ASPERGILLIC acid is a pyrazine cyclic hydroxamic acid of structure (I). Although a general method has been developed for the synthesis of pyridine and quinoline cyclic hydroxamic acids1, attempts to apply this method in order to effect a synthesis of a pyrazine cyclic hydroxamic acid have been unsuccessful, peroxidation of a 2-substituted pyrazine giving the 4-oxide and not the required 1-oxide2. We now describe two syntheses of pyrazine cyclic hydroxamic acids starting from α-aminohydroxamic acids (II), which are readily obtained by the action of hydroxylamine on αamino-esters.
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DUNN, G., ELVIDGE, J., NEWBOLD, G. et al. Synthesis of Pyrazine Cyclic Hydroxamic Acids Related to Aspergillic Acid. Nature 164, 181 (1949). https://doi.org/10.1038/164181a0
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