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 › peer-review

14 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

Keywords

alkynes
annulation
hydrazides
isoquinolines
silver catalysis
ylides

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1055/s-0030-1260219

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

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.",

keywords = "alkynes, annulation, hydrazides, isoquinolines, silver catalysis, ylides",

author = "Peshkov, {Vsevolod A.} and Pereshivko, {Olga P.} and Sofie Vanhove and Ermolatev, {Denis S.} and Vandereycken, {Erik V.}",

year = "2011",

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doi = "10.1055/s-0030-1260219",

language = "English",

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AU - Peshkov, Vsevolod A.

AU - Pereshivko, Olga P.

AU - Vanhove, Sofie

AU - Ermolatev, Denis S.

AU - Vandereycken, Erik V.

PY - 2011/9/12

Y1 - 2011/9/12

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KW - alkynes

KW - annulation

KW - hydrazides

KW - isoquinolines

KW - silver catalysis

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