Efficient synthesis of 1,3-diaryl-4-halo-1H-pyrazoles from 3-arylsydnones and 2-aryl-1,1-dihalo-1-alkenes

Scholarly Works

• Jadav, J. P.; Vankar, J. K.; Gupta, A.; Gururaja, G. N. Atmospheric Oxygen Facilitated Oxidative Amidation to α-Ketoamides and Unusual One Carbon Degradative Amidation to N-Alkyl Amides. The Journal of organic chemistry 2023, 88, 15551–15561. doi:10.1021/acs.joc.3c00457
• Zerbib, S.; Khouili, M.; Catto, M.; Bouissane, L. Sydnone: Synthesis, Reactivity and Biological Activities. Current medicinal chemistry 2023, 30, 1122–1144. doi:10.2174/0929867329666220620123050
• El-Naggar, M. A.; Albering, J. H.; Barakat, A.; Abu-Youssef, M. A.; Soliman, S. M.; Badr, A. M. New bioactive 1D Ag(I) coordination polymers with pyrazole and triazine ligands; Synthesis, X-ray structure, Hirshfeld analysis and DFT studies. Inorganica Chimica Acta 2022, 537, 120948. doi:10.1016/j.ica.2022.120948
• Konwar, M.; Hazarika, R.; Sarma, D. Synthetic advances in C(sp2)-H/N–H arylation of pyrazole derivatives through activation/substitution. Tetrahedron 2021, 102, 132504. doi:10.1016/j.tet.2021.132504
• Grošelj, U.; Svete, J. Organic Reactions - [3 + 2] Cycloadditions of Azomethine Imines. Organic Reactions 2020, 529–930. doi:10.1002/0471264180.or103.02
• Samir, B.; Kalalian, C.; Roth, E.; Salghi, R.; Chakir, A. Gas-phase UV absorption spectra of pyrazine, pyrimidine and pyridazine. Chemical Physics Letters 2020, 751, 137469. doi:10.1016/j.cplett.2020.137469
• Kaur, G.; Utreja, D.; Jain, N.; Dhillon, N. K. Synthesis and Evaluation of Pyrazole Derivatives as Potent Antinemic Agents. Russian Journal of Organic Chemistry 2020, 56, 113–118. doi:10.1134/s1070428020010182
• Cherepanov, I. A.; Moiseev, S. K. Recent developments in the chemistry of sydnones and sydnone imines. Advances in Heterocyclic Chemistry; Elsevier, 2020; Vol. 131, pp 49–164. doi:10.1016/bs.aihch.2019.11.003
• Channar, P. A.; Saeed, A.; Erben, M. F.; Larik, F. A.; Riaz, S.; Flörke, U.; Arshad, M. Synthesis, conformational studies and NBO analysis of (4-chloro-3,5-dimethyl-1H-pyrazol- 1-yl)(p-tolyl)methanone. Journal of Molecular Structure 2019, 1191, 152–157. doi:10.1016/j.molstruc.2019.04.085
• Samir, B.; Kalalian, C.; Roth, E.; Salghi, R.; Chakir, A. Gas-phase UV absorption spectra and OH-oxidation kinetics of 1H-1,2,3-triazole and pyrazole. RSC advances 2019, 9, 27361–27368. doi:10.1039/c9ra04235k
• Maddali, L. N. R.; Meka, S. Cross-coupling reactivity of 1,1-dichloroalkenes under palladium catalysis: domino synthesis of diarylalkynes. New Journal of Chemistry 2018, 42, 4412–4418. doi:10.1039/c7nj05107g
• Vernier, W. F.; Gomez, L. Regioselective palladium-catalyzed CH arylation of 4-alkoxy and 4-thioalkyl pyrazoles. Tetrahedron Letters 2017, 58, 4587–4590. doi:10.1016/j.tetlet.2017.10.047
• Ziadi, A.; Uchida, N.; Kato, H.; Hisamatsu, R.; Sato, A.; Hagihara, S.; Itami, K.; Torii, K. U. Discovery of synthetic small molecules that enhance the number of stomata: C-H functionalization chemistry for plant biology. Chemical communications (Cambridge, England) 2017, 53, 9632–9635. doi:10.1039/c7cc04526c
• Belkessam, F.; Aidene, M.; Soulé, J.-F.; Doucet, H. Direct C3‐Arylation of 2 H‐Indazole Derivatives with Aryl Bromides by using Low Loading of a Phosphine‐free Palladium Catalyst. ChemCatChem 2017, 9, 2239–2249. doi:10.1002/cctc.201601420
• Brahim, M.; Ammar, H. B.; Soulé, J.-F.; Doucet, H. Reactivity of 1-(2-bromobenzyl)-4-halopyrazoles in intermolecular and intramolecular Pd-catalysed direct arylations. Tetrahedron 2016, 72, 4312–4320. doi:10.1016/j.tet.2016.05.079
• Morita, T.; Kobayashi, D.; Matsumura, K.; Johmoto, K.; Uekusa, H.; Fuse, S.; Takahashi, T. Sequential S(N)Ar Reaction/Suzuki-Miyaura Coupling/C-H Direct Arylations Approach for the Rapid Synthesis of Tetraaryl-Substituted Pyrazoles. Chemistry, an Asian journal 2015, 10, 1626–1630. doi:10.1002/asia.201500362
• Guo, H.-M.; Zhao, P.-S.; Wu, Q.; Li, Y.-F. Synthesis, Crystal Structure, Spectra and Quantum Chemical Study on 1-Phenyl-3-(4-nitrophenyl)-5-(2-thienyl)-2-pyrazoline. Molecules (Basel, Switzerland) 2014, 19, 5313–5324. doi:10.3390/molecules19045313
• Takfaoui, A.; Zhao, L.; Touzani, R.; Dixneuf, P. H.; Doucet, H. Palladium-catalysed direct diarylations of pyrazoles with aryl bromides: a one step access to 4,5-diarylpyrazoles. Tetrahedron Letters 2014, 55, 1697–1701. doi:10.1016/j.tetlet.2014.01.079
• Smari, I.; Youssef, C.; Yuan, K.; Beladhria, A.; Ammar, H. B.; Hassine, B. B.; Doucet, H. Formyl Substituent at C-4 of Pyrazoles: A Temporary Protecting Group for Regioselective Palladium-Catalyzed Direct Arylation at C-5. European Journal of Organic Chemistry 2014, 2014, 1778–1786. doi:10.1002/ejoc.201301593
• Kumar, K. A.; Jayaroopa, P.

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