A mechanistic dehydration study with [2-(13)C]-DIMBOA.
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.
Hao
Huang
H
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, People's Republic of China.
Sieler
Joachim
J
Sicker
Dieter
D
D048588:Benzoxazines; D001583:Benzoxazoles / Q000737:chemistry*; D002247:Carbon Isotopes / Q000737:chemistry; D003681:Dehydration; D006016:Glycolates / Q000737:chemistry; D007553:Isotope Labeling; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010078:Oxazines / Q000737:chemistry*
C455168:3-formyl-6-methoxybenzoxazolin-2(3H)-one; D048588:Benzoxazines; D001583:Benzoxazoles; D002247:Carbon Isotopes; D006016:Glycolates; D010078:Oxazines; C031149:glycolic acid; C050733:2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one