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

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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.
Acta Crystallographica Section C ( IF 0.7 ) Pub Date : 2020-04-20 , DOI: 10.1107/s2053229620003757
Daniel E Vicentes ₁ , Andrea L Romero ₁ , Ricuarte Rodríguez ₂ , Justo Cobo ₃ , Christopher Glidewell ₄

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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.

中文翻译：

3-氨基-4-芳基氨基-1H-异色烯-1-酮转化为 1-芳基异色烯[3,4-d][1,2,3]三唑-5(1H)-酮：合成、光谱表征和四种产品和一种开环衍生物的结构。

1-芳基异色烯[3,4-d][1,2,3]三唑-5(1H)-酮的有效合成，涉及 3-氨基-4-芳氨基-1H-异色烯-1-酮的重氮化弱酸性溶液已经开发出来，并报告了四个例子的光谱表征和晶体结构。 1-苯基异色烯[3,4-d][1,2,3]三唑-5(1H)-酮 C15H9N3O2, (I) 分子通过 CH...N 和 CH 的组合连接成片状...O 氢键，而 1-(2-甲基苯基)异色烯基[3,4-d][1,2,3]三唑-5(1H)-one、C16H11N3O2、(II) 和 1 的结构-(3-氯苯基)异色烯基[3,4-d][1,2,3]三唑-5(1H)-one，C15H8ClN3O2，(III)，每个仅含有一个氢键，将分子连接成简单的链，它们通过 (II) 中的 π 堆积相互作用进一步连接成片，但在 (III) 中则不然。 1-(4-氯苯基)异色烯基[3,4-d][1,2,3]三唑-5(1H)-酮的结构中，(IV)与(III)是同分异构体，是CH的组合。 ..O 和 CH...π(芳烃) 氢键将分子连接成片状。当化合物(II)在甲醇中暴露于强酸时，发生定量转化，得到开环酯交换产物甲基2-[4-羟基-1-(2-甲基苯基)-1H-1,2,3-三唑-5-基]苯甲酸酯，C17H15N3O3，(V)，其中分子通过成对的 OH...O 氢键连接形成中心对称二聚体。

更新日期：2020-04-20

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