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An eco-friendly protocol for synthesis of thiourea derivatives: 1-benzoyl-3-benzylguanidine and 1-benzoyl-3-benzyl-O-ethylisourea. A possible non-purely thermal microwave assisted reaction

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dc.contributor.authorMarquez, H.
dc.contributor.authorLoupy, A.
dc.contributor.authorCalderon, O.
dc.contributor.authorPerez, E. R.
dc.contributor.institutionUniversidade Estadual Paulista (Unesp)
dc.contributor.institutionUniv La Habana
dc.contributor.institutionUniv Paris 11
dc.contributor.institutionUniversidade Federal do Rio de Janeiro (UFRJ)
dc.date.accessioned2014-05-20T15:30:13Z
dc.date.available2014-05-20T15:30:13Z
dc.date.issued2006-03-13
dc.description.abstract1-Benzoyl-3-benzylguanidine and 1-benzoyl-3-benzyl-O-ethylisourea were synthesized in good yields (68 and 76%, respectively) from 1-benzoyl-3-benzylthiourea and benzoyl-ethylthiocarbamate in dry media conditions using KF-Al2O3 under microwave irradiation. Strong nucleophilic amines promoted the sulfur elimination by attack on the thiocarbonyl group in both thiourea and thiocarbamates to afford guanidines and isourea, respectively. Transesterification products were obtained from p-TsOH catalyzed reaction of thiocarbamate with alcohols under MW-solvent-free conditions. Very important non-purely thermal MW specific effects were evidenced and attributed to stabilization by coulombic interactions between materials and waves. (c) 2005 Elsevier Ltd. All rights reserved.en
dc.description.affiliationUNESP, Fac Ciências & Tecnol, BR-19060080 Presidente Prudente, SP, Brazil
dc.description.affiliationUniv La Habana, Fac Quim, Lab Sintesis Organ, Havana 10400, Cuba
dc.description.affiliationUniv Paris 11, Lab React Select Supports, ICMMO, UMR 8615, F-91405 Orsay, France
dc.description.affiliationUFRJ, Inst Quim, Lab 641, Rio de Janeiro, Brazil
dc.description.affiliationUnespUNESP, Fac Ciências & Tecnol, BR-19060080 Presidente Prudente, SP, Brazil
dc.format.extent2616-2621
dc.identifierhttp://dx.doi.org/10.1016/j.tet.2005.12.037
dc.identifier.citationTetrahedron. Oxford: Pergamon-Elsevier B.V., v. 62, n. 11, p. 2616-2621, 2006.
dc.identifier.doi10.1016/j.tet.2005.12.037
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/11449/39647
dc.identifier.wosWOS:000235763900022
dc.language.isoeng
dc.publisherElsevier B.V.
dc.relation.ispartofTetrahedron
dc.relation.ispartofjcr2.377
dc.relation.ispartofsjr0,800
dc.rights.accessRightsAcesso restritopt
dc.sourceWeb of Science
dc.subject1-benzoyl-3-benzylguanidinept
dc.subject1-benzoyl-3-benzyl-O-ethylisoureapt
dc.subjectthiocarbamatespt
dc.subjectmicrowave irradiationpt
dc.subjectsolvent-free conditionspt
dc.titleAn eco-friendly protocol for synthesis of thiourea derivatives: 1-benzoyl-3-benzylguanidine and 1-benzoyl-3-benzyl-O-ethylisourea. A possible non-purely thermal microwave assisted reactionen
dc.typeArtigopt
dcterms.licensehttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dcterms.rightsHolderElsevier B.V.
dspace.entity.typePublication
unesp.campusUniversidade Estadual Paulista (UNESP), Faculdade de Ciências e Tecnologia, Presidente Prudentept

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