{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,13]],"date-time":"2026-02-13T04:49:25Z","timestamp":1770958165829,"version":"3.50.1"},"reference-count":77,"publisher":"MDPI AG","issue":"11","license":[{"start":{"date-parts":[[2022,5,29]],"date-time":"2022-05-29T00:00:00Z","timestamp":1653782400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"University of Aveiro, Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia, FCT\/MEC","award":["UIDB\/50006\/2020"],"award-info":[{"award-number":["UIDB\/50006\/2020"]}]},{"name":"University of Aveiro, Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia, FCT\/MEC","award":["CEECINST\/00026\/2018"],"award-info":[{"award-number":["CEECINST\/00026\/2018"]}]},{"name":"Scientific Employment Stimulus\u2014Institutional Call\u2014reference","award":["UIDB\/50006\/2020"],"award-info":[{"award-number":["UIDB\/50006\/2020"]}]},{"name":"Scientific Employment Stimulus\u2014Institutional Call\u2014reference","award":["CEECINST\/00026\/2018"],"award-info":[{"award-number":["CEECINST\/00026\/2018"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Vinylpyrazoles, also known as pyrazolyl olefins, are interesting motifs in organic chemistry but have been overlooked. This review describes the properties and synthetic routes of vinylpyrazoles and highlights their versatility as building blocks for the construction of more complex organic molecules. Concerning the reactivity of vinylpyrazoles, the topics surveyed herein include their use in cycloaddition reactions, free-radical polymerizations, halogenation and hydrohalogenation reactions, and more recently in transition-metal-catalyzed reactions, among other transformations. The current state of the art about vinylpyrazoles is presented with an eye to future developments regarding the chemistry of these interesting compounds. Styrylpyrazoles were not considered in this review, as they were the subject of a previous review article published in 2020.<\/jats:p>","DOI":"10.3390\/molecules27113493","type":"journal-article","created":{"date-parts":[[2022,5,29]],"date-time":"2022-05-29T23:43:03Z","timestamp":1653867783000},"page":"3493","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":8,"title":["Revisiting the Chemistry of Vinylpyrazoles: Properties, Synthesis, and Reactivity"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0938-5085","authenticated-orcid":false,"given":"Vera L. M.","family":"Silva","sequence":"first","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2861-8286","authenticated-orcid":false,"given":"Artur M. S.","family":"Silva","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2022,5,29]]},"reference":[{"key":"ref_1","first-page":"233","article-title":"A review of recent progress (2002\u20132012) on the biological activities of pyrazoles","volume":"2014","author":"Goya","year":"2014","journal-title":"Arkivoc"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"786","DOI":"10.1016\/j.ejmech.2014.11.059","article-title":"Recent advances in bioactive pyrazoles","volume":"97","author":"Senkardes","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"292","DOI":"10.4172\/2161-0444.1000359","article-title":"Pyrazole derivatives with NCN junction and their biological activity: A review","volume":"6","author":"Abrigach","year":"2016","journal-title":"Med. Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"5891","DOI":"10.1016\/j.bmc.2017.09.035","article-title":"Recently reported biological activities of pyrazole compounds","volume":"25","author":"Faria","year":"2017","journal-title":"Bioorg. Med. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"16","DOI":"10.1039\/C6NJ03181A","article-title":"Biologically active pyrazole derivatives","volume":"41","author":"Ansari","year":"2017","journal-title":"New J. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"394","DOI":"10.1016\/j.ejmech.2018.07.007","article-title":"Current progress on antioxidants incorporating the pyrazole core","volume":"156","author":"Silva","year":"2018","journal-title":"Eur. J. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Gomes, P.M.O., Silva, A.M.S., and Silva, V.L.M. (2020). Pyrazoles as key scaffolds for the development of fluorine-18-labeled radiotracers for positron emission tomography (PET). Molecules, 25.","DOI":"10.3390\/molecules25071722"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"5114","DOI":"10.2174\/092986711797636090","article-title":"The state of the art of pyrazole derivatives as monoamine oxidase inhibitors and antidepressant\/anticonvulsant agents","volume":"18","author":"Secci","year":"2011","journal-title":"Curr. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"797","DOI":"10.1007\/s00706-007-0676-4","article-title":"Synthesis and pharmacological evaluation of chlorinated N-alkyl-3 and -5-(2-hydroxyphenyl)pyrazoles as CB1 cannabinoid ligands","volume":"138","author":"Silva","year":"2007","journal-title":"Monatsh. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"226","DOI":"10.3998\/ark.5550190.0011.a19","article-title":"Synthesis and pharmacological evaluation of new (E)- and (Z)-3-aryl-4-styryl-1H-pyrazoles as potential cannabinoid ligands","volume":"2010","author":"Silva","year":"2010","journal-title":"Arkivoc"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"7","DOI":"10.1080\/2164232X.2013.873992","article-title":"Ru(II) trithiacyclononane 5-(2-hydroxyphenyl)-3-[(4-methoxystyryl)pyrazole], a complex with facile synthesis and high cytotoxicity against PC-3 and MDA-MB-231 cells","volume":"1","author":"Marques","year":"2014","journal-title":"Complex Met."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"45","DOI":"10.14233\/ajchem.2019.21455","article-title":"Development of 5-(aryl)-3-phenyl-1H-pyrazole derivatives as potent antimicrobial compounds","volume":"31","author":"Chowdary","year":"2019","journal-title":"Asian J. Chem."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"8299","DOI":"10.1039\/C9NJ01021A","article-title":"Novel styrylpyrazole-glucosides and their dioxolo-bridged doppelgangers: Synthesis and cytotoxicity","volume":"43","author":"Carreira","year":"2019","journal-title":"New J. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1171","DOI":"10.1016\/j.ijbiomac.2021.04.061","article-title":"Pyrazoles as novel protein tyrosine phosphatase 1B (PTP1B) inhibitors: An in vitro and in silico study","volume":"181","author":"Rocha","year":"2021","journal-title":"Int. J. Biol. Macromol."},{"key":"ref_15","doi-asserted-by":"crossref","unstructured":"Rocha, S., Aniceto, N., Guedes, R.C., Albuquerque, H.M.T., Silva, V.L.M., Silva, A.M.S., Corvo, M.L., Fernandes, E., and Freitas, M. (2022). An In Silico and an In Vitro Inhibition Analysis of Glycogen Phosphorylase by Flavonoids, Styrylchromones, and Pyrazoles. Nutrients, 14.","DOI":"10.3390\/nu14020306"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"2","DOI":"10.1016\/j.jfluchem.2012.11.008","article-title":"Synthesis of diversely fluorinated pyrazoles as novel active agrochemical ingredients","volume":"152","author":"Giornal","year":"2013","journal-title":"J. Fluor. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1745","DOI":"10.3987\/COM-91-5773","article-title":"Pyrazoles and isoxazoles derived from 2-hydroxyaryl phenylethynyl ketones: Synthesis and spectrophotometric evaluation of their potential applicability as sunscreens","volume":"32","author":"Garcia","year":"1991","journal-title":"Heterocycles"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"5039","DOI":"10.1021\/ja00039a014","article-title":"New ultraviolet stabilizers: 3- and 5-(2\u2032-hydroxyphenyl)pyrazoles","volume":"114","author":"Catalan","year":"1992","journal-title":"J. Am. Chem. Soc."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2082","DOI":"10.1021\/ol2004947","article-title":"Rapid one-pot, four-step synthesis of highly fluorescent 1,3,4,5-tetrasubstituted pyrazoles","volume":"13","author":"Willy","year":"2011","journal-title":"Org. Lett."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"665","DOI":"10.1002\/anie.197506651","article-title":"Heterocycles as Structural Units in New Optical Brighteners","volume":"14","author":"Dorlars","year":"1975","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1021\/cr60279a003","article-title":"Coordination chemistry of pyrazole-derived ligands","volume":"72","author":"Trofimenko","year":"1972","journal-title":"Chem. Rev."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"237","DOI":"10.1070\/RC1965v034n03ABEH001426","article-title":"Pyrazolone Derivatives as Analytical Reagents","volume":"34","author":"Busev","year":"1965","journal-title":"Russ. Chem. Rev."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2863","DOI":"10.1016\/j.bmcl.2004.03.045","article-title":"Potent DNA gyrase inhibitors; novel 5-vinylpyrazole analogues with Gram-positive antibacterial activity","volume":"14","author":"Tanitame","year":"2004","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_24","first-page":"90","article-title":"An investigation of pyrazoles LVII. Synthesis of 1- and 4-Vinylpyrazoles","volume":"4","author":"Farberov","year":"1959","journal-title":"Khim. Nauka Prom."},{"key":"ref_25","first-page":"381","article-title":"An investigation of pyrazoles LVII. Synthesis of 1- and 4-Vinylpyrazoles","volume":"43","author":"Jacobi","year":"1953","journal-title":"Ktmststoffe"},{"key":"ref_26","first-page":"325","article-title":"An investigation of pyrazoles LVII. Synthesis of 1- and 4-Vinylpyrazoles","volume":"4","author":"Grandberg","year":"1968","journal-title":"Khimiya Geterotsiklicheskikh Soedin."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"946","DOI":"10.1007\/BF00608819","article-title":"Spectroscopic evidence of donor-acceptor interactions of 1-ethyl and 1-vinylpyrazoles","volume":"23","author":"Chipanina","year":"1975","journal-title":"J. Appl. Spectrosc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"922","DOI":"10.1007\/BF01142776","article-title":"NMR spectra and structure of 1-vinylpyrazoles","volume":"34","author":"Voronov","year":"1985","journal-title":"Russ. Chem. Bull."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"917","DOI":"10.1007\/BF01142775","article-title":"NMR and IR spectroscopic study of the structure of quaternary salts of 1-vinylpyrazoles","volume":"34","author":"Voronov","year":"1985","journal-title":"Russ. Chem. Bull."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1007\/BF00957426","article-title":"Quantum-chemical investigation of the electronic structure and geometry of 1-vinylpyrazole derivatives","volume":"37","author":"Danovich","year":"1988","journal-title":"Russ. Chem. Bull."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"180","DOI":"10.1007\/BF00953877","article-title":"Direct 13C-1H coupling constants in the vinyl group of 1-vinylpyrazoles","volume":"36","author":"Afonin","year":"1987","journal-title":"Russ. Chem. Bull."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"639","DOI":"10.1007\/BF00748844","article-title":"Conformational structure of 1-vinylpyrazoles from photoelectron and electron spectroscopic data","volume":"29","author":"Turchaninov","year":"1988","journal-title":"J. Struct. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1121","DOI":"10.1007\/BF00472182","article-title":"Rotational isomerism in 1-vinylpyrazoles and 1-vinylimidazoles from 1H and 13C NMR data and quantum-chemical calculations","volume":"26","author":"Afonin","year":"1990","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1007\/BF00472283","article-title":"15N NMR spectra and specific intramolecular interactions in N-vinylazoles","volume":"27","author":"Afonin","year":"1991","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1838","DOI":"10.1007\/BF00960413","article-title":"Analysis of influence of the 5-methyl group on internal rotation of the vinyl group in 1-vinylpyrazoles by the AM-I method","volume":"40","author":"Afonin","year":"1991","journal-title":"Russ. Chem. Bull."},{"key":"ref_36","unstructured":"Jones, N.O. (1962). Chem. Abstr., 6T, 1077h. (British Patent 887, 365)."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"797","DOI":"10.1007\/BF00486965","article-title":"Studies on pyrazoles LX. Synthesis of N-Vinylpyrazoles","volume":"4","author":"Grandberg","year":"1968","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"3459","DOI":"10.1021\/jo00835a061","article-title":"Vinylpyrazoles","volume":"35","author":"Trofimenko","year":"1970","journal-title":"J. Org. Chem."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1248\/yakushi1947.98.2_165","article-title":"Studies of Heterocyclic Compounds. XVI. Synthesis of 1-Vinylpyrazoles by Dehydrohalogenation of 1-(2-Haloethyl)pyrazoles","volume":"98","author":"Ochi","year":"1978","journal-title":"Yakugaku Zasshi J. Pharm. Soc. Jpn."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"452","DOI":"10.1007\/s10593-005-0170-z","article-title":"Synthesis of N-Vinylpyrazoles","volume":"41","author":"Attarian","year":"2005","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1016\/j.tet.2006.10.009","article-title":"The N-vinyl group as a protection group of the preparation of 3(5)-substituted pyrazoles via bromine\u2013lithium exchange","volume":"63","author":"Iddon","year":"2007","journal-title":"Tetrahedron"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"305","DOI":"10.1016\/S0040-4039(00)93716-X","article-title":"The thermal and photochemical reactions of 3H-1,2-diazepines: A new variation on the diazepine-pyrazole rearrangement","volume":"17","author":"Anderson","year":"1976","journal-title":"Tetrahedron Lett."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1002\/pol.1975.170130214","article-title":"Preparation of New Heterocyclic Monomers: Vinylisoxazoles, Vinylpyrazoles, and Vinylpyrazolones","volume":"13","author":"Ponticello","year":"1975","journal-title":"J. Polym. Sci. A Polym. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"4957","DOI":"10.1016\/j.tet.2014.05.005","article-title":"From N-sulfonyl,C-homoallyl-hydrazones to pyrazole and pyridazine (N2)-heterocycles: The ultimate aromatization process","volume":"70","author":"Mboyi","year":"2014","journal-title":"Tetrahedron"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1492","DOI":"10.1039\/C4OB02365J","article-title":"Domino reaction involving the Bestmann\u2013Ohira reagent and \u03b1,\u03b2-unsaturated aldehydes: Efficient synthesis of functionalized pyrazoles","volume":"13","author":"Ahamad","year":"2015","journal-title":"Org. Biomol. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"3967","DOI":"10.1039\/jr9630003967","article-title":"An Investigation of pyrazoles LVII. Synthesis of 1- and 4-vinylpyrazoles","volume":"4","author":"Finar","year":"1963","journal-title":"J. Chem. Soc."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1007\/BF00601139","article-title":"An investigation of pyrazoles","volume":"4","author":"Grandberg","year":"1970","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1373","DOI":"10.1002\/jhet.5570090632","article-title":"Pyrazoles XI. The synthesis of 1,1\u2032-dimethylbipyrazolyls","volume":"9","author":"Timmermans","year":"1972","journal-title":"J. Heterocycl. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1297","DOI":"10.1039\/p19780001297","article-title":"Polyaza-azulenes. Part 1. Synthesis and Reactions of Some 2,3,3a,6-Tetrahydropyrazolo[3,4-d][1,2]diazepines","volume":"11","author":"Frost","year":"1978","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"6683","DOI":"10.1016\/S0040-4020(01)82108-6","article-title":"New cycloaddition reactions of 1-phenyl-4-vinylpyrazole","volume":"42","year":"1986","journal-title":"Tetrahedron"},{"key":"ref_51","doi-asserted-by":"crossref","unstructured":"Sim\u00f3n, M.M., Laviada, M.J.A., and Sep\u00falveda Arques, J. (1990). Cycloadditions with 1-phenyl-5-vinylpyrazole. J. Chem. Soc. Perkin Trans. 1, 2749\u20132750.","DOI":"10.1039\/P19900002749"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"9237","DOI":"10.1016\/0040-4020(96)00473-5","article-title":"Diels-Alder Cycloaddition of Vinyipyrazoles. Synergy between Microwave Irradiation and Solvent-Free Conditions","volume":"52","author":"Carrillo","year":"1996","journal-title":"Tetrahedron"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1039\/b003752o","article-title":"Microwave irradiation in solvent-free conditions: An eco-friendly methodology to prepare indazoles, pyrazolopyridines and bipyrazoles by cycloaddition reactions","volume":"2","author":"Langa","year":"2000","journal-title":"Green Chem."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1113","DOI":"10.1007\/BF00809294","article-title":"Cycloaddition Reactions of 1-tert-Butyl-4-vinylpyrazole","volume":"120","year":"1989","journal-title":"Monatsh. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"626","DOI":"10.1134\/S1070363208040191","article-title":"Diels\u2013Alder Reactions of 3- and 5-Methyl-1-vinylpyrazoles with Cyclohexa-1,3-diene and Hydrogenation of the Reaction Products","volume":"78","author":"Attaryana","year":"2008","journal-title":"Russ. J. Gen. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"768","DOI":"10.1007\/BF00472748","article-title":"Reaction of 1-vinylpyrazoles with tetracyanoethylene","volume":"25","author":"Petrova","year":"1989","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1007\/BF00697102","article-title":"The reactivity of 3-methyl- and 5-methyl-l-vinylpyrazoles in free-radical polymerization","volume":"42","author":"Nikitenko","year":"1993","journal-title":"Russ. Chem. Bull."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"774","DOI":"10.1007\/BF00471650","article-title":"Bromination of 1-vinylpyrazoles","volume":"14","author":"Domnina","year":"1978","journal-title":"Chem. Heterocycl. Compd."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"2359","DOI":"10.1007\/BF00956800","article-title":"Hydrohalogenation of 1-vinylpyrazoles","volume":"34","author":"Voronov","year":"1985","journal-title":"Russ. Chem. Bull."},{"key":"ref_60","unstructured":"Marcin, L.R., Higgins, M.A., Bronson, J.J., Zusi, F.C., Macor, J.E., and Ding, M. (2015). Triazolopyridine ether derivatives and their use in neurological and psychiatric disorders. (WO 2015\/042243)."},{"key":"ref_61","unstructured":"Giovannini, R., Bertani, B., Ferrara, M., Lingard, I., Mazzaferro, R., and Rosenbrock, H. (2013). Phenyl-3-aza-bicyclo[3.1.0]hex-3-yl-methanones and the use thereof as medicament. (WO2013\/17657)."},{"key":"ref_62","unstructured":"Lim, J., Kelley, E.H., Methot, J.L., Zhou, H., Petrocchi, A., Mansoor, U.F., Fischer, C., O\u2019Boyle, B.M., Guerin, D.J., and Bienstock, E. (2013). Novel compounds that are ERK inhibitors. (WO 2013\/063214)."},{"key":"ref_63","unstructured":"Dilger, A.K., Corte, J.R., De Lucca, I., Fang, T., Yang, W., Wang, Y., Pabbisetty, K.B., Ewing, W.R., Zhu, Y., and Wexler, R.R. (2015). Macrocyclic factor xia inhibitors condensed with heterocycles. (WO 2015\/116882)."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"4311","DOI":"10.1002\/ejoc.201900123","article-title":"N-Difluorocyclopropyl-Substituted Pyrazoles: Synthesis and Reactivity","volume":"2019","author":"Nosik","year":"2019","journal-title":"Eur. J. Org. Chem."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1002\/mrc.2854","article-title":"The effects of intramolecular and intermolecular coordination on 31P nuclear shielding: Phosphorylated azoles","volume":"50","author":"Chernyshev","year":"2012","journal-title":"Magn. Reson. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"4927","DOI":"10.1016\/S0040-4039(03)01037-2","article-title":"Copper-promoted\/catalyzed C-N and C-O bond cross-coupling with vinylboronic acid and its utilities","volume":"44","author":"Lam","year":"2003","journal-title":"Tetrahedron Lett."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"953","DOI":"10.1021\/ol990909q","article-title":"Synthesis and Activity of a New Generation of Ruthenium-Based Olefin Metathesis Catalysts Coordinated with 1,3-Dimesityl-4,5-dihydroimidazol-2-ylidene Ligands","volume":"1","author":"Scholl","year":"1999","journal-title":"Org. Lett."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"2039","DOI":"10.1002\/anie.199520391","article-title":"A Series of Well-Defined Metathesis Catalysts\u2013Synthesis of [RuCl2(=CHR\u2032)(PR3)2] and Its Reactions","volume":"34","author":"Schwab","year":"1995","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"100","DOI":"10.1021\/ja952676d","article-title":"Synthesis and Applications of RuCl2(=CHR\u2018)(PR3)2:\u2009 The Influence of the Alkylidene Moiety on Metathesis Activity","volume":"118","author":"Schwab","year":"1996","journal-title":"J. Am. Chem. Soc."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"8168","DOI":"10.1021\/ja001179g","article-title":"Efficient and Recyclable Monomeric and Dendritic Ru-Based Metathesis Catalysts","volume":"122","author":"Garber","year":"2000","journal-title":"J. Am. Chem. Soc."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"1173","DOI":"10.1039\/b606984n","article-title":"Direct transition metal-catalyzed functionalization of heteroaromatic compounds","volume":"36","author":"Seregin","year":"2007","journal-title":"Chem. Soc. Rev."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"624","DOI":"10.1021\/cr900005n","article-title":"Rhodium-Catalyzed C\u2212C Bond Formation via Heteroatom-Directed C\u2212H Bond Activation","volume":"110","author":"Colby","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"4244","DOI":"10.1021\/cs501366q","article-title":"Rhodium(I)-N-Heterocyclic Carbene Catalyst for Selective Coupling of N-Vinylpyrazoles with Alkynes via C-H Activation","volume":"4","author":"Passarelli","year":"2014","journal-title":"ACS Catal."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"9623","DOI":"10.1016\/S0040-4020(99)00508-6","article-title":"The Effect of Focused Microwaves on the Reaction of Ethyl N-Trichloroethylidenecarbamate with Pyrazole Derivatives","volume":"55","author":"Carrillo","year":"1999","journal-title":"Tetrahedron"},{"key":"ref_75","doi-asserted-by":"crossref","unstructured":"Ameta, K.L., Kant, R., Penoni, A., Maspero, A., and Scapinello, L. (2022). Sulfur-Containing Pyrazoles, Pyrazolines and Indazoles. N-Heterocycles, Springer.","DOI":"10.1007\/978-981-19-0832-3"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1462","DOI":"10.1007\/BF00864347","article-title":"Interaction of 1-vinylpyrazoles with alkanethiols","volume":"41","author":"Erushnikova","year":"1992","journal-title":"Russ. Chem. Bull."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"144","DOI":"10.1134\/S1070428017010298","article-title":"Directed Synthesis of 3-(2,2-Dichlorocyclopropyl)pyrazoles","volume":"53","author":"Kobelevskaya","year":"2017","journal-title":"Russ. J. Org. 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