1,3-dipolar cycloaddition of 3,4-dihydro-6,7-dimethoxyisoquinoline-N- methoxycarbonyl methylide with Schiff bases

Áron Szöllosy, Thomas Tischer, István Kádas, László Toke, Gábor Tóth

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

1,3-Dipolar cycloaddition of 3,4-dihydro-6,7-dimethoxyisoquinoline-N- methoxycarbonyl methylide to Schiff bases results in the imidazo[2,1- a]isoquinolines as single racemates. The cycloadducts obtained are exo isomers, with one exception. The only compound with endo structure isomerized via cycloreversion followed by cycloaddition to the thermodynamically stable exo isomer. Structural assignment of the products was achieved by comprehensive two-dimensional NMR methods. Both the exo and endo isomers exist in a trans mutually implies cis-1 mutually implies cis-2 conformational equilibrium.

Original languageEnglish
Pages (from-to)7279-7288
Number of pages10
JournalTetrahedron
Volume55
Issue number23
DOIs
Publication statusPublished - Jun 4 1999

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Keywords

  • Cycloadditions
  • Imines
  • NMR
  • Stereochemistry

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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