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

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.