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Synthesis 1993; 1993(8): 771-772
DOI: 10.1055/s-1993-25936
short paper
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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

Dieter Sicker* , Holger Hartenstein
  • *Institut für Organische Chemie der Universität Leipzig, Talstr. 35, D-(O)7010 Leipzig, Germany
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Publication Date:
27 September 2002 (online)

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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.