New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones

Submitting author affiliation:
F. M. Dostoevskii Omsk State University,Omsk State Technical University, Omsk, Russian Federation

Beilstein Arch. 2023, 202323.

Published 31 May 2023

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An efficient one-pot strategy for the synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on readily available compounds was developed. The interaction of 5-aminopyrazole with 4-arylidene-2-phenyloxazol-5(4H)-ones (azlactones) under solvent-free conditions gave 1,4,5,7-tetrahydro-6H-pyrazolo[3,4-b]pyridine-6-ones with a benzamide group at the C(5) position. Subsequent elimination of the benzamide molecule in a superbasic medium (t-BuOK/DMSO) leads to 4-arylpyrazolo[3,4-b]pyridin-6-ones in good yield. The luminescent properties of the obtained compounds were also studied.

Keywords: 5-aminopyrazole; azlactone; elimination; fluorescence; one-pot synthesis; pyrazolo[3,4-b]pyridin-6-one

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Shuvalov, V. Y.; Vlasova, E. Y.; Zheleznova, T. Y.; Fisyuk, A. S. Beilstein Arch. 2023, 202323. doi:10.3762/bxiv.2023.23.v1

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