A calix[n]arene-catalysed three-component povarov reaction: microwave-assisted synthesis of julolidines and mechanistic insights

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dc.creatorPaula Aline da Silva Abranches
dc.creatorWalysson Ferreira de Paiva
dc.creatorÂngelo de Fátima
dc.creatorFelipe Terra Martins
dc.creatorSergio Antonio Fernandes
dc.date.accessioned2024-09-13T18:31:08Z
dc.date.accessioned2025-09-08T22:52:22Z
dc.date.available2024-09-13T18:31:08Z
dc.date.issued2018
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipOutra Agência
dc.identifier.doihttps://doi.org/10.1021/acs.joc.7b02532
dc.identifier.issn0022-3263
dc.identifier.urihttps://hdl.handle.net/1843/76459
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofThe Journal of Organic Chemistry
dc.rightsAcesso Restrito
dc.subjectCalixarenos
dc.subjectCompostos heterocíclicos
dc.subjectAldeídos
dc.subjectCatalisadores
dc.subjectReações químicas
dc.subjectIons
dc.subjectReações de substituição
dc.subject.otherPovarov reaction
dc.subject.otherCalixarenes
dc.subject.otherOrganocatalyst
dc.subject.otherJulolidine
dc.titleA calix[n]arene-catalysed three-component povarov reaction: microwave-assisted synthesis of julolidines and mechanistic insights
dc.typeArtigo de periódico
local.citation.epage1771
local.citation.issue4
local.citation.spage1761
local.citation.volume83
local.description.resumoA new one-pot cascade reaction-based application of Povarov reactions with a p-sulfonic acid calix[4]arene catalyst for the synthesis of a series of 34 julolidine derivatives with substituents at C8 or C9 in good to excellent yields is reported. These microwave-assisted reactions proceeded efficiently, had short reaction times, were metal-free, were low cost, and used an inexpensive, easily available and nontoxic catalyst. These advantages, along with a simple workup procedure, make this protocol a very efficient and green alternative to the traditional methods for constructing these types of N-heterocyclic skeletons. In addition, this protocol allows the formation of julolidine structures, which requires the construction of four new C–C bonds and two C–N bonds. A mechanism for the Povarov reaction involving a stepwise sequence via ionic intermediates was proposed and validated.
local.identifier.orcidhttps://orcid.org/0000-0002-8663-157X
local.identifier.orcidhttps://orcid.org/0000-0003-3476-5477
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0001-9004-0927
local.identifier.orcidhttps://orcid.org/0000-0003-3054-3316
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://pubs.acs.org/doi/10.1021/acs.joc.7b02532?src=getftr#

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