Novel Thermal Rearrangement of Fused Diaryl-v-Triazolium Salts to Neutral Indazole Derivatives. Fused Azolium Salts

T. Soós, Gy Hajós, A. Messmer

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Alkylation of 1,3-diaryl-v-triazolo[1,5-a]benzimidazole (1) by trimethyloxonium salt afforded selectively the 4-methyl quaternary salt 2, whereas reaction with dimethyl sulfate at elevated temperature resulted in ring transformation, implying ring opening to a nitrenium cation and a subsequent electrophilic ring closure to give a benzimidazolylindazole product 5. Independent of the methylation, a similar easy thermal rearrangement was observed with alkylated 1,3-diaryl-v-triazolo[1,5-α]benzimidazolium (2 → 4) and the related benzothiazolium salt (7 → 8). Extension of the reaction to diaryl-v-triazolopyridinium salt (9 → 10 + 11) allowed observation of an additional novel reaction path that provided further support for the supposed reaction mechanism.

Original languageEnglish
Pages (from-to)1136-1138
Number of pages3
JournalJournal of Organic Chemistry
Volume62
Issue number4
Publication statusPublished - Dec 1 1997

ASJC Scopus subject areas

  • Organic Chemistry

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