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

Abstract

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.

Key words

azlactone - 5-aminopyrazole - antioxidant - fluorescence - rearrangement - naphthyridine - pyrazolo[3,4-b]pyridine - pyridone–pyridol tautomerism

Publication History

Received: 22 October 2023

Accepted after revision: 28 November 2023

Accepted Manuscript online:
28 November 2023

Article published online:
08 January 2024

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