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

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

Fingerprint

Amides
Silver
Trifluoroacetic Acid

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Synthesis of isoquinolinium-2-yl amides via silver(I)-catalyzed ring closure of N′-(2-alkynylbenzylidene)hydrazides. / Peshkov, Vsevolod A.; Pereshivko, Olga P.; Vanhove, Sofie; Ermolatev, Denis S.; Vandereycken, Erik V.

In: Synthesis, No. 20, Z64411SS, 12.09.2011, p. 3371-3374.

Research output: Contribution to journal › Article

Peshkov, VA, Pereshivko, OP, Vanhove, S, Ermolatev, DS & Vandereycken, EV 2011, 'Synthesis of isoquinolinium-2-yl amides via silver(I)-catalyzed ring closure of N′-(2-alkynylbenzylidene)hydrazides', Synthesis, no. 20, Z64411SS, pp. 3371-3374. https://doi.org/10.1055/s-0030-1260219
Peshkov VA, Pereshivko OP, Vanhove S, Ermolatev DS, Vandereycken EV. Synthesis of isoquinolinium-2-yl amides via silver(I)-catalyzed ring closure of N′-(2-alkynylbenzylidene)hydrazides. Synthesis. 2011 Sep 12;(20):3371-3374. Z64411SS. https://doi.org/10.1055/s-0030-1260219
Peshkov, Vsevolod A. ; Pereshivko, Olga P. ; Vanhove, Sofie ; Ermolatev, Denis S. ; Vandereycken, Erik V. / Synthesis of isoquinolinium-2-yl amides via silver(I)-catalyzed ring closure of N′-(2-alkynylbenzylidene)hydrazides. In: Synthesis. 2011 ; No. 20. pp. 3371-3374.
@article{a1668a4d211f4acf8c2442686253422a,
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",
month = "9",
day = "12",
doi = "10.1055/s-0030-1260219",
language = "English",
pages = "3371--3374",
journal = "Synthesis",
issn = "0039-7881",
publisher = "Georg Thieme Verlag",
number = "20",

}

TY - JOUR

T1 - Synthesis of isoquinolinium-2-yl amides via silver(I)-catalyzed ring closure of N′-(2-alkynylbenzylidene)hydrazides

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

N2 - 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.

AB - 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.

KW - alkynes

KW - annulation

KW - hydrazides

KW - isoquinolines

KW - silver catalysis

KW - ylides

UR - http://www.scopus.com/inward/record.url?scp=80053911687&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=80053911687&partnerID=8YFLogxK

U2 - 10.1055/s-0030-1260219

DO - 10.1055/s-0030-1260219

M3 - Article

SP - 3371

EP - 3374

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 20

M1 - Z64411SS

ER -

Access to Document