Factorial study to assess an ultrasonic methodology for the allylation of 4-chloroaniline

dc.citation.issue2
dc.citation.volume6
dc.contributor.authorSantos Nascimento, Lillian Ferreira [UNIFESP]
dc.contributor.authorSantos Fernandes, Joao Paulo [UNIFESP]
dc.coverageBerlin
dc.date.accessioned2020-07-17T14:02:23Z
dc.date.available2020-07-17T14:02:23Z
dc.date.issued2017
dc.description.abstractN-allylanilines are important compounds that are used to access several bioactive compounds containing indole and dihydroindole nucleus. However, their preparation through allylation can lead to the undesirable N, N-diallyl byproduct. In this work, the N-allylation of 4-chloroaniline was studied. In order to accelerate the process and maximize the monoallylated: diallylated ratio, we reported two full factorial studies to transpose the conventional synthetic procedure to an ultrasound (US) methodology. The evaluated factors were temperature, quantity of reagents (allyl bromide and K2CO3), reaction time, and methodology (conventional or US). The results showed that US did not change the monoallylated: diallylated ratio, but significantly improved the reaction rate, giving increased average monoallylated and total yields of 11.4% and 18.1%, respectively (p < 0.05). The proposed US methodology gave the same yields and product ratio in a 4-h reaction time than the conventional 24-h procedure, without heating and using only an inexpensive US bath to conduct the reactions.en
dc.description.affiliationUniv Fed Sao Paulo, Dept Ciencias Exatas & Terra, Rua Sao Nicolau 210,2 Andar, BR-09913030 Diadema, SP, Brazil
dc.description.affiliationUnifespUniv Fed Sao Paulo, Dept Ciencias Exatas & Terra, Rua Sao Nicolau 210,2 Andar, BR-09913030 Diadema, SP, Brazil
dc.description.provenanceMade available in DSpace on 2020-07-17T14:02:23Z (GMT). No. of bitstreams: 0 Previous issue date: 2017en
dc.description.sourceWeb of Science
dc.description.sponsorshipSao Paulo state agency FAPESP
dc.description.sponsorshipBrazilian agency CNPq
dc.description.sponsorshipIDFAPESP: 2013/20479-9
dc.description.sponsorshipIDCNPq: 455411/2014-0
dc.format.extent203-209
dc.identifierhttp://dx.doi.org/10.1515/gps-2016-0122
dc.identifier.citationGreen Processing And Synthesis. Berlin, v. 6, n. 2, p. 203-209, 2017.
dc.identifier.doi10.1515/gps-2016-0122
dc.identifier.issn2191-9542
dc.identifier.urihttps://repositorio.unifesp.br/handle/11600/54783
dc.identifier.wosWOS:000403508700008
dc.language.isoeng
dc.publisherWalter De Gruyter Gmbh
dc.relation.ispartofGreen Processing And Synthesis
dc.rightsAcesso aberto
dc.subjectfactorial designen
dc.subjectN-allyl-4-chloroanilineen
dc.subjectN-allylationen
dc.subjectultrasonic bathen
dc.subjectultrasound-assisted synthesisen
dc.titleFactorial study to assess an ultrasonic methodology for the allylation of 4-chloroanilineen
dc.typeArtigo
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