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

Dedicated to the memory of Prof. Kálmán Hideg

Abstract

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.

Key words

free radicals - CH functionalization - oxidation - pyrazines - protecting groups

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