Syntheses of 2-hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one: A precursor of a bioactive electrophile from Gramineae

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

• Book ID: 104256237
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 225 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02492-6

✦ Synopsis

2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one (8), the hitherto undescribed free hemiacetalic agiyeone of a benzoxazinoid acetal glucnside naturally occurring in wheat, has been synthesized following two pathways, independently. This cyclic hydroxamic acid methyl ester proved to be very unstable when in solution. This gives rise to the assumption that HDIBOA naturally released from its acetal giuco6ide is by methoxide elimination a precursor to form a multi-centered eleetrophile that was recently reported to be the binaetive principle of the benzoxazinoid lead.