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Biomimetic synthesis of 4-acetylbenzoxazolin-2(3H)-one isolated from Zea mays

✍ Scribed by Carlos A. Escobar; Michael Kluge; Dieter Sicker


Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
589 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

4‐Acetylbenzoxazolin‐2(3__H__)‐one has been prepared biomimetically during attempts to synthesize the hemiacetalic hydroxamic acid 5‐acetyl‐2,4‐dihydroxy‐2__H__‐1,4‐benzoxazin‐3(4__H__)‐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(3__H__)‐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(4__H__)‐one which in turn could have been enzymatically released by a β‐glucosidase from the corresponding 2‐β‐D‐glucoside.


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