A facile synthesis of 1,2,4-triazine fused pyrroline nitroxides as useful paramagnetic building block

Mohsen, Yafea and Bognár, Balázs and Jekö, József and Bényei, Attila Csaba and Kálai, Tamás (2026) A facile synthesis of 1,2,4-triazine fused pyrroline nitroxides as useful paramagnetic building block. RESULTS IN CHEMISTRY, 30. No. 103779. ISSN 2211-7156 (In Press)

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Abstract

In this study, we report an efficient synthesis of 3-amino- or 3-methylsulfanyl-6-oxyl-pyrrolo[3,4-e][1,2,4] triazine radical from O-methyl protected 3,4-dioxopyrrolidine pre-nitroxide. From the amino derivative, the corresponding 3-iodo-6-oxyl-pyrrolo[3,4-e][1,2,4]triazine radical was obtained via radical substitution. This compound was an excellent substrate for Pd-catalyzed cross-coupling reactions. The oxidation of O-methyl protected 3-methylsulfanyl-pyrrolo[3,4-e][1,2,4]triazine with excess amount of 3-chloroperbenzoic acid afforded a 3- methylsulfonyl-6-oxyl-pyrrolo[3,4-e][1,2,4]triazine radical that could be used in aromatic nucleophilic substitution reactions to produce new paramagnetically modified amino acids and polycyclic compounds via an intramolecular Diels-Alder reaction.

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