Crystal structure determination of N- and O-alkylated tautomers of 1-(2-pyridinyl)-5-hydroxypyrazole

Sadu, Venkata S.; Choi, Yoon Mi; Kamma, Koteswara R.; Kim, Chong Hyeak; Lee, Kee In

doi:10.1016/j.molstruc.2020.128272

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“…Indeed, a large number of arylated pyrazoles have been synthesized and proven to be effective inhibitors of COX-2, p38 MAP kinase, and CDK2/Cyclin A [1]. In particular, we were involved in the tautomeric transformations of 5-pyrazolone derivatives for the synthesis of NADPH oxidase inhibitors [2][3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Structural Requirements of 1-(2-Pyridinyl)-5-pyrazolones for Disproportionation of Boronic Acids

Cho

Sadu²,

Han

et al. 2021

Molecules

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We observed an unusual formation of four-coordinate boron(III) complexes from the reaction of 1-(2-pyridinyl)-5-pyrazolone derivatives with arylboronic acids in the basic media. The exact mechanism is not clear; however, the use of unprotected boronic acid and the presence of a bidentate ligand appeared to be the key structural requirements for the transformation. The results suggest that base-promoted disproportionation of arylboronic acid with the assistance of the [N,O]-bidentate ligation of 1-(2-pyridinyl)-5-pyrazolone should take place and facilitate the formation of pyrazole diarylborinate. Experiments to obtain a deeper understanding of its mechanism are currently underway.

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