1-Oxo-2-hydroxy-1,2-dihydroacronycine: A Useful Synthon in the Acronycine Series for the Introduction of Amino Substituents at 6-Position and for the Conversion into Isopropylfuroacridones

Abstract

Thermic aromatic nucleophilic displacement of the methoxy group at C-6 of (±)-1-oxo-2-hydroxy-1,2-dihydroacronycine (2) by an amine is a reaction that gives a facile entry to acronycine derivatives bearing an amino substituent at this position. The introduction of the amino substituents was confirmed with a long-range ¹H-¹⁵N correlation NMR spectrum at natural abundance. Under basic conditions, compound 2 can also be rearranged to the corresponding isopropylfuroacridone 12, in 80% yield.