TY - JOUR

T1 - Oxidative Coupling of Guanidines and Isocyanides Under Nickel(II) Catalysis: An Access to Imidazoline Derivatives with Antibacterial Activity

AU - Гаврилов, Георгий Александрович

AU - Нгуен, Туан Киет

AU - Каткова, Светлана Александровна

AU - Ростовский, Николай Витальевич

AU - Рогачёва, Елизавета

AU - Краева, Людмила Александровна

AU - Кинжалов, Михаил Андреевич

PY - 2025/2/2

Y1 - 2025/2/2

N2 - A novel and concise approach to rare 2,3,5-triamino-imidazole scaffolds via Ni-catalyzed coupling of alkylisocyanides and N,N′-diarylguanidines has been developed. This reaction features include mild conditions (thermal or visible light activation), a wide substrate scope, and high efficiency. The coupling proceeds through a NiII/NiIV catalytic cycle, involving two-electron aerobic oxidation and the sequential insertion of two isocyanide units into Ni−N bonds.Testing these compounds against pathogens of the ESKAPE panel showed their high activity with a minimum inhibitory concentration down to 0.38 μg/mL.

AB - A novel and concise approach to rare 2,3,5-triamino-imidazole scaffolds via Ni-catalyzed coupling of alkylisocyanides and N,N′-diarylguanidines has been developed. This reaction features include mild conditions (thermal or visible light activation), a wide substrate scope, and high efficiency. The coupling proceeds through a NiII/NiIV catalytic cycle, involving two-electron aerobic oxidation and the sequential insertion of two isocyanide units into Ni−N bonds.Testing these compounds against pathogens of the ESKAPE panel showed their high activity with a minimum inhibitory concentration down to 0.38 μg/mL.

KW - antibacterial activity

KW - imidazole

KW - isocyanide• nickel catalysis

UR - https://www.mendeley.com/catalogue/ce9aae03-43e4-3e47-8ce8-48c767a40cfd/

U2 - 10.1002/cmdc.202400904

DO - 10.1002/cmdc.202400904

M3 - Article

JO - Farmaco

JF - Farmaco

SN - 1860-7179

M1 - e202400904

ER -