SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde

We report the experimental results of unexpected aromatic nucleophilic substitution reaction products on 2-amino-4,6-dichloropyrimidine-5-carbaldehyde. The isolated compounds are products of amination, solvolysis, and condensation processes under mild and environmentally friendly conditions, due to...

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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:20.500.12834/767
Acceso en línea:
https://hdl.handle.net/20.500.12834/767
Palabra clave:
amination
dichloropyrimidines
aromatic substitution
Rights
openAccess
License
http://creativecommons.org/licenses/by-nc/4.0/
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dc.title.spa.fl_str_mv SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde
title SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde
spellingShingle SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde
amination
dichloropyrimidines
aromatic substitution
title_short SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde
title_full SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde
title_fullStr SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde
title_full_unstemmed SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde
title_sort SNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehyde
dc.creator.fl_str_mv Trilleras, Jorge
dc.contributor.author.none.fl_str_mv Trilleras, Jorge
dc.contributor.other.none.fl_str_mv Pérez Gamboa, Alfredo
Quiroga, Jairo
dc.subject.keywords.spa.fl_str_mv amination
dichloropyrimidines
aromatic substitution
topic amination
dichloropyrimidines
aromatic substitution
description We report the experimental results of unexpected aromatic nucleophilic substitution reaction products on 2-amino-4,6-dichloropyrimidine-5-carbaldehyde. The isolated compounds are products of amination, solvolysis, and condensation processes under mild and environmentally friendly conditions, due to the influence of structural factors of the starting pyrimidine and a high concentration of alkoxide ions. This method allows the building of pyrimidine-based compound precursors of N-heterocyclic systems.
publishDate 2022
dc.date.accessioned.none.fl_str_mv 2022-11-15T19:11:22Z
dc.date.available.none.fl_str_mv 2022-11-15T19:11:22Z
dc.date.issued.none.fl_str_mv 2022-08-12
dc.date.submitted.none.fl_str_mv 2022-06-30
dc.type.coarversion.fl_str_mv http://purl.org/coar/version/c_b1a7d7d4d402bcce
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/draft
dc.type.spa.spa.fl_str_mv Artículo
status_str draft
dc.identifier.citation.spa.fl_str_mv Trilleras, J.; Pérez- Gamboa, A.; Quiroga, J. SNAr Reactions on 2-Amino-4,6- dichloropyrimidine-5-carbaldehyde. Molbank 2022, 2022, M1426. https:// doi.org/10.3390/M1426
dc.identifier.uri.none.fl_str_mv https://hdl.handle.net/20.500.12834/767
dc.identifier.doi.none.fl_str_mv 10.3390/M1426
dc.identifier.instname.spa.fl_str_mv Universidad del Atlántico
dc.identifier.reponame.spa.fl_str_mv Repositorio Universidad del Atlántico
identifier_str_mv Trilleras, J.; Pérez- Gamboa, A.; Quiroga, J. SNAr Reactions on 2-Amino-4,6- dichloropyrimidine-5-carbaldehyde. Molbank 2022, 2022, M1426. https:// doi.org/10.3390/M1426
10.3390/M1426
Universidad del Atlántico
Repositorio Universidad del Atlántico
url https://hdl.handle.net/20.500.12834/767
dc.language.iso.spa.fl_str_mv eng
language eng
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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
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eu_rights_str_mv openAccess
dc.format.mimetype.spa.fl_str_mv application/pdf
dc.coverage.spatial.none.fl_str_mv Colombia
dc.publisher.place.spa.fl_str_mv Barranquilla
dc.publisher.discipline.spa.fl_str_mv Ingeniería Química
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/20.500.12834/767/1/molbank-2022-M1426.pdf
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spelling Trilleras, Jorge63cd720d-db33-4820-979b-79c2fad74271Pérez Gamboa, AlfredoQuiroga, JairoColombia2022-11-15T19:11:22Z2022-11-15T19:11:22Z2022-08-122022-06-30Trilleras, J.; Pérez- Gamboa, A.; Quiroga, J. SNAr Reactions on 2-Amino-4,6- dichloropyrimidine-5-carbaldehyde. Molbank 2022, 2022, M1426. https:// doi.org/10.3390/M1426https://hdl.handle.net/20.500.12834/76710.3390/M1426Universidad del AtlánticoRepositorio Universidad del AtlánticoWe report the experimental results of unexpected aromatic nucleophilic substitution reaction products on 2-amino-4,6-dichloropyrimidine-5-carbaldehyde. The isolated compounds are products of amination, solvolysis, and condensation processes under mild and environmentally friendly conditions, due to the influence of structural factors of the starting pyrimidine and a high concentration of alkoxide ions. This method allows the building of pyrimidine-based compound precursors of N-heterocyclic systems.Universidad del Altánticoapplication/pdfenghttp://creativecommons.org/licenses/by-nc/4.0/Attribution-NonCommercial 4.0 Internationalinfo:eu-repo/semantics/openAccesshttp://purl.org/coar/access_right/c_abf2MolbankSNAr Reactions on 2-Amino-4,6-dichloropyrimidine-5-carbaldehydePúblico generalaminationdichloropyrimidinesaromatic substitutioninfo:eu-repo/semantics/articleinfo:eu-repo/semantics/draftArtículohttp://purl.org/coar/version/c_b1a7d7d4d402bccehttp://purl.org/coar/resource_type/c_2df8fbb1BarranquillaIngeniería QuímicaSede NorteFrank, É.; Sz˝oll˝osi, G. Nitrogen-Containing Heterocycles as Significant Molecular Scaffolds for Medicinal and Other Applications. Molecules 2021, 26, 4617. [CrossRef] [PubMed]Kerru, N.; Gummidi, L.; Maddila, S.; Kumar Gangu, K.; Jonnalagadda, S.B. A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications. 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[CrossRef]Zhang, Y.-M.; Gu, M.; Ma, H.; Tang, J.; Lu, W.; Nan, F.-J. An Efficient Synthesis of 2-Chloropyrimidines via Pd-catalyzed Regioselective Dechlorination of 2,4-Dichloropyrimidines in the Presence of NaHCO3. Chin. J. Chem. 2008, 26, 962–964. [CrossRef]Mittersteiner, M.; Farias, F.F.S.; Bonacorso, H.G.; Martins, M.A.P.; Zanatta, N. Ultrasound-assisted synthesis of pyrimidines and their fused derivatives: A review. Ultrason. Sonochem. 2021, 79, 105683. [CrossRef] [PubMed]Marinescu, M. Biginelli Reaction Mediated Synthesis of Antimicrobial Pyrimidine Derivatives and Their Therapeutic Properties. Molecules 2021, 26, 6022. [CrossRef] [PubMed]Thomas, J. Delia. Grignard Reactions Involving Halogenated Pyrimidines. J. Heterocycl. Chem. 2013, 50, 735–745. [CrossRef]Bhaskaran, S.; Padusha, M.S.A.; Sajith, A.M. Application of Palladium Based Precatalytic Systems in the Suzuki-Miyaura Cross-Coupling Reactions of Chloro- Heterocycles. ChemistrySelect 2020, 5, 9005–9016. 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[CrossRef]http://purl.org/coar/resource_type/c_2df8fbb1ORIGINALmolbank-2022-M1426.pdfmolbank-2022-M1426.pdfapplication/pdf1173235https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/767/1/molbank-2022-M1426.pdff411dcec0eb6ee2397d6175f74ceb704MD51CC-LICENSElicense_rdflicense_rdfapplication/rdf+xml; charset=utf-8914https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/767/2/license_rdf24013099e9e6abb1575dc6ce0855efd5MD52LICENSElicense.txtlicense.txttext/plain; charset=utf-81306https://repositorio.uniatlantico.edu.co/bitstream/20.500.12834/767/3/license.txt67e239713705720ef0b79c50b2ececcaMD5320.500.12834/767oai:repositorio.uniatlantico.edu.co:20.500.12834/7672022-11-15 14:11:22.869DSpace de la Universidad de Atlánticosysadmin@mail.uniatlantico.edu.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