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

Zoltán Vincze, Péter Nemes, B. 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
Publication statusPublished - May 6 2004

Fingerprint

Tetrahydroisoquinolines
Pyridines
Cerium
Pyrroles
Cyclization
Aldehydes
Quinolizines
Ketones
heliamine
cerous chloride
pyrrolo(2,1-a)isoquinoline

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Cerium(III)-catalyzed cyclizations with 1-cyanomethylene tetrahydroisoquinoline : Substituent controlled formation of fused pyrroles or pyridines. / Vincze, Zoltán; Nemes, Péter; Balázs, B.; Tóth, Gábor; Scheiber, Pál.

In: Synlett, No. 6, 06.05.2004, p. 1023-1026.

Research output: Contribution to journalArticle

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T2 - Substituent controlled formation of fused pyrroles or pyridines

AU - Vincze, Zoltán

AU - Nemes, Péter

AU - Balázs, B.

AU - Tóth, Gábor

AU - Scheiber, Pál

PY - 2004/5/6

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N2 - 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.

AB - 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.

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KW - Benzo[a]quinolizines

KW - Cerium(III) chloride

KW - Cyclization

KW - Pyrrolo[2,1-a] isoquinolines

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