Synthesis of 5H-pyridazino[4,5-b]indoles and their benzofurane analogues utilizing an intramolecular Heck-type reaction

Beáta Dajka-Halász, Katrien Monsieurs, Olivér Éliás, László Károlyházy, Pál Tapolcsányi, Bert U.W. Maes, Zsuzsanna Riedl, György Hajós, Roger A. Dommisse, Guy L.F. Lemière, Janez Košmrlj, Péter Mátyus

Research output: Contribution to journalArticle

49 Citations (Scopus)

Abstract

The title ring systems were prepared from pyridazin-3(2H)-one precursors in novel, efficient pathways. 2-Methylbenzo[b]furo[2,3-d]pyridazin-1(2H)-one was synthesized via a regioselective nucleophilic substitution reaction of a 2-methyl-4,5-dihalopyridazin-3(2H)-one with phenol followed by an intramolecular Heck-type reaction. The same molecule and its 6-phenyl analogue were also prepared via reaction of 2-methyl-5-iodopyridazin-3(2H)-one or 2-methyl-5-chloro-6-phenylpyridazin-3(2H)-one, respectively, with 2-bromophenol or 2-iodophenol followed by Pd-catalyzed cyclodehydrohalogenation. Moreover, a new approach for the synthesis of 2-methyl-2,5-dihydro-1H-pyridazino[4,5-b] indol-1-ones was also elaborated utilizing a Heck-type ring closure reaction on 5-[(2-bromophenyl)amino]-2-methylpyridazin-3(2H)-ones which were obtained via Buchwald-Hartwig amination of 2-methyl-5-halopyridazin-3(2H)-ones with 2-bromoaniline.

Original languageEnglish
Pages (from-to)2283-2291
Number of pages9
JournalTetrahedron
Volume60
Issue number10
DOIs
Publication statusPublished - Mar 1 2004

Keywords

  • Aza-β-carboline
  • Buchwald-Hartwig amination
  • Intramolecular Heck-type reaction
  • Palladium
  • Pyridazinone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Synthesis of 5H-pyridazino[4,5-b]indoles and their benzofurane analogues utilizing an intramolecular Heck-type reaction'. Together they form a unique fingerprint.

  • Cite this

    Dajka-Halász, B., Monsieurs, K., Éliás, O., Károlyházy, L., Tapolcsányi, P., Maes, B. U. W., Riedl, Z., Hajós, G., Dommisse, R. A., Lemière, G. L. F., Košmrlj, J., & Mátyus, P. (2004). Synthesis of 5H-pyridazino[4,5-b]indoles and their benzofurane analogues utilizing an intramolecular Heck-type reaction. Tetrahedron, 60(10), 2283-2291. https://doi.org/10.1016/j.tet.2004.01.024