Synthesis and selective reactions of v‐triazolo‐[1,5‐b]pyridazinium salts with nucleophiles. A facile access to functionalized ethenyl‐1,2,3‐triazoles

Zsuzsanna Riedl, György Hajós, András Messmer, Gert Kollenz

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

v‐Triazolo[1,5‐b]pyridazinium salts 5a‐c synthesized from α‐pyridazinyl ketone arylhydrazones and 2,4,4,6‐tetrabromocyclohexa‐2,5‐dien‐1‐one (TBB) reacted selectively with nucleophiles to yield ‐ besides substituted derivatives 6 ‐ ring‐opened cyano compound 9 and/or v‐triazoles containing olefinic side chain 10–12. Mechanistic considerations reveal that cation 5 reacts with nucleophiles predominantly at C‐7 unless other positions are especially activated. This selectivity proved to be in good agreement with results of semiempirical quantum chemical calculations.

Original languageEnglish
Pages (from-to)819-823
Number of pages5
JournalJournal of Heterocyclic Chemistry
Volume30
Issue number3
DOIs
Publication statusPublished - Jan 1 1993

ASJC Scopus subject areas

  • Organic Chemistry

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