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dc.contributor.authorTrilleras, Jorge
dc.contributor.otherQuiroga, Jairo
dc.contributor.otherHormaza, Angelina
dc.date.accessioned2022-11-15T19:43:29Z
dc.date.available2022-11-15T19:43:29Z
dc.date.issued2022-02-15
dc.date.submitted2022-01-08
dc.identifier.citationTrilleras, J.; Quiroga, J.; Hormaza, A. Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method. Molbank 2022, 2022, M1341. https://doi.org/10.3390/M1341spa
dc.identifier.urihttps://hdl.handle.net/20.500.12834/843
dc.description.abstractThe synthesis and structural diversification of N-heterocycles systems have attracted much attention because of their potential applications. Three 6-aryl-3-methyl-1-phenyl-1H-pyrazolo[3,4- b]pyridine-5-carbaldehyde 4 derivatives, in reaction with acetophenones 5, via conventional Claisen– Schmidt condensation reactions, generated the respective enones. The enones were used as electrondeficient olefins in a “formal” [2+3] cycloaddition reaction using p-tosylmethyl isocyanide—TosMIC 7. This protocol allows access to 3-(substituted aroyl)-4-heteroaryl pyrrole derivatives by the Van Leusen method.spa
dc.format.mimetypeapplication/pdfspa
dc.language.isoengspa
dc.rights.urihttp://creativecommons.org/licenses/by-nc/4.0/*
dc.sourceMolbankspa
dc.titleSynthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Methodspa
dcterms.bibliographicCitationPetri, G.L.; Spanò, V.; Spatola, R.; Holl, R.; Raimondi, M.V.; Barraja, P.; Montalbano, A. Bioactive pyrrole-based compounds with target selectivity. Eur. J. Med. Chem. 2020, 208, 112783. [CrossRef]spa
dcterms.bibliographicCitationWang, P.; Nguyen, K.C.; Lindsey, J.S. Synthesis of the Ring C Pyrrole of Native Chlorophylls and Bacteriochlorophylls. J. Org. Chem. 2019, 84, 11286–11293. [CrossRef]spa
dcterms.bibliographicCitationZhan, X.-P.; Lan, L.; Wang, S.; Zhao, K.; Xin, Y.-X.; Qi, Q.; Wang, Y.-L.; Mao, Z.-M. Synthesis and Anticancer Activity of 3-(Substituted Aroyl)-4-(3,4,5-trimethoxyphenyl)-1H-pyrrole Derivatives. Chem. Biodivers. 2017, 14, e1600219. [CrossRef] [PubMed]spa
dcterms.bibliographicCitationDomagala, A.; Jarosz, T.; Lapkowski, M. Living on pyrrolic foundations e Advances in natural and artificial bioactive pyrrole derivatives. Eur. J. Med. Chem. 2015, 100, 176–187. [CrossRef] [PubMed]spa
dcterms.bibliographicCitationBhardwaj, V.; Gumber, D.; Abbot, V.; Dhiman, S.; Sharma, P. Pyrrole: A resourceful small molecule in key medicinal heteroaromatics. RSC Adv. 2015, 5, 15233–15266. [CrossRef]spa
dcterms.bibliographicCitationPhilkhana, S.C.; Badmus, F.O.; Dos Reis, I.C.; Kartika, R. Recent Advancements in Pyrrole Synthesis. Synthesis 2021, 53, 1531–1555. [CrossRef] [PubMed]spa
dcterms.bibliographicCitationTaghi Nazeri, M.; Shaabani, A. Synthesis of polysubstituted pyrroles via isocyanide-based multicomponent reactions as an efficient synthesis tool. New J. Chem. 2021, 45, 21967–22011. [CrossRef]spa
dcterms.bibliographicCitationKumar, K. TosMIC: A Powerful Synthon for Cyclization and Sulfonylation. ChemistrySelect 2020, 5, 10298–10328. [CrossRef]spa
dcterms.bibliographicCitationFarooq, S.; Ngaini, Z. Recent synthetic methodologies for chalcone synthesis (2013–2018). Curr. Organocatal. 2019, 6, 184–192. [CrossRef]spa
dcterms.bibliographicCitationArdiansah, B. Chalcones bearing N, O, and S-heterocycles: Recent notes on their biological significances. J. Appl. Pharm. Sci. 2019, 9, 117–129. [CrossRef]spa
dcterms.bibliographicCitationManasa, K.L.; Visweswara Sastry, K.N.; Tangella, Y.; Babu, B.N. Tandem Synthesis of 3,4-Disubstituted Pyrroles from Aldehydes, 1,3-Diketones and TosMIC Under Metal-Free Conditions. ChemistrySelect 2018, 3, 2730–2733. [CrossRef]spa
dcterms.bibliographicCitationAitha, A.; Payili, N.; Rekula, S.R.; Yennam, S.; Anireddy, J.S. ”One-Pot” Selective Synthesis of 3,4-Disubstituted Pyrroles and Benzo[f ]indole-4,9-diones from 1,3-Indanedione, Aromatic Aldehydes and TosMIC. ChemistrySelect 2017, 2, 7246–7250. [CrossRef]spa
dcterms.bibliographicCitationZhan, X.; Lan, L.; Zhang, Y.; Chen, J.; Zhao, K.; Wang, S.; Xin, Y.; Mao, Z. Synthesis and Cytotoxicity Evaluation of New 3-substituted 4-(4-methyloxyphenyl)-1H-Pyrrole Derivatives. Bull. Korean Chem. Soc. 2016, 37, 200–206. [CrossRef]spa
dcterms.bibliographicCitationQuiroga, J.; Trilleras, J.; Insuasty, B.; Abonía, R.; Nogueras, M.; Cobo, J. Regioselective formylation of pyrazolo[3,4-b]pyridine and pyrazolo[1,5-a]pyrimidine systems using Vilsmeier–Haack conditions. Tetrahedron Lett. 2008, 49, 2689–2691. [CrossRef]spa
dcterms.bibliographicCitationTrilleras, J. Synthesis of ortho-Functionalized Heterocyclic Aldehydes and Study of Their Condensation, Cyclocondensation and SNAr Reaction in the Preparation of , -Unsaturated and Fused Heterocyclic Systems. Ph.D. Thesis, Universidad del Valle, Cali, Colombia, 2009.spa
dcterms.bibliographicCitationVan Leusen, D.; Van Leusen, A.M. Synthetic Uses of Tosylmethyl Isocyanide (TosMIC). Org. React. 2001, 57, 417–666. [CrossRef]spa
dcterms.bibliographicCitationVan Leusen, A.M.; Siderius, H.; Hoogenboom, B.E.; Van Leusen, D. A new and simple synthesis of the pyrrole ring system from Michael acceptors and tosylmethylisocyanides. Tetrahedron Lett. 1972, 13, 5337–5340. [CrossRef]spa
dcterms.bibliographicCitationMa, Z.; Ma, Z.; Zhang, D. Synthesis of Multi-Substituted Pyrrole Derivatives Through [3+2] Cycloaddition with Tosylmethyl Isocyanides (TosMICs) and Electron-Deficient Compounds. Molecules 2018, 23, 2666. [CrossRef] [PubMed]spa
datacite.rightshttp://purl.org/coar/access_right/c_abf2spa
oaire.resourcetypehttp://purl.org/coar/resource_type/c_2df8fbb1spa
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85spa
dc.audiencePúblico generalspa
dc.identifier.doi10.3390/M1341
dc.identifier.instnameUniversidad del Atlánticospa
dc.identifier.reponameRepositorio Universidad del Atlánticospa
dc.identifier.urlhttps://www.scopus.com/record/display.uri?eid=2-s2.0-85124887565&doi=10.3390%2fM1341&origin=inward&txGid=5618b897dc3d8c383a4dd756255f557e
dc.rights.ccAttribution-NonCommercial 4.0 International*
dc.subject.keywords3,4-substituted pyrrole synthesisspa
dc.subject.keywordsTosMICspa
dc.subject.keywordsVan Leusen reactionspa
dc.type.driverinfo:eu-repo/semantics/articlespa
dc.type.hasVersioninfo:eu-repo/semantics/publishedVersionspa
dc.type.spaArtículospa
dc.publisher.placeBarranquillaspa
dc.rights.accessRightsinfo:eu-repo/semantics/openAccessspa
dc.publisher.sedeSede Nortespa


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