A recently recognized ambident reactivity of 2,3-diamino-isoquinolinium salts

Z. Riedl, László Filák, O. Egyed, G. Hajós

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Reinvestigation of an old experimental finding - the formation of linearly fused tetrazoloisoquinolines from 2,3-diamino-isoquinolinium salts, by using 15N-labeling and 15N-NMR spectroscopy, revealed that the ring closure pathway - unlike a recently observed cyclization of the same diamino salt - does not proceed via a rearrangement route. By comparison of this reaction with the entirely different reactivities of other related 1,2-diamino-azinium salts, a general mechanism is suggested, revealing an ambident reactivity of these diamino compounds.

Original languageEnglish
Pages (from-to)158-166
Number of pages9
JournalArkivoc
Volume2009
Issue number6
Publication statusPublished - Feb 25 2009

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Salts
Cyclization
Labeling
Nuclear magnetic resonance spectroscopy

Keywords

  • N-labeling
  • N-NMR spectroscopy
  • Ambident reactivity
  • Azide-tetrazole equilibrium
  • Deamination reaction
  • Ring closure

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

A recently recognized ambident reactivity of 2,3-diamino-isoquinolinium salts. / Riedl, Z.; Filák, László; Egyed, O.; Hajós, G.

In: Arkivoc, Vol. 2009, No. 6, 25.02.2009, p. 158-166.

Research output: Contribution to journalArticle

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