Synthesis of Pyrazine Cyclic Hydroxamic Acids Related to Aspergillic Acid

Abstract

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.

References

  1. 1

    Newbold and Spring, J. Chem. Soc., 1864 (1948).

  2. 2

    Baxter, Newbold and Spring, J. Chem. Soc., 1859 (1948).

  3. 3

    Jones, J. Amer. Chem. Soc., 71, 78 (1949).

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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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