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
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 molecule...
- Autores:
-
Vicentes, Daniel E.
Romero, Andrea L.
Rodríguez, Ricaurte
Cobo, Justo
Glidewell, Christopher
- Tipo de recurso:
- Article of journal
- Fecha de publicación:
- 2020
- Institución:
- Universidad de Ciencias Aplicadas y Ambientales U.D.C.A
- Repositorio:
- Repositorio Institucional UDCA
- Idioma:
- eng
- OAI Identifier:
- oai:repository.udca.edu.co:11158/3694
- Acceso en línea:
- https://journals.iucr.org/c/issues/2020/05/00/sk3747/index.html
- Palabra clave:
- Isocumarinas
Enlace de Hidrógeno
Compuestos Heterocíclicos
Triazoles
Síntesis química
Crystal structure
Heterocyclic compounds
Hydrogen bonding
Isocoumarins
Molecular conformation
Supramolecular assembly
Synthesis
Triazoles
- Rights
- openAccess
- License
- Derechos Reservados - Universidad de Ciencias Aplicadas y Ambientales
| Summary: | 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. |
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