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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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Date
05/2020
Author
Vicentes, Daniel E.
Romero, Andrea L.
Rodríguez, Ricuarte
Cobo, Justo
Glidewell, Christopher
Keywords
Synthesis
Heterocyclic compounds
Isocoumarins
Triazoles
Crystal structure
Molecular conformation
Hydrogen bonding
Supramolecular assembly
QD Chemistry
DAS
Metadata
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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.
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
Publication
Acta Crystallographica Section C Structural Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2053229620003757
ISSN
2053-2296
Type
Journal article
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.
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.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/19831

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