A New General Approach to the 2-Hydroxy-2H-1,4-benzoxazin-3(4H)-one Skeleton via Diisobutylaluminum Hydride Reduction of 2,3-Dioxo-1,4-benzoxazines
- 1 January 1993
- journal article
- research article
- Published by Georg Thieme Verlag KG in Synthesis
- Vol. 1993 (08) , 771-772
- https://doi.org/10.1055/s-1993-25936
Abstract
A series of naturally occurring hemiacetals 2a-d was synthesized by the chemoselective diisobutylaluminum hydride reduction of 2,3-dioxo-4H-1, 4-benzoxazines 1a,b and their N-hydroxy derivatives 1c,d precursors. The procedure described represents a new general approach to the 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one skeleton giving rise to the bioactive natural hydroxamic acids 2,4-dihydroxy-2H-1, 3(4H)-one (2c) and 2,4-dihydroxy-7-methoxy-2H-1, 4-benzoxazin-3(4H)-one (2d) in only three steps starting from nitrophenols.Keywords
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