Calix[n]arene-catalysed three-component Povarov reaction: microwave-assisted synthesis of julolidines and mechanistic insights

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dc.creatorAbranches, Paula Aline da Silva
dc.creatorPaiva, Walysson Ferreira de
dc.creatorFátima, Ângelo de
dc.creatorMartins, Felipe Terra
dc.creatorFernandes, Sergio Antonio
dc.date.accessioned2023-11-29T11:35:32Z
dc.date.available2023-11-29T11:35:32Z
dc.date.issued2018
dc.description.abstractA 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.
dc.identifier.citationABRANCHES, Paula Aline da Silva et al. Calix[n]arene-catalysed three-component Povarov reaction: microwave-assisted synthesis of julolidines and mechanistic insight. The Journal of Organic Chemistry, Washington, v. 83, n. 4, p. 1761-1771, 2018. DOI: 10.1021/acs.joc.7b02532. Disponível em: https://pubs.acs.org/doi/10.1021/acs.joc.7b02532. Acesso em: 28 nov. 2023.
dc.identifier.doi10.1021/acs.joc.7b02532
dc.identifier.issn0022-3263
dc.identifier.issne- 1520-6904
dc.identifier.urihttps://pubs.acs.org/doi/10.1021/acs.joc.7b02532
dc.language.isoeng
dc.publisher.countryEstados unidos
dc.publisher.departmentInstituto de Química - IQ (RMG)
dc.rightsAcesso Restrito
dc.titleCalix[n]arene-catalysed three-component Povarov reaction: microwave-assisted synthesis of julolidines and mechanistic insights
dc.typeArtigo

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