Syntheses of Pyrazine-, Quinoxaline-, and Imidazole-Fused Pyrroline Nitroxides

Mostafa Isbera, Balázs Bognár, Gergely Gulyás-Fekete, Krisztina Kish, Tamás Kálai
2019 Synthesis (Stuttgart)  
A synthesis of a new diamagnetic synthon, 1-methoxy-2,2,5,5-tetramethylpyrrolidine-3,4-dione, was developed. Condensation of this compound with aliphatic or aromatic 1,2-diamines followed by deprotection yielded pyrroline nitroxide-fused pyrazines, pteridines, or quinoxalines, demonstrated on 7 examples in 15–39% overall yield over 2 or 3 steps. Reaction of the diamagnetic 1,2-diketone with an aldehyde and ammonium acetate produced a pyrrolo[3,4-d]imidazole scaffold in the Debus–Radziszewski reaction.
doi:10.1055/s-0039-1690678 fatcat:72uzrx3zyvclhefis2rwq5mshu