Is samoquasine A indeed benzo[f]phthalazin-4(3H)-one? Unambiguous, straightforward synthesis of benzo[f]phthalazin-4(3H)-one and its regioisomer benzo[f]phthalazin-1(2H)-one

Katrien Monsieurs, Pál Tapolcsányi, Kristof T.J. Loones, Gábor Neumajer, J. A. Dirk De Ridder, Kees Goubitz, Guy L.F. Lemière, Roger A. Dommisse, Péter Mátyus, Bert U.W. Maes

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

In search for the structural elucidation of samoquasine A, a natural product isolated from the seeds of Annona squamosa L., two benzo[f]phthalazinone isomers have been synthesized. The synthetic pathway followed to build up these skeletons is based on the combination of two Suzuki reactions on a pyridazinone precursor and a ring closure reaction via a condensation reaction. 1H NMR data of the synthesized compound allowed to establish that the structure of the natural product samoquasine A is not benzo[f]phthalazin-4(3H)-one, as previously suggested.

Original languageEnglish
Pages (from-to)3870-3881
Number of pages12
JournalTetrahedron
Volume63
Issue number18
DOIs
Publication statusPublished - Apr 30 2007

Keywords

  • Benzophthalazine
  • Condensation
  • Natural product
  • Suzuki reaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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