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

Molecules. 2022 Nov 29;27(23):8319. doi: 10.3390/molecules27238319.

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: Pd cross-coupling; indanones; isoindolinones; phthalazinones.

MeSH terms

  • Cyclization
  • Indans*
  • Isoindoles* / chemistry

Substances

  • Isoindol-1-one
  • Isoindoles
  • indan
  • Indans

Grants and funding

This research received no external funding.