Iodine (III)-mediated generation of nitrogen-tethered orthoquinol acetates for the construction of oxygenated indole, quinoline, and phenanthridine alkaloid motifs

L Pouységu, AV Avellan, S Quideau

文献索引：Pouysegu, Laurent; Avellan, Anne-Virginie; Quideau, Stephane Journal of Organic Chemistry, 2002 , vol. 67, # 10 p. 3425 - 3436

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被引用次数: 54

摘要

Functionalized indole and quinoline derivatives are conveniently prepared from nitrogen- tethered 2-methoxyphenols via phenyliodine (III) diacetate mediated oxidative acetoxylation, followed by a fluoride-or base-induced intramolecular nucleophilic addition reaction. This regioselective Michael-type addition step is further discussed in view of the rearrangement of orthoquinol acetate intermediates into paraquinol acetates that is sometimes observed ...