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dc.contributor.authorVicentes, Daniel E.spa
dc.contributor.authorRodríguez, Ricaurtespa
dc.contributor.authorOchoa, Patriciaspa
dc.contributor.authorCobo, Justospa
dc.contributor.authorGlidewell, Glidewelldspa
dc.date.accessioned2019-11-08T18:52:01Zspa
dc.date.available2019-11-08T18:52:01Zspa
dc.date.issued2019spa
dc.identifier.citationVicentes, D. E., Rodríguez, R., Ochoa, P., Cobo, J., & Glidewell, C. (2019). A concise and efficient synthesis of amino-substituted (1H-benzo[d]imidazol-1-yl)pyrimidine hybrids: Synthetic sequence and the molecular and supramolecular structures of six examples. Acta Crystallographica Section C: Structural Chemistry, 75, 1405-1416. doi:10.1107/S2053229619012087spa
dc.identifier.urihttps://www.scopus.com/search/form.uri?display=basicspa
dc.description.abstractA concise and efficient synthesis of a series of amino-substituted benzimidazole-pyrimidine hybrids has been developed, starting from the readily available N 4-(2-aminophenyl)-6-methoxy-5-nitrosopyrimidine-2,4-diamine. In each of N 5-benzyl-6-methoxy-4-(2-phenyl-1H-benzo[d]imidazol-1-yl)pyrimidine-2,5-diamine, C25H22N6O, (I), 6-methoxy-N 5-(4-methoxybenzyl)-4-[2-(4-methoxyphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, C27H26N6O3, (III), 6-methoxy-N 5-(4-nitrobenzyl)-4-[2-(4-nitrophenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, C25H20N8O5, (IV), the molecules are linked into three-dimensional framework structures, using different combinations of N-H⋯N, N-H⋯O, C-H⋯O, C-H⋯N and C-H⋯π hydrogen bonds in each case. Oxidative cleavage of 6-methoxy-N 5-(4-methylbenzyl)-4-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, (II), with diiodine gave 6-methoxy-4-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidine-2,5-diamine, which crystallized as a monohydrate, C19H18N6O·H2O, (V), and reaction of (V) with trifluoroacetic acid gave two isomeric products, namely N-{5-amino-6-methoxy-6-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidin-2-yl}-2,2,2-trifluoroacetamide, which crystallized as an ethyl acetate monosolvate, C21H17F3N6O2·C4H8O2, (VI), and N-{2-amino-6-methoxy-4-[2-(4-methylphenyl)-1H-benzo[d]imidazol-1-yl]pyrimidin-5-yl}-2,2,2-trifluoroacetamide, which crystallized as a methanol monosolvate, C21H17F3N6O2·CH4O, (VIIa). For each of (V), (VI) and (VIIa), the supramolecular assembly is two-dimensional, based on different combinations of O-H⋯N, N-H⋯O, N-H⋯N, C-H⋯O and C-H⋯π hydrogen bonds in each case. Comparisons are made with some related structures.eng
dc.format.mimetypeapplication/pdfspa
dc.language.isoengspa
dc.relation.ispartofseriesActa Crystallographica Section C: Structural Chemistry;Vol.75, No.1, Oct 2019 páginas 1405-1416spa
dc.rightsDerechos Reservados - Universidad de Ciencias Aplicadas y Ambientalesspa
dc.rights.urihttps://creativecommons.org/licenses/by-nc-sa/4.0/spa
dc.sourcehttps://www.scopus.com/search/form.uri?display=basicspa
dc.sourcehttps://www.scopus.com/search/form.uri?display=basicspa
dc.subject.meshEnlaces de Hidrógenospa
dc.subject.meshCarbón Orgánicospa
dc.subject.meshBencimidazolesspa
dc.subject.meshConformación Molecularspa
dc.titleA concise and efficient synthesis of amino-substituted (1H-benzo[d]imidazol-1-yl)pyrimidine hybrids: Synthetic sequence and the molecular and supramolecular structures of six examplesspa
dc.typeArtículo de revistaspa
dc.rights.accessrightsinfo:eu-repo/semantics/openAccessspa
dc.identifier.doi10.1107/S2053229619012087spa
dc.rights.creativecommonsAtribución-NoComercial-CompartirIgual 4.0 Internacional (CC BY-NC-SA 4.0)spa
dc.subject.proposalBenzimidazolespa
dc.subject.proposalCrystal structurespa
dc.subject.proposalDisorderspa
dc.subject.proposalHydrogen bondingspa
dc.subject.proposalMolecular conformationspa
dc.subject.proposalNMR spectraspa
dc.subject.proposalPyrimidinespa
dc.subject.proposalSupramolecular assemblyspa
dc.subject.proposalSynthesisspa
dc.type.coarhttp://purl.org/coar/resource_type/c_6501spa
dc.type.driverinfo:eu-repo/semantics/articlespa
dc.type.versioninfo:eu-repo/semantics/publishedVersionspa
dc.type.contentTextspa
dc.type.redcolhttp://purl.org/redcol/resource_type/ARTspa
oaire.accessrightshttp://purl.org/coar/access_right/c_abf2spa
oaire.versionhttp://purl.org/coar/version/c_970fb48d4fbd8a85spa


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