A novel one-pot, three-component access to hexahydropyrrolo[2,1-a] isoquinolines by an alkylation-dehydrohalogenation-1,3-dipolar cycloaddition sequence

Miklós Nyerges, Barbara Somfai, J. Tóth, L. Tőke, András Dancsó, Gábor Blaskó

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

A simple one-pot process for the alkylation of isoquinolines followed by a dehydrohalogenation of the quaternary salts formed and by an in situ trapping of azomethine ylides with appropriate dipolarophiles is described. This method has successfully been applied to the synthesis of benz[5,6]azepino[2,1-a] isoquinolines and 5,6-dihydroindazolo[3,2-a]isoquinoline 8-oxides via an 1,7-electrocyclization process of similar type azomethine ylides.

Original languageEnglish
Pages (from-to)2039-2045
Number of pages7
JournalSynthesis
Issue number12
DOIs
Publication statusPublished - Aug 1 2005

Fingerprint

Isoquinolines
Cycloaddition
Alkylation
Salts
Oxides
azomethine

Keywords

  • Cycloadditions
  • Electrocyclic reactions
  • Heterocycles
  • Tandem reactions
  • Ylides

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A novel one-pot, three-component access to hexahydropyrrolo[2,1-a] isoquinolines by an alkylation-dehydrohalogenation-1,3-dipolar cycloaddition sequence. / Nyerges, Miklós; Somfai, Barbara; Tóth, J.; Tőke, L.; Dancsó, András; Blaskó, Gábor.

In: Synthesis, No. 12, 01.08.2005, p. 2039-2045.

Research output: Contribution to journalArticle

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AU - Somfai, Barbara

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AU - Dancsó, András

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