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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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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. / Vicentes, Daniel E.; Romero, Andrea L.; Rodríguez, Ricuarte; Cobo, Justo; Glidewell, Christopher.

In: Acta Crystallographica Section C Structural Chemistry, Vol. 76, No. 5, C76, 05.2020.

Research output: Contribution to journalArticlepeer-review

Harvard

Vicentes, DE, Romero, AL, 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

APA

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, 76(5), [C76]. https://doi.org/10.1107/S2053229620003757

Vancouver

Vicentes DE, Romero AL, Rodríguez R, Cobo J, Glidewell C. 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. 2020 May;76(5). C76. https://doi.org/10.1107/S2053229620003757

Author

Vicentes, Daniel E. ; Romero, Andrea L. ; Rodríguez, Ricuarte ; Cobo, Justo ; Glidewell, Christopher. / 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. In: Acta Crystallographica Section C Structural Chemistry. 2020 ; Vol. 76, No. 5.

Bibtex - Download

@article{08a6e42222f64b07a77f5e14b06407e1,
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",
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.",
keywords = "Synthesis, Heterocyclic compounds, Isocoumarins, Triazoles, Crystal structure, Molecular conformation, Hydrogen bonding, Supramolecular assembly",
author = "Vicentes, {Daniel E.} and Romero, {Andrea L.} and Ricuarte Rodr{\'i}guez and Justo Cobo and Christopher Glidewell",
note = "The authors thank 'Centro de Instrumentaci{\'o}n Cient{\'i}fico-T{\'e}cnica of Universidad de Ja{\'e}n' for data collection. The authors thank Universidad de Ciencias Aplicadas y Ambientales (UDCA), Universidad Nacional de Colombia, the Consejer{\'i}a de Innovaci{\'o}n, Ciencia y Empresa (Junta de Andaluc{\'i}a, Spain) and the Universidad de Ja{\'e}n for financial support.",
year = "2020",
month = may,
doi = "10.1107/S2053229620003757",
language = "English",
volume = "76",
journal = "Acta Crystallographica Section C Structural Chemistry",
issn = "2053-2296",
publisher = "International Union of Crystallography",
number = "5",

}

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TY - JOUR

T1 - Conversion of 3-amino-4-arylamino-1H-isochromen-1-ones to 1-arylisochromeno[3,4-d][1,2,3]triazol-5(1H)-ones

T2 - synthesis, spectroscopic characterization and the structures of four products and one ring-opened derivative

AU - Vicentes, Daniel E.

AU - Romero, Andrea L.

AU - Rodríguez, Ricuarte

AU - Cobo, Justo

AU - Glidewell, Christopher

N1 - 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.

PY - 2020/5

Y1 - 2020/5

N2 - 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.

AB - 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.

KW - Synthesis

KW - Heterocyclic compounds

KW - Isocoumarins

KW - Triazoles

KW - Crystal structure

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

U2 - 10.1107/S2053229620003757

DO - 10.1107/S2053229620003757

M3 - Article

VL - 76

JO - Acta Crystallographica Section C Structural Chemistry

JF - Acta Crystallographica Section C Structural Chemistry

SN - 2053-2296

IS - 5

M1 - C76

ER -

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