Synthesis of the dibenzo[f,h]phthalazine and dibenzo[f,h]cinnoline skeleton via a 'Suzuki-Pd-catalyzed intramolecular arylation' and a 'Suzuki-Pschorr' approach

P. Tapolcsányi, Bert U W Maes, Katrien Monsieurs, Guy L F Lemière, Z. Riedl, G. Hajós, Bart Van Den Driessche, Roger A. Dommisse, P. Mátyus

Research output: Contribution to journalArticle

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Abstract

Palladium-catalyzed intramolecular arylation of 2-benzyl-5-(2-bromophenyl)-4-phenylpyridazin-3(2H)-one yielded hitherto unknown 2-benzyldibenzo[f,h]phthalazin-1(2H)-one. The synthesis of this new tetracyclic pyridazinone from 2-benzyl-5-(2-aminophenyl)-4-phenylpyridazin-3(2H)-one via a Pschorr type reaction was also investigated. Similarly, the construction of 2-methyldibenzo[f,h]cinnolin-3(2H)-one from 2-methyl-5-(2-bromophenyl)-6-phenylpyridazin-3(2H)-one and 2-methyl-5-(2-aminophenyl)-6-phenylpyridazin-3(2H)-one is also reported. Removal of the N-benzyl protective group of 2-benzyl-dibenzo[f,h]phthalazin-1(2H)-one with AlCl3 yielded unsubstituted dibenzo[f,h]phthalazin-1(2H)-one.

Original languageEnglish
Pages (from-to)5919-5926
Number of pages8
JournalTetrahedron
Volume59
Issue number31
DOIs
Publication statusPublished - Jul 28 2003

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Palladium
Skeleton
aluminum chloride
cinnoline
phthalazine

Keywords

  • Intramolecular arylation
  • Palladium
  • Pschorr reaction
  • Pyridazinone
  • Suzuki reaction

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of the dibenzo[f,h]phthalazine and dibenzo[f,h]cinnoline skeleton via a 'Suzuki-Pd-catalyzed intramolecular arylation' and a 'Suzuki-Pschorr' approach. / Tapolcsányi, P.; Maes, Bert U W; Monsieurs, Katrien; Lemière, Guy L F; Riedl, Z.; Hajós, G.; Van Den Driessche, Bart; Dommisse, Roger A.; Mátyus, P.

In: Tetrahedron, Vol. 59, No. 31, 28.07.2003, p. 5919-5926.

Research output: Contribution to journalArticle

Tapolcsányi, P. ; Maes, Bert U W ; Monsieurs, Katrien ; Lemière, Guy L F ; Riedl, Z. ; Hajós, G. ; Van Den Driessche, Bart ; Dommisse, Roger A. ; Mátyus, P. / Synthesis of the dibenzo[f,h]phthalazine and dibenzo[f,h]cinnoline skeleton via a 'Suzuki-Pd-catalyzed intramolecular arylation' and a 'Suzuki-Pschorr' approach. In: Tetrahedron. 2003 ; Vol. 59, No. 31. pp. 5919-5926.
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abstract = "Palladium-catalyzed intramolecular arylation of 2-benzyl-5-(2-bromophenyl)-4-phenylpyridazin-3(2H)-one yielded hitherto unknown 2-benzyldibenzo[f,h]phthalazin-1(2H)-one. The synthesis of this new tetracyclic pyridazinone from 2-benzyl-5-(2-aminophenyl)-4-phenylpyridazin-3(2H)-one via a Pschorr type reaction was also investigated. Similarly, the construction of 2-methyldibenzo[f,h]cinnolin-3(2H)-one from 2-methyl-5-(2-bromophenyl)-6-phenylpyridazin-3(2H)-one and 2-methyl-5-(2-aminophenyl)-6-phenylpyridazin-3(2H)-one is also reported. Removal of the N-benzyl protective group of 2-benzyl-dibenzo[f,h]phthalazin-1(2H)-one with AlCl3 yielded unsubstituted dibenzo[f,h]phthalazin-1(2H)-one.",
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AU - Van Den Driessche, Bart

AU - Dommisse, Roger A.

AU - Mátyus, P.

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