Cerium(III)-catalyzed cyclizations with 1-cyanomethylene tetrahydroisoquinoline: Substituent controlled formation of fused pyrroles or pyridines

Zoltán Vincze, Péter Nemes, Barbara Balázs, Gábor Tóth, Pál Scheiber

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

1-Cyanomethylene-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline reacts with α,β-unsaturated aldehydes and ketones in presence of cerium(III) chloride, to yield benzo[a]quinolizines. α-Alkyl substituted unsaturated aldehydes under the same conditions, however, afford pyrrolo[2,1-a] isoquinolines.

Original languageEnglish
Pages (from-to)1023-1026
Number of pages4
JournalSynlett
Issue number6
DOIs
Publication statusPublished - May 6 2004

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Keywords

  • Benzo[a]quinolizines
  • Cerium(III) chloride
  • Cyclization
  • Pyrrolo[2,1-a] isoquinolines
  • β-enaminonitrile

ASJC Scopus subject areas

  • Organic Chemistry

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