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
No coin nor oath required. For personal study only.
✦ 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.
📜 SIMILAR VOLUMES
## Abstract Synthesis of the linear and angular furoquinolin‐4‐one derivatives 6 and 12 was performed, using nitrobenzofurans 3 and 9 as key intermediates. These compounds were reduced to the corresponding aminobenzofurans 4 and 10, which were condensed in two steps to yield, the linear furoquinoli