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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

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

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

Acta Crystallogr C Struct Chem. 2020 May 1;76(Pt 5):446-453.

PMID: 32367825

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
LS7931243	1-(3-Chlorophenyl)-1H-pyrazol-4-ylboronic acid			Price

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