Mild and rapid method for the generation of ortho-(naphtho)quinone methide intermediates.
A new mild method has been devised for generating o-(naphtho)quinone methides via fluoride-induced desilylation of silyl derivatives of o-hydroxybenzyl(or 1-naphthylmethyl) nitrate. The reactive o-(naphtho)quinone methide intermediates were trapped by C, O, N, and S nucleophiles and underwent "inverse electron-demand" hetero-Diels-Alder reaction with dienophiles to give stable adducts. The method has useful potential application in natural product synthesis and drug research.
Department of Chemistry, University of Ioannina, Section of Organic Chemistry and Biochemistry, 451 10 Ioannina, Greece.
Abdul kadar
Ak
Shaikh
Alexander J A
AJ
Cobb
George
G
Varvounis
D019281:Dimerization; D045563:Indolequinones / Q000138:chemical synthesis*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis*; D013997:Time Factors
D045563:Indolequinones; D009285:Naphthoquinones; C068040:quinone methide