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

Huang Hao·Joachim Sieler·Dieter Sicker
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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.

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BenzoxazinesBenzoxazolesCarbon IsotopesDehydrationGlycolatesIsotope LabelingMolecular ConformationMolecular StructureNuclear Magnetic Resonance, BiomolecularOxazinesJournal ArticleResearch Support, Non-U.S. Gov't

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Huang Hao, Joachim Sieler, Dieter Sicker. 2002. A mechanistic dehydration study with [2-(13)C]-DIMBOA.. https://doi.org/10.1021/np0102455

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