基于5-氨基吡唑和乙内酰脲的4-芳基吡唑并[3,4-]吡啶-6-酮的新型一锅法合成
New one-pot synthesis of 4-arylpyrazolo[3,4-]pyridin-6-ones based on 5-aminopyrazoles and azlactones.
作者信息
Shuvalov Vladislav Yu, Vlasova Ekaterina Yu, Zheleznova Tatyana Yu, Fisyuk Alexander S
机构信息
Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave., 644050 Omsk, Russian Federation.
Department of Organic and Analytical Chemistry, F. M. Dostoevsky Omsk State University, Mira Ave., 55a, 644077 Omsk, Russian Federation.
出版信息
Beilstein J Org Chem. 2023 Aug 2;19:1155-1160. doi: 10.3762/bjoc.19.83. eCollection 2023.
An effective one-pot strategy was developed for the synthesis of 4-arylpyrazolo[3,4-]pyridin-6-ones from pyrazolo[3,4-]pyridin-6-ones, obtained by reacting 5-aminopyrazoles with 4-arylidene-2-phenyloxazol-5(4)-ones (azlactones) under solvent-free conditions, through subsequent elimination of a benzamide molecule in a superbasic medium (-BuOK/DMSO). The fluorescent properties of the synthesized compounds were studied. 4-Arylpyrazolo[3,4-]pyridin-6-ones luminesce in the region of 409-440 nm with a quantum yield of 0.09-0.23 when irradiated with UV light.
开发了一种有效的一锅法策略，用于从吡唑并[3,4 -]吡啶 - 6 - 酮合成4 - 芳基吡唑并[3,4 -]吡啶 - 6 - 酮。吡唑并[3,4 -]吡啶 - 6 - 酮是通过在无溶剂条件下使5 - 氨基吡唑与4 - 亚芳基 - 2 - 苯基恶唑 - 5(4) - 酮（恶唑烷酮）反应得到的，随后在超强碱性介质（叔丁醇钾/二甲基亚砜）中消除一个苯甲酰胺分子。研究了合成化合物的荧光性质。当用紫外光照射时，4 - 芳基吡唑并[3,4 -]吡啶 - 6 - 酮在409 - 440 nm区域发光，量子产率为0.09 - 0.23。
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