New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones,Synthesis

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New Synthesis of Pyrazolo[3,4-b]pyridine Derivatives Based on 5-Aminopyrazole and Azlactones
Synthesis ( IF 2.2 ) Pub Date : 2024-01-08 , DOI: 10.1055/a-2218-9177
Vladislav Shuvalov _{1,

2} , Anton L. Shatsauskas _{3,

4} , Tatyana Yu. Zheleznova ₅ , Anastasia S. Kostyuchenko _{3,

4} , Alexander S. Fisyuk _{4,

6}

Affiliation

Reaction of 5-amino-3-methyl-1-phenyl-1H-pyrazole with azlactones under solvent-free conditions with heating furnished tetrahydro-1H-pyrazolo[3,4-b]pyridines. The latter were converted to oxazolo[5,4-b]pyrazolo[4,3-e]pyridines by the action with POCl₃ on air. Further reaction of oxazolo[5,4-b]pyrazolo[4,3-e]pyridines with hydrazine hydrate and alkali led to the formation of 5-amino-1,7-dihydro-6H-pyrazolo[3,4-b]pyridin-6-ones, which reacted with aluminum chloride to yield 3,4-dihydro-5H-pyrazolo[4,3-f][1,7]naphthyridin-5-ones. Some of the synthesized compounds show antioxidant activity or are effective phosphors.

中文翻译：

基于5-氨基吡唑和吖内酯的吡唑并[3,4-b]吡啶衍生物的新合成

5-氨基-3-甲基-1-苯基-1H-吡唑与吖内酯在无溶剂条件下加热反应，得到四氢-1H-吡唑并[3,4- b ]吡啶。后者在空气中与POCl ₃作用转化为恶唑并[5,4- b ]吡唑并[4,3- e ]吡啶。恶唑并[5,4- b ]吡唑并[4,3- e ]吡啶与水合肼和碱进一步反应生成5-氨基-1,7-二氢-6H-吡唑并[3,4- b ]吡啶-6-酮，与氯化铝反应生成3,4-二氢-5H-吡唑并[4,3- f ][1,7]萘啶-5-酮。一些合成的化合物表现出抗氧化活性或者是有效的磷光体。

更新日期：2024-01-09

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