A mechanistic dehydration study with [2-(13)C]-DIMBOA.

Abstract

Dehydration of a 2-(13)C-labeled synthetic sample of the natural aglucone 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one ([2-(13)C]-DIMBOA, 10) using N-ethoxycarbonyltrichloroacetaldimine led to 3-formyl-6-methoxybenzoxazolin-2(3H)-one ((13)C-labeled FMBOA, 11) with complete transfer of the (13)C label into the -CHO group. On the basis of this finding, a mechanism for the dehydration is proposed.

• Authors: Huang Hao, Joachim Sieler, Dieter Sicker
• Journal: Journal of natural products (J Nat Prod) Vol. 65 Issue 4 Pg. 466-9 (Apr 2002) ISSN: 0163-3864 [Print] United States
• PMID: 11975481 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• 3-formyl-6-methoxybenzoxazolin-2(3H)-one
• Benzoxazines
• Benzoxazoles
• Carbon Isotopes
• Glycolates
• Oxazines
• glycolic acid
• 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one

Topics

• Benzoxazines
• Benzoxazoles (chemistry)
• Carbon Isotopes (chemistry)
• Dehydration
• Glycolates (chemistry)
• Isotope Labeling
• Molecular Conformation
• Molecular Structure
• Nuclear Magnetic Resonance, Biomolecular
• Oxazines (chemistry)