Selective ring opening of linearly and angularly fused triazolium salts

András Kotschy, György Hajós, András Messmer, Gurnos Jones

Research output: Article

14 Citations (Scopus)

Abstract

Angularly and linearly fused, 1,2-, and 1,3-disubstituted [1,2,4]triazolium salts were synthesized and reacted with nucleophiles. The sites of attack were found to depend both on the type of annelation and substitution pattern: the linearly fused derivative reacted at the pyridine moiety, whereas the angularly condensed salts were attacked at one of the carbon atoms of the triazole ring, and subsequent ring openings occurred in both cases. For the experienced ambident reactivity a general mechanistic scheme was proposed and the annelation-dependent regioselectivity was rationalised on the basis of an MO approach.

Original languageEnglish
Pages (from-to)1399-1410
Number of pages12
JournalTetrahedron
Volume52
Issue number4
DOIs
Publication statusPublished - jan. 1996

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Selective ring opening of linearly and angularly fused triazolium salts'. Together they form a unique fingerprint.

  • Cite this