Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method

The 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 c...

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Autores:
Trilleras, Jorge
Tipo de recurso:
Fecha de publicación:
2022
Institución:
Universidad del Atlántico
Repositorio:
Repositorio Uniatlantico
Idioma:
eng
OAI Identifier:
oai:repositorio.uniatlantico.edu.co:20.500.12834/843
Acceso en línea:
https://hdl.handle.net/20.500.12834/843
https://www.scopus.com/record/display.uri?eid=2-s2.0-85124887565&doi=10.3390%2fM1341&origin=inward&txGid=5618b897dc3d8c383a4dd756255f557e
Palabra clave:
3,4-substituted pyrrole synthesis
TosMIC
Van Leusen reaction
Rights
openAccess
License
http://creativecommons.org/licenses/by-nc/4.0/
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oai_identifier_str oai:repositorio.uniatlantico.edu.co:20.500.12834/843
network_acronym_str UNIATLANT2
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dc.title.spa.fl_str_mv Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
title Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
spellingShingle Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
3,4-substituted pyrrole synthesis
TosMIC
Van Leusen reaction
title_short Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
title_full Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
title_fullStr Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
title_full_unstemmed Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
title_sort Synthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen Method
dc.creator.fl_str_mv Trilleras, Jorge
dc.contributor.author.none.fl_str_mv Trilleras, Jorge
dc.contributor.other.none.fl_str_mv Quiroga, Jairo
Hormaza, Angelina
dc.subject.keywords.spa.fl_str_mv 3,4-substituted pyrrole synthesis
TosMIC
Van Leusen reaction
topic 3,4-substituted pyrrole synthesis
TosMIC
Van Leusen reaction
description The 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.
publishDate 2022
dc.date.accessioned.none.fl_str_mv 2022-11-15T19:43:29Z
dc.date.available.none.fl_str_mv 2022-11-15T19:43:29Z
dc.date.issued.none.fl_str_mv 2022-02-15
dc.date.submitted.none.fl_str_mv 2022-01-08
dc.type.coarversion.fl_str_mv http://purl.org/coar/version/c_970fb48d4fbd8a85
dc.type.coar.fl_str_mv http://purl.org/coar/resource_type/c_2df8fbb1
dc.type.driver.spa.fl_str_mv info:eu-repo/semantics/article
dc.type.hasVersion.spa.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.spa.spa.fl_str_mv Artículo
status_str publishedVersion
dc.identifier.citation.spa.fl_str_mv Trilleras, 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/M1341
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/20.500.12834/843
dc.identifier.doi.none.fl_str_mv 10.3390/M1341
dc.identifier.instname.spa.fl_str_mv Universidad del Atlántico
dc.identifier.reponame.spa.fl_str_mv Repositorio Universidad del Atlántico
dc.identifier.url.none.fl_str_mv https://www.scopus.com/record/display.uri?eid=2-s2.0-85124887565&doi=10.3390%2fM1341&origin=inward&txGid=5618b897dc3d8c383a4dd756255f557e
identifier_str_mv Trilleras, 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/M1341
10.3390/M1341
Universidad del Atlántico
Repositorio Universidad del Atlántico
url https://hdl.handle.net/20.500.12834/843
https://www.scopus.com/record/display.uri?eid=2-s2.0-85124887565&doi=10.3390%2fM1341&origin=inward&txGid=5618b897dc3d8c383a4dd756255f557e
dc.language.iso.spa.fl_str_mv eng
language eng
dc.rights.coar.fl_str_mv http://purl.org/coar/access_right/c_abf2
dc.rights.uri.*.fl_str_mv http://creativecommons.org/licenses/by-nc/4.0/
dc.rights.cc.*.fl_str_mv Attribution-NonCommercial 4.0 International
dc.rights.accessRights.spa.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by-nc/4.0/
Attribution-NonCommercial 4.0 International
http://purl.org/coar/access_right/c_abf2
eu_rights_str_mv openAccess
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.publisher.place.spa.fl_str_mv Barranquilla
dc.publisher.sede.spa.fl_str_mv Sede Norte
dc.source.spa.fl_str_mv Molbank
institution Universidad del Atlántico
bitstream.url.fl_str_mv https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/843/1/molbank-2022-M1341.pdf
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spelling Trilleras, Jorge63cd720d-db33-4820-979b-79c2fad74271Quiroga, JairoHormaza, Angelina2022-11-15T19:43:29Z2022-11-15T19:43:29Z2022-02-152022-01-08Trilleras, 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/M1341https://hdl.handle.net/20.500.12834/84310.3390/M1341Universidad del AtlánticoRepositorio Universidad del Atlánticohttps://www.scopus.com/record/display.uri?eid=2-s2.0-85124887565&doi=10.3390%2fM1341&origin=inward&txGid=5618b897dc3d8c383a4dd756255f557eThe 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.application/pdfenghttp://creativecommons.org/licenses/by-nc/4.0/Attribution-NonCommercial 4.0 Internationalinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2MolbankSynthesis of 3-Aroyl-4-heteroarylpyrrole Derivatives by the Van Leusen MethodPúblico general3,4-substituted pyrrole synthesisTosMICVan Leusen reactioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionArtículohttp://purl.org/coar/version/c_970fb48d4fbd8a85http://purl.org/coar/resource_type/c_2df8fbb1BarranquillaSede NortePetri, 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]Wang, 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]Zhan, 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]Domagala, 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]Bhardwaj, 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]Philkhana, S.C.; Badmus, F.O.; Dos Reis, I.C.; Kartika, R. Recent Advancements in Pyrrole Synthesis. Synthesis 2021, 53, 1531–1555. [CrossRef] [PubMed]Taghi 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]Kumar, K. TosMIC: A Powerful Synthon for Cyclization and Sulfonylation. ChemistrySelect 2020, 5, 10298–10328. [CrossRef]Farooq, S.; Ngaini, Z. Recent synthetic methodologies for chalcone synthesis (2013–2018). Curr. Organocatal. 2019, 6, 184–192. [CrossRef]Ardiansah, B. Chalcones bearing N, O, and S-heterocycles: Recent notes on their biological significances. J. Appl. Pharm. Sci. 2019, 9, 117–129. [CrossRef]Manasa, 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]Aitha, 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]Zhan, 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]Quiroga, 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]Trilleras, 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.Van Leusen, D.; Van Leusen, A.M. Synthetic Uses of Tosylmethyl Isocyanide (TosMIC). Org. React. 2001, 57, 417–666. [CrossRef]Van 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]Ma, 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]http://purl.org/coar/resource_type/c_2df8fbb1ORIGINALmolbank-2022-M1341.pdfmolbank-2022-M1341.pdfapplication/pdf951532https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/843/1/molbank-2022-M1341.pdf5e4006e56cb0352dcf85bc1283688628MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8914https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/843/2/license_rdf24013099e9e6abb1575dc6ce0855efd5MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81306https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/843/3/license.txt67e239713705720ef0b79c50b2ececcaMD5320.500.12834/843oai:repositorio.uniatlantico.edu.co:20.500.12834/8432022-11-15 14:43:30.739DSpace de la Universidad de Atlánticosysadmin@mail.uniatlantico.edu.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