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

doi:10.1055/s-0030-1260219

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

Research output: Contribution to journal › Article

11 Citations (Scopus)

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 language	English
Article number	Z64411SS
Pages (from-to)	3371-3374
Number of pages	4
Journal	Synthesis
Issue number	20
DOIs	https://doi.org/10.1055/s-0030-1260219
Publication status	Published - Sep 12 2011
Externally published	Yes

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Keywords

alkynes
annulation
hydrazides
isoquinolines
silver catalysis
ylides

ASJC Scopus subject areas

Catalysis
Organic Chemistry

Cite this

Peshkov, V. A., Pereshivko, O. P., Vanhove, S., Ermolatev, D. S., & Vandereycken, E. V. (2011). Synthesis of isoquinolinium-2-yl amides via silver(I)-catalyzed ring closure of N′-(2-alkynylbenzylidene)hydrazides. Synthesis, (20), 3371-3374. [Z64411SS]. https://doi.org/10.1055/s-0030-1260219

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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.",

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AU - Pereshivko, Olga P.

AU - Vanhove, Sofie

AU - Ermolatev, Denis S.

AU - Vandereycken, Erik V.

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10.1055/s-0030-1260219