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

An effective one-pot strategy was developed for the synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones from pyrazolo[3,4-b]pyridin-6-ones, obtained by reacting 5-aminopyrazoles with 4-arylidene-2-phenyloxazol-5(4H)-ones (azlactones) under solvent-free conditions, through subsequent elimination of a be...

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Autores principales: Shuvalov, Vladislav Yu, Vlasova, Ekaterina Yu, Zheleznova, Tatyana Yu, Fisyuk, Alexander S
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2023
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407779/
https://www.ncbi.nlm.nih.gov/pubmed/37560137
http://dx.doi.org/10.3762/bjoc.19.83
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author Shuvalov, Vladislav Yu
Vlasova, Ekaterina Yu
Zheleznova, Tatyana Yu
Fisyuk, Alexander S
author_facet Shuvalov, Vladislav Yu
Vlasova, Ekaterina Yu
Zheleznova, Tatyana Yu
Fisyuk, Alexander S
author_sort Shuvalov, Vladislav Yu
collection PubMed
description An effective one-pot strategy was developed for the synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones from pyrazolo[3,4-b]pyridin-6-ones, obtained by reacting 5-aminopyrazoles with 4-arylidene-2-phenyloxazol-5(4H)-ones (azlactones) under solvent-free conditions, through subsequent elimination of a benzamide molecule in a superbasic medium (t-BuOK/DMSO). The fluorescent properties of the synthesized compounds were studied. 4-Arylpyrazolo[3,4-b]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.
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spelling pubmed-104077792023-08-09 New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones Shuvalov, Vladislav Yu Vlasova, Ekaterina Yu Zheleznova, Tatyana Yu Fisyuk, Alexander S Beilstein J Org Chem Full Research Paper An effective one-pot strategy was developed for the synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones from pyrazolo[3,4-b]pyridin-6-ones, obtained by reacting 5-aminopyrazoles with 4-arylidene-2-phenyloxazol-5(4H)-ones (azlactones) under solvent-free conditions, through subsequent elimination of a benzamide molecule in a superbasic medium (t-BuOK/DMSO). The fluorescent properties of the synthesized compounds were studied. 4-Arylpyrazolo[3,4-b]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. Beilstein-Institut 2023-08-02 /pmc/articles/PMC10407779/ /pubmed/37560137 http://dx.doi.org/10.3762/bjoc.19.83 Text en Copyright © 2023, Shuvalov et al. https://creativecommons.org/licenses/by/4.0/This is an open access article licensed under the terms of the Beilstein-Institut Open Access License Agreement (https://www.beilstein-journals.org/bjoc/terms/terms), which is identical to the Creative Commons Attribution 4.0 International License (https://creativecommons.org/licenses/by/4.0 (https://creativecommons.org/licenses/by/4.0/) ). The reuse of material under this license requires that the author(s), source and license are credited. Third-party material in this article could be subject to other licenses (typically indicated in the credit line), and in this case, users are required to obtain permission from the license holder to reuse the material.
spellingShingle Full Research Paper
Shuvalov, Vladislav Yu
Vlasova, Ekaterina Yu
Zheleznova, Tatyana Yu
Fisyuk, Alexander S
New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
title New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
title_full New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
title_fullStr New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
title_full_unstemmed New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
title_short New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
title_sort new one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10407779/
https://www.ncbi.nlm.nih.gov/pubmed/37560137
http://dx.doi.org/10.3762/bjoc.19.83
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