Vanadium-catalyzed Hydration of 2-Cyanopyrazine to Pyrazinamide with Unique Substrate Specificity

Chem Asian J. 2023 Nov 16;18(22):e202300741. doi: 10.1002/asia.202300741. Epub 2023 Oct 12.

Abstract

Pyrazinamide is an important medicine used for the treatment of tuberculosis(TB). The preparation of pyrazinamide via catalytic hydration of 2-cyanopyrazine is of great economic interest with high atomic economy. Heterogeneous non-precious transition metal-catalyzed hydration of nitriles under neutral reaction conditions would be rather attractive. Herein vanadium-nitrogen-carbon materials were fabricated and employed for selective hydration of nitriles using water as both the solvent and reactant. 2-Cyanopyrazine could be smoothly converted into to pyrazinamide with unique substrate specificity. Additives with different N and O atoms could significantly affect hydration of 2-cyanopyrazine due to competitive adsorption/coordination in the reaction system. This work provides a new approach for non-precious metal catalyzed hydration of nitriles.

Keywords: Amide; Hydration; Nitrile; Substrate specificity; Vanadium.