Synthesis of isoquinolinium-2-yl amides via silver(I)-catalyzed ring closure of N′-(2-alkynylbenzylidene)hydrazides

Vsevolod A. Peshkov, Olga P. Pereshivko, Sofie Vanhove, Denis S. Ermolatev, Erik V. Vandereycken

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Abstract

An efficient one-pot protocol for the synthesis of isoquinolinium-2-yl amides starting from readily available hydrazides and 2-alkynylbenzaldehydes is described. The key step of the protocol is a silver(I)-catalyzed ring-closure of N-(2-alkynylbenzylidene)hydrazides that are generated in situ. Isoquinolinium-2-yl amides derived from tert-butoxycarbonyl hydrazide could be further deprotected, delivering 2-aminoisoquinolinium trifluoroacetates.

Original languageEnglish
Article numberZ64411SS
Pages (from-to)3371-3374
Number of pages4
JournalSynthesis
Issue number20
DOIs
Publication statusPublished - Sep 12 2011
Externally publishedYes

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Keywords

  • alkynes
  • annulation
  • hydrazides
  • isoquinolines
  • silver catalysis
  • ylides

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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