Biomimetic Synthesis of 4-Acetylbenzoxazolin-2(3H)-one Isolated from Zea mays

Article abstract of DOI:10.1002/jhet.5570340506

4-Acctylbenzoxazolin-2(3H)-one has been prepared biomimetically during attempts to synthesize the hemiacetalic hydroxamic acid 5-acetyl-2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one by the immediate degradation of this unstable compound generated as an intermediate. Thus, 4-acetylbenzoxazolin-2(3H)one recently isolated from Zea mays kernels, and similar to other benzoxazolin-2(3H)-ones known from plant sources, is assumed to have originated from the degradation of natural 5-acetyl-2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one which in turn could have been enzymatically released by a β-glucosidase from the corresponding 2-β-D-glucoside.