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

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Biological Products
Annona
Condensation reactions
Skeleton
Isomers
Seed
Seeds
Nuclear magnetic resonance
perlolidine
Proton Magnetic Resonance Spectroscopy

Keywords

  • Benzophthalazine
  • Condensation
  • Natural product
  • Suzuki reaction

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

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

In: Tetrahedron, Vol. 63, No. 18, 30.04.2007, p. 3870-3881.

Research output: Contribution to journalArticle

Monsieurs, Katrien ; Tapolcsányi, Pál ; Loones, Kristof T J ; Neumajer, Gábor ; Dirk De Ridder, J. A. ; Goubitz, Kees ; Lemière, Guy L F ; Dommisse, Roger A. ; Mátyus, Péter ; Maes, Bert U W. / 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. In: Tetrahedron. 2007 ; Vol. 63, No. 18. pp. 3870-3881.
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