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Conversion of 3-amino-4-arylamino-1H-isochromen-1-ones to 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones : synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative
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dc.contributor.author | Vicentes, Daniel E. | |
dc.contributor.author | Romero, Andrea L. | |
dc.contributor.author | Rodríguez, Ricuarte | |
dc.contributor.author | Cobo, Justo | |
dc.contributor.author | Glidewell, Christopher | |
dc.date.accessioned | 2020-04-21T08:30:01Z | |
dc.date.available | 2020-04-21T08:30:01Z | |
dc.date.issued | 2020-05 | |
dc.identifier.citation | Vicentes , D E , Romero , A L , Rodríguez , R , Cobo , J & Glidewell , C 2020 , ' Conversion of 3-amino-4-arylamino-1H-isochromen-1-ones to 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones : synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative ' , Acta Crystallographica Section C Structural Chemistry , vol. 76 , no. 5 , C76 . https://doi.org/10.1107/S2053229620003757 | en |
dc.identifier.issn | 2053-2296 | |
dc.identifier.other | PURE: 267301463 | |
dc.identifier.other | PURE UUID: 08a6e422-22f6-4b07-a77f-5e14b06407e1 | |
dc.identifier.other | Scopus: 85084276589 | |
dc.identifier.uri | https://hdl.handle.net/10023/19831 | |
dc.description | The authors thank 'Centro de Instrumentación Científico-Técnica of Universidad de Jaén' for data collection. The authors thank Universidad de Ciencias Aplicadas y Ambientales (UDCA), Universidad Nacional de Colombia, the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. | en |
dc.description.abstract | An efficient synthesis of 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones, involving the diazotization of 3-amino-4-arylamino-1H-isochromen-1-ones in weakly acidic solution, has been developed and the spectroscopic characterization and crystal structures of four examples are reported. The molecules of 1-phenylisochromeno[3,4-d][1,2,3]triazol-5(1H)-one, C15H9N3O2, (I), are linked into sheets by a combination of C—H⋯N and C—H⋯O hydrogen bonds, while the structures of 1-(2-methylphenyl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, C16H11N3O2, (II), and 1-(3-chlorophenyl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, C15H8ClN3O2, (III), each contain just one hydrogen bond which links the molecules into simple chains, which are further linked into sheets by π-stacking interactions in (II) but not in (III). In the structure of 1-(4-chlorophenyl)isochromeno[3,4-d][1,2,3]triazol-5(1H)-one, (IV), isomeric with (III), a combination of C—H⋯O and C—H⋯π(arene) hydrogen bonds links the molecules into sheets. When compound (II) was exposed to a strong acid in methanol, quantitative conversion occurred to give the ring-opened transesterification product methyl 2-[4-hydroxy-1-(2-methylphenyl)-1H-1,2,3-triazol-5-yl]benzoate, C17H15N3O3, (V), where the molecules are linked by paired O—H⋯O hydrogen bonds to form centrosymmetric dimers. | |
dc.format.extent | 8 | |
dc.language.iso | eng | |
dc.relation.ispartof | Acta Crystallographica Section C Structural Chemistry | en |
dc.rights | Copyright © 2020 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. | en |
dc.subject | Synthesis | en |
dc.subject | Heterocyclic compounds | en |
dc.subject | Isocoumarins | en |
dc.subject | Triazoles | en |
dc.subject | Crystal structure | en |
dc.subject | Molecular conformation | en |
dc.subject | Hydrogen bonding | en |
dc.subject | Supramolecular assembly | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Conversion of 3-amino-4-arylamino-1H-isochromen-1-ones to 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones : synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative | en |
dc.type | Journal article | en |
dc.description.version | Publisher PDF | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | https://doi.org/10.1107/S2053229620003757 | |
dc.description.status | Peer reviewed | en |
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