A Formylating Agent by Dehydration of the Natural Product DIMBOA

The natural aglucone 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA, 1) of maize underwent spontaneous dehydration and rearrangement to form 3-formyl-6-methoxybenzoxazolin-2(3H)-one (FMBOA, 2) on reaction with N-ethoxycarbonyl-trichloroacetaldimine. Compound 2 was proven to be a reactiv...

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Veröffentlicht in:	Journal of natural products (Washington, D.C.) D.C.), 1999-08, Vol.62 (8), p.1151-1153
Hauptverfasser:	Hofmann, Angelika, Sicker, Dieter
Format:	Artikel
Sprache:	eng
Schlagworte:	biochemical pathways chemical constituents of plants chemical reactions chemical structure Chemistry dehydration dimboa Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Organic chemistry plant extracts Preparations and properties spectral analysis synthesis Zea mays
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Beschreibung
Zusammenfassung:	The natural aglucone 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3(4H)-one (DIMBOA, 1) of maize underwent spontaneous dehydration and rearrangement to form 3-formyl-6-methoxybenzoxazolin-2(3H)-one (FMBOA, 2) on reaction with N-ethoxycarbonyl-trichloroacetaldimine. Compound 2 was proven to be a reactive formyl donor toward N-, O-, and S-nucleophiles, which may be important in case 2 is formed under biological conditions.
ISSN:	0163-3864 1520-6025
DOI:	10.1021/np980515s