https://repository.udca.edu.co/handle/11158/3694
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 |
Authors: | Vicentes, Daniel E. Romero, Andrea L. Rodríguez, Ricaurte Cobo, Justo Glidewell, Christopher |
Issue Date: | 2020 |
Citation: | Vicentes, D. E., Romero, A. L., Rodriguez, 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, 76, 446-453. doi:10.1107/S2053229620003757 |
Series/Report no.: | Acta Crystallographica Section C: Structural Chemistry;Vol. 76, May 1 2020, páginas 446-453 |
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. |
URI: | https://journals.iucr.org/c/issues/2020/05/00/sk3747/index.html |
Appears in Collections: | CCB. Artículos indexados en Scopus |
File | Description | Size | Format | |
---|---|---|---|---|
Conversion of 3-amino-4-arylamino.pdf | 1,58 MB | Adobe PDF | ![]() View/Open |
This item is licensed under a Creative Commons License