Reactions of 3-Hydroxy-2-phenyl-1<i>H</i>-benzo[<i>e</i>]isoindol-1-one: A Route to 3-Hydroxy-/3-anilinobenzo[<i>e</i>]indan-1-ones and Benzo[<i>f</i>]phthalazin-1(2<i>H</i>)-ones

Abstract

New hydroxy- and anilinoindanone derivatives 3 and 4 were synthesized starting from 3-hydroxybenzo[e]isoindolinone 1 via the addition of alkyllithium (s-BuLi, n-BuLi, MeLi or i-PrLi) to the carbonyl group, followed by lactam ring opening and, finally, an intramolecular cyclization leading to target compounds. The same starting material was used for the preparation of the new benzo[f]phthalazinone derivatives 12–16 through multi-step reactions. The target derivative 16 was obtained from the corresponding bromolactam 15 by the Buchwald–Hartwig amination. Structures of the obtained compounds were confirmed by the NMR spectra.

Keywords

• indanones
• isoindolinones
• Pd cross-coupling
• phthalazinones