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

Vladislav Yu Shuvalov; Ekaterina Yu Vlasova; Tatyana Yu Zheleznova; Alexander S Fisyuk

doi:10.3762/bjoc.19.83

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

Beilstein J Org Chem. 2023 Aug 2:19:1155-1160. doi: 10.3762/bjoc.19.83. eCollection 2023.

Authors

Vladislav Yu Shuvalov¹, Ekaterina Yu Vlasova², Tatyana Yu Zheleznova¹, Alexander S Fisyuk^{1

2}

Affiliations

¹ Laboratory of New Organic Materials, Omsk State Technical University, 11 Mira Ave., 644050 Omsk, Russian Federation.
² Department of Organic and Analytical Chemistry, F. M. Dostoevsky Omsk State University, Mira Ave., 55a, 644077 Omsk, Russian Federation.

Abstract

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.

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

Grants and funding

This work was supported by the Russian Science Foundation (grant No. 22-13-00356).