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 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.

• 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