2,5-diketopiperazines via intramolecular N-alkylation of Ugi adducts: a contribution to the synthesis, density functional theory study, X-ray characterization, and potential herbicide application

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dc.creatorMendes, Lorena Lessa
dc.creatorVarejão, Jodieh Oliveira Santana
dc.creatorSousa, José Antonio de
dc.creatorCarneiro, José Walkimar de Mesquita
dc.creatorValdo, Ana Karoline Silva Mendanha
dc.creatorMartins, Felipe Terra
dc.creatorFerreira, Bruno Wesley
dc.creatorBarreto, Robert Weingart
dc.creatorSilva, Toshik Iarley da
dc.creatorKohlhoff, Markus
dc.creatorPilau, Eduardo Jorge
dc.creatorVarejão, Eduardo Vinícius Vieira
dc.date.accessioned2023-11-09T13:01:05Z
dc.date.available2023-11-09T13:01:05Z
dc.date.issued2022
dc.description.abstractTo investigate the herbicidal potential of 2,5-diketopiperazines (2,5-DKPs), we applied a known protocol to produce a series of 2,5-DKPs through intramolecular N-alkylation of Ugi adducts. However, the method was not successful for the cyclization of adducts presenting aromatic rings with some substituents at the ortho position. Results from DFT calculations showed that the presence of voluminous groups at the ortho position of a benzene ring results in destabilization of the transition structure. Lower activation enthalpies for the SN2-type cyclization of Ugi adducts were obtained when bromine, instead of a chlorine anion, is the leaving group, indicating that the activation enthalpy for the cyclization step controls the formation of the 2,5-DKP. Some Ugi adducts and 2,5-DKPs formed crystals with suitable qualities for single-crystal X-ray diffraction data collection. Phytotoxic damage of some 2,5-DKPs on leaves of the weed Euphorbia heterophylla did not differ from those caused by the commercial herbicide diquat.
dc.identifier.citationMENDES, Lorena L. et al. 2,5-diketopiperazines via intramolecular N-alkylation of Ugi adducts: a contribution to the synthesis, density functional theory study, X-ray characterization, and potential herbicide application. Journal of Agricultural and Food Chemistry, Washington, v. 70, n. 6, p. 1799-1809, 2022. DOI: 10.1021/acs.jafc.1c07790. Disponível em: https://pubs.acs.org/doi/10.1021/acs.jafc.1c07790. Acesso em: 7 nov. 2023.
dc.identifier.doi10.1021/acs.jafc.1c07790
dc.identifier.issne- 1520-5118
dc.identifier.issn0021-8561
dc.identifier.urihttps://pubs.acs.org/doi/10.1021/acs.jafc.1c07790
dc.language.isoeng
dc.publisher.countryEstados unidos
dc.publisher.departmentInstituto de Química - IQ (RMG)
dc.relation.ispartofserieshttps://pubs.acs.org/doi/10.1021/acs.jafc.1c07790
dc.relation.ispartofseries10.1021/acs.jafc.1c07790
dc.relation.ispartofseries0021-8561
dc.relation.ispartofseriese- 1520-5118
dc.rightsAcesso Restrito
dc.subjectUgi 4-CR
dc.subjectMulticomponent reaction
dc.subjectIsocyanides
dc.subjectWild poinsettia
dc.subjectHerbicides
dc.title2,5-diketopiperazines via intramolecular N-alkylation of Ugi adducts: a contribution to the synthesis, density functional theory study, X-ray characterization, and potential herbicide application
dc.typeArtigo

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