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

Carlos A. Escobar, Michael Kluge, Dieter Sicker

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one (8), the hitherto undescribed free hemiacetatic aglycone of a benzoxazinoid acetal glucoside 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 glucoside is by methoxide elimination a precursor to form a multi-centered electrophile that was recently reported to be the bioactive principle of the benzoxazinoid lead.

Original languageEnglish
Pages (from-to)1017-1020
Number of pages4
JournalTetrahedron Letters
Volume38
Issue number6
DOIs
Publication statusPublished - 10 Feb 1997

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Syntheses of 2-Hydroxy-4,7-dimethoxy-2H-1,4-benzoxazin-3(4H)-one: A precursor of a bioactive electrophile from Gramineae'. Together they form a unique fingerprint.

Cite this