazole-4-carbaldehyde oximes, pyrazole-4-carbonitriles, 5-pyrazolyl-1,2,4-triazolidine-3-thiones, and Knoevenagel condensation products was synthesized from 3-aryl-1-phenyl-1H-pyrazole-4-carbaldehydes. Most reactions were carried out either without solvent or in the presence of water as a green solvent. The structure of synthesized compounds was characterized by spectral and elemental analysis. The synthesized compounds were tested in vitro for their antimicrobial activity against Escherichia coli, Staphylococcus aureus, and Candida a

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26

Petek, Nejc, and Uroš Grošelj. "Photoinduced Ring Opening of Methyl 1-Aryl-5-oxo-6,7-dihydro-1H,5H-pyrazolo[1,2-a]pyrazole-2-carboxylates in the Presence of Diaryl Disulfides." Molbank 2023, no. 2 (2023): M1670. http://dx.doi.org/10.3390/m1670.

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Among the methods used for the synthesis of functionalized heterocyclic compounds, photochemistry has gained immense popularity due to the reactivity of intermediates in photoinduced reactions. In this study, we report on the effect of diaryl disulfides as hydrogen atom transfer catalysts on the photoinduced transformations of pyrazolo[1,2-a]pyrazolones. After excitation with visible light, these compounds are susceptible to C–N bond cleavage, followed by intermolecular hydrogen atom abstraction. By modifying the reaction conditions, we have developed two novel methods for the synthesis of hig

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Meshcheryakova, Anna A., Ekaterina A. Konstantinova, and Vitaliy V. Sorokin. "The synthesis of 5-amino-3-aryl-1H-pyrazole-4-carbonitriles based on hydrazines and benzhydrazides under ultrasonic activation conditions." Izvestiya of Saratov University. Chemistry. Biology. Ecology 24, no. 3 (2024): 249–61. http://dx.doi.org/10.18500/1816-9775-2024-24-3-249-261.

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Pyrazoles containing amino and carbonitrile groups have a wide range of biological activities, including antimicrobial, antiinflammatory, antitumor, antioxidant, and are used to create pesticides and dyes. Also, these compounds are synthons for the preparation of various polyheterocyclic compounds. New potentially biologically active 5-amino-3-aryl-1H-pyrazole-4-carbonitriles containing pharmacophoric substituents have been obtained via three-component condensation reactions of malonic dinitrile with substituted aromatic aldehydes and benzhydrazides or hydrazines. This work considers the limit

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28

Jansa, Josef, Ramona Schmidt, Ashenafi Damtew Mamuye, et al. "Synthesis of tetrasubstituted pyrazoles containing pyridinyl substituents." Beilstein Journal of Organic Chemistry 13 (May 12, 2017): 895–902. http://dx.doi.org/10.3762/bjoc.13.90.

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A synthesis of tetrasubstituted pyrazoles containing two, three or four pyridinyl substituents is described. Hence, the reaction of 1,3-dipyridinyl-1,3-propanediones with 2-hydrazinopyridine or phenylhydrazine, respectively, affords the corresponding 1,3,5-trisubstituted pyrazoles. Iodination at the 4-position of the pyrazole nucleus by treatment with I2/HIO3 gives the appropriate 4-iodopyrazoles which served as starting materials for different cross-coupling reactions. Finally, Negishi cross-coupling employing organozinc halides and Pd catalysts turned out to be the method of choice to obtain

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I.H. El-Qaliei, Mohamed, Sayed A.S. Mousa, Esam A. Ishak, Hamdi M.D. Nasr, Modather F Hussein, and Abdallah M.A. Hassane. "Synthesis, characterization, antimicrobial, antioxidant activities, and in silico study of new azo disperse dyes containing pyrazole and pyrazolo[1,5-a]pyrimidine rings." Bulletin of the Chemical Society of Ethiopia 39, no. 7 (2025): 1411–24. https://doi.org/10.4314/bcse.v39i7.13.

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New N,N-dimethyl-N'-(5-oxo-4-(aryldiazenyl)-2,5-dihydro-1H-pyrazol-3-yl)formimidamide 5a-c are formed by reaction of 5-amino-1H-pyrazol-3(2H)-one derivatives 4a-c with N,N-dimethylformamide dimethyl acetal (DMF-DMA). Compounds 5a-c serve as excellent precursors for the synthesis of new disazo pyrazole disperse dyes, When refluxed with hydrazine hydrate or active methylene reagents 8a,b, leading to N''-(3-hydroxy-4-(arylaza)-1H-pyrazol-5-yl)formimidohydrazide 7a-c or pyrazolo[1,5-a]. pyrimidines 11a–e. In vitro studies were carried out to evaluate antioxidant properties of the produced compound

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30

Ameziane El Hassani, Issam, Khouloud Rouzi, Hamza Assila, Khalid Karrouchi, and M’hammed Ansar. "Recent Advances in the Synthesis of Pyrazole Derivatives: A Review." Reactions 4, no. 3 (2023): 478–504. http://dx.doi.org/10.3390/reactions4030029.

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Pyrazole, characterized by a five-membered heterocyclic structure featuring two neighboring nitrogen atoms, serves as a core element. Pyrazoles hold a privileged status as versatile frameworks in various sectors of the chemical industry, including medicine and agriculture. Previous reviews have extensively highlighted the significance of pyrazoles and their diverse biological activities, encompassing roles such as antituberculosis, antimicrobial, antifungal, anti-inflammatory, anticancer, and antidiabetic agents. Consequently, they have garnered substantial interest from researchers. The aim o

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31

Aegurla, Balakrishna, Nisha Jarwal, and Rama Krishna Peddinti. "Denitrative imino-diaza-Nazarov cyclization: synthesis of pyrazoles." Organic & Biomolecular Chemistry 18, no. 31 (2020): 6100–6107. http://dx.doi.org/10.1039/d0ob01200a.

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This iodine-catalysed expedient process furnished functionally-rich pyrazoles regioselectively in ethanol under aerobic conditions. The cascade reaction for the pyrazole formation proceeds through enamine–imino diaza-Nazarov 4π-electrocyclization.

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Rey, Marine, and Stéphane Beaumont. "Molybdenum-Mediated One-Pot Synthesis of Pyrazoles from Isoxazoles." Synthesis 51, no. 20 (2019): 3796–804. http://dx.doi.org/10.1055/s-0039-1690615.

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A one-pot approach for the direct synthesis of substituted pyrazoles from isoxazoles is reported. The process involves isoxazole N–O bond cleavage mediated by a molybdenum complex, in situ hydrolysis of the resulting β-amino enone to the corresponding 1,3-diketone, followed by pyrazole formation in the presence of hydrazine or substituted hydrazine. Good to excellent yields and regioselectivities are obtained with nonsymmetric isoxazoles. By using readily available starting materials, a wide range of substituted pyrazoles may be synthesized by this method.

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Berl, Jelena K., Christian Czaschke, Ann-Kathrin Pramor, Christian B. W. Stark, and Joachim Thiem. "Serendipitous Conversion of an Acetylamino Dideoxy-Octonic Acid Derivate into a Functionalized Carbohydrate–Pyrazole Conjugate and Investigation of the Method´s General Applicability." Molecules 29, no. 20 (2024): 4885. http://dx.doi.org/10.3390/molecules29204885.

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By treatment of the peracetylated methylester of 4-acetylamino-2,4-dideoxy-d-glycero-d-galacto-octonic acid (ADOA-PAE) with nitrosyl tetrafluoroborate, a serendipitous formation of a highly functionalized carbohydrate–pyrazole conjugate was observed in 95% yield. This observation is remarkable, as it involves a five-step one-pot synthesis that proceeds via an 1,3-acyl shift and a 1,5-electrocyclization, which usually requires thermal conditions; however, the reaction occurred at a temperature of 0 °C. Additionally, the excellent yield of the carbohydrate-decorated pyrazole and the regiospecifi

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Kumar, Manoj, Shashi Sharma, Hardeep Singh Tuli, and Rajshree Khare. "A Novel Synthesis, Characterization and Biological Studies of Ferrocenyl Substituted Pyrazoles." Asian Journal of Chemistry 31, no. 12 (2019): 2729–32. http://dx.doi.org/10.14233/ajchem.2019.22161.

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It has been discovered that ferrocenyl substituted heterocyclic compounds have wide scope of restorative methodology. The combination of ferrocenyl substituted pyrazole is the new class in these compounds with upgraded natural activity. This work center around blend of ferrocenyl substituted pyrazoles through novel course. The combination of 1-phenyl-3-ferrocenyl-pyrazole was examined including addition-cyclocondensation like response conditions. The response continued through three phases using of expansion cyclo-buildup of acetyl ferrocene with phenyl hydrazine pursued by cyclizing reagent i

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35

El-Telbani, Emad M., Ibrahim Radini, and Sameh R. Elgogary. "Syntheses of tricyclic fused quinoxaline ring systems: Pyrazoloquinoxalines (a-review)." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 35, no. 02 (2025): 279. https://doi.org/10.59467/ijhc.2025.35.279.

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Quinoxaline derivatives have gained significant interest due to their diverse pharmacological activity and have been included in numerous marketed drugs used to treat of various diseases. Examples include glecaprevir (Mavyret), voxilaprevir (Vosevi), Balversa (L01EX16) (erdafitinib), carbadox, XK469R (NSC698215), and becampanel (AMP397). Among the five-membered fused tricyclic quinoxalines ring systems, the pyrazoloquinolines belong to the azaheterocyclic group as derivatives of quinoxalines and pyrazoles and have characterized by many biological and pharmaceutical properties. There are three

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36

Baeva, L. A., and R. R. Gataullin. "Modern Approaches to the Synthesis of Pyrazoles (A Review)." Журнал общей химии 94, no. 1 (2024): 29–55. http://dx.doi.org/10.31857/s0044460x24010034.

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The article analyzes publications that present the results of studies of modern approaches to the synthesis of new and known heterocycles with a pyrazole fragment, as well as syntheses aimed at expanding the library of compounds of this series from hydrazines, hydrazides, semi- or thiosemicarbazides, diazo compounds, hydrazonyl chlorides. Some examples are shown that use approaches to the synthesis of pyrazoles through multicomponent reactions involving amines and hydroxamic acid or an amine and enaminoketone. References are provided to publications that reflect the results of studies of the b

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37

Nikpour, Farzad, Sara Zandi, and Mahnaz Sharafi-Kolkeshvandi. "Electrochemically Catalyzed N–N Coupling and Ring Cleavage Reaction of 1H-Pyrazoles." Synthesis 53, no. 19 (2021): 3591–96. http://dx.doi.org/10.1055/s-0040-1706050.

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AbstractThe electrocatalyzed N–N coupling and ring cleavage reaction of 3-methyl-, 3,5-dimethyl-, 3-methyl-5-phenyl- and 3,5-diphenyl-1H-pyrazole was investigated and led to the electro-organic synthesis of new heterocyclic compounds. The results revealed that electrochemically produced 1H-pyrazoleox plays the role of acceptor in a reaction with the starting molecule via a N–N coupling and ring cleavage reaction of pyrazoles. The proposed reaction sequence consists of anodic oxidation, dimerization, rearrangement and reduction. The electrochemically catalyzed reactions were accomplished under

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38

Muhammad, Zeinab A., Fatimah Alshehrei, Mohie E. M. Zayed, Thoraya A. Farghaly, and Magda A. Abdallah. "Synthesis of Novel Bis-pyrazole Derivatives as Antimicrobial Agents." Mini-Reviews in Medicinal Chemistry 19, no. 15 (2019): 1276–90. http://dx.doi.org/10.2174/1389557519666190313095545.

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Background: bis-heterocycles especially those containing pyrazole moiety display much better antibacterial activity than mono heterocycles. Objective: Herein, we synthesised a series of new bis-pyrazoles and investigated their antimicrobial agents. Methods: A novel series of bis-pyrazole derivatives have been synthesized in good yield by coupling reaction of cyanoacetic acid 4-[(2-cyano-acetyl)-hydrazonomethyl]-benzylidene-hydrazide with a number of diazonium salts of aromatic amines in DMF in the presence of NaOH. Refluxing of the produced hydrazones with hydrazine-hydrate in ethanolic soluti

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Al-Zaydi, Khadijah Mohamed, Mariam Abd Alha Al-Shiekh, and Ebtisam Abdel-Aziz Hafez. "Enaminonitriles in Heterocyclic Synthesis: New Routes for the Synthesis of Some Novel Azolo[1,5-a]pyrimidine, Pyrimido[1,2-a]benzimidazole, Pyrido[1,2-a]benimdazole, Pyrazolo[3,4-b]pyridine, Pyrazole and Pyrimidine Derivatives." Journal of Chemical Research 2000, no. 1 (2000): 13–15. http://dx.doi.org/10.3184/030823400103165716.

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40

Potapov, Andrei S., Evgenia A. Nudnova, Vladimir D. Ogorodnikov, Tatiana V. Petrenko, and Andrei I. Khlebnikov. "Synthesis of New Bitopic Tetra(pyrazolyl)-Ligands with Neopentane and O-Xylene Backbones." Scientific World Journal 2012 (2012): 1–5. http://dx.doi.org/10.1100/2012/798271.

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Several new bitopic pyrazole-containing ligands were prepared from the corresponding pyrazoles and tetrahalogen or tetratosyloxy derivatives of o-xylene and neopentane in a superbasic medium (KOH-DMSO).

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41

IBRAHIM, M. K. A., A. H. H. ELGHANDOUR, G. S. M. ABDEL-SAYED, and A. S. M. ABDEL FATTAH. "ChemInform Abstract: Synthesis of Pyrazoles and Fused Pyrazoles. Novel Synthesis of Pyrano[2,3-c]pyrazole, Thieno[2,3-c]pyrazole and Pyrazolo[3,4-b]pyridine Derivatives." ChemInform 29, no. 27 (2010): no. http://dx.doi.org/10.1002/chin.199827039.

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Sun, Pengfei, Daoshan Yang, Wei Wei, et al. "DMSO-promoted regioselective synthesis of sulfenylated pyrazoles via a radical pathway." Organic Chemistry Frontiers 4, no. 7 (2017): 1367–71. http://dx.doi.org/10.1039/c7qo00218a.

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43

Abularrage, Nile S., Brian J. Levandowski, and Ronald T. Raines. "Synthesis and Diels–Alder Reactivity of 4-Fluoro-4-Methyl-4H-Pyrazoles." International Journal of Molecular Sciences 21, no. 11 (2020): 3964. http://dx.doi.org/10.3390/ijms21113964.

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4H-Pyrazoles are emerging scaffolds for “click” chemistry. Late-stage fluorination with Selectfluor® is found to provide a reliable route to 4-fluoro-4-methyl-4H-pyrazoles. 4-Fluoro-4-methyl-3,5-diphenyl-4H-pyrazole (MFP) manifested 7-fold lower Diels–Alder reactivity than did 4,4-difluoro-3,5-diphenyl-4H-pyrazole (DFP), but higher stability in the presence of biological nucleophiles. Calculations indicate that a large decrease in the hyperconjugative antiaromaticity in MFP relative to DFP does not lead to a large loss in Diels–Alder reactivity because the ground-state structure of MFP avoids

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44

M., K. A. IBRAHIM, H. H. ELGHANDOUR A., ABOU-HADEED K., and S. ABDELHAFIZ I. "Utility of Hydrazidoyl Chlorides : Synthesis of New Pyrazoles, Pyrazolo[ 3,4-d]pyridazines, Pyrazolo[4,5-b]pyridines and Pyrazolo[ 4,5-d]pyrimidine Derivatives." Journal of Indian Chemical Society Vol. 69, Jul 1992 (1992): 378–80. https://doi.org/10.5281/zenodo.6004337.

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Chemistry Department, Faculty of Science, Cairo University, Giza, Egypt Chemistry Department, Faculty of Science. Suez-Canal University, Ismalia, Egypt <em>Manuscript received 28 October 1991 revised 26 May 1992, accepted 3 June 1992</em> Hydrazidoyl chlorides (1) were reacted with a variety of active methylene compounds and arylidemnialononitriles .1 medium, to produce polyfunctionally substituted pyrazole derivatives (2-6 and 10). The pyrazoles (2, 3, 6 and 10) were converted into the corresponding pyrazolo[3, 4-<em>d</em>]pyridazine derivatives (7 - 9 and 14), respectively. The aminopyraiol

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45

Shailendra, Jain. "SYNTHESIS OF SOME BENZIMIDAZOLYL PYRAZOLE DERIVATIVES UNDER MICROWAVE IRRADIATION AND THEIR ANTIMICROBIAL ACTIVITIES." GLOBAL JOURNAL OF ENGINEERING SCIENCE AND RESEARCHES 5, no. 6 (2018): 85–89. https://doi.org/10.5281/zenodo.1285780.

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A simple competent method has been developed for the synthesis of some pyrazole derivatives under microwave irradiation. The reaction of benzimidazolyl chalcone (1) with bromine in chloroform gave corresponding dibromochalcones (2), which when condensed with hydrazine hydrate  afforded the title compounds 3-benzimidazolyl-5-aryl-2-pyrazoles (3). All the synthesized compounds were characterized by elemental analysis, IR, NMR and MS spectra. Microwave irradiation method provided improved product yield in a very short span of time. Newly synthesized pyrazoles were screened for their antimicr

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46

Correia, Catarina M., Artur M. S. Silva, and Vera L. M. Silva. "The Role of Flow Chemistry on the Synthesis of Pyrazoles, Pyrazolines and Pyrazole-Fused Scaffolds." Molecules 30, no. 7 (2025): 1582. https://doi.org/10.3390/molecules30071582.

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Nitrogen-containing heterocycles are fundamental scaffolds in organic chemistry, particularly due to their prevalence in pharmaceuticals, agrochemicals and materials science. Among them, five-membered rings, containing two nitrogen atoms in adjacent positions—such as pyrazoles, pyrazolines and indazoles—are especially significant due to their versatile biological activities and structural properties, which led to the search for greener, faster and more efficient methods for their synthesis. Conventional batch synthesis methods, while effective, often face challenges related to reaction efficie

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da Silva, Michael J. V., Raí G. M. Silva, Ulisses Z. Melo та ін. "Theoretical and experimental investigation of the polyeletrophilic β-enamino diketone: straightforward and highly regioselective synthesis of 1,4,5-trisubstituted pyrazoles and pyrazolo[3,4-d]pyridazinones". RSC Advances 6, № 1 (2016): 290–302. http://dx.doi.org/10.1039/c5ra12968k.

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A highly efficient regioselective synthesis of 1,4,5-trisubstituted pyrazoles and pyrazolo[3,4-d]pyridazinones from enamino diketone along with a theoretical and experimental study of the chemical reactivity enamino diketone.

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48

Ebenezer, Oluwakemi, Michael Shapi, and Jack A. Tuszynski. "A Review of the Recent Development in the Synthesis and Biological Evaluations of Pyrazole Derivatives." Biomedicines 10, no. 5 (2022): 1124. http://dx.doi.org/10.3390/biomedicines10051124.

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Pyrazoles are five-membered heterocyclic compounds that contain nitrogen. They are an important class of compounds for drug development; thus, they have attracted much attention. In the meantime, pyrazole derivatives have been synthesized as target structures and have demonstrated numerous biological activities such as antituberculosis, antimicrobial, antifungal, and anti-inflammatory. This review summarizes the results of published research on pyrazole derivatives synthesis and biological activities. The published research works on pyrazole derivatives synthesis and biological activities betw

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Wu, Jialiang, Haofeng Shi, Xuemin Li, et al. "Synthesis of 4-functionalized pyrazoles via oxidative thio- or selenocyanation mediated by PhICl₂ and NH₄SCN/KSeCN." Beilstein Journal of Organic Chemistry 20 (June 28, 2024): 1453–61. http://dx.doi.org/10.3762/bjoc.20.128.

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A series of 4-thio/seleno-cyanated pyrazoles was conveniently synthesized from 4-unsubstituted pyrazoles using NH4SCN/KSeCN as thio/selenocyanogen sources and PhICl2 as the hypervalent iodine oxidant. This metal-free approach was postulated to involve the in situ generation of reactive thio/selenocyanogen chloride (Cl–SCN/SeCN) from the reaction of PhICl2 and NH4SCN/KSeCN, followed by an electrophilic thio/selenocyanation of the pyrazole skeleton.

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50

Wiethan, Carson, Steffany Z. Franceschini, Helio G. Bonacorso, and Mark Stradiotto. "Synthesis of pyrazolo[1,5-a]quinoxalin-4(5H)-ones via one-pot amidation/N-arylation reactions under transition metal-free conditions." Organic & Biomolecular Chemistry 14, no. 37 (2016): 8721–27. http://dx.doi.org/10.1039/c6ob01407k.

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An efficient one-pot procedure for the synthesis of new pyrazolo[1,5-a]quinoxalin-4(5H)-ones from easily prepared 1-(2-chlorophenyl-5-ethylcarboxylate)pyrazoles and various primary alkylamines is described.

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