Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles

Olga P. Pereshivko; Vsevolod A. Peshkov; Denis S. Ermolatev; Sofie Van Hove; Kristof Van Hecke; Luc Van Meervelt; Erik V. Van Der Eycken

doi:10.1055/s-0030-1260012

Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles

Olga P. Pereshivko, Vsevolod A. Peshkov, Denis S. Ermolatev, Sofie Van Hove, Kristof Van Hecke, Luc Van Meervelt, Erik V. Van Der Eycken

Research output: Contribution to journal › Article › peer-review

16 Citations (Scopus)

Abstract

A diversity-oriented protocol giving access to a novel class of spiro-cyclic guanidine derivatives is described. The copper(I)-catalyzed, three-component coupling of a ketone, an alkyne and a primary amine (KA ²-coupling) provides the required secondary propargylamines and assures the generation of diversity. The key step of the protocol, a silver(I)-mediated tandem guanylation of secondary propargylamines followed by an intramolecular heterocyclization, provides the target bis-Boc-protected-2- iminoimidazolines spiro-fused with a five-, six- or seven-membered (heterocyclic) ring, which could, in most cases, be further deprotected to the spiro-2-aminoimidazoles.

Original language	English
Article number	Z21611SS
Pages (from-to)	1587-1594
Number of pages	8
Journal	Synthesis
Issue number	10
DOIs	https://doi.org/10.1055/s-0030-1260012
Publication status	Published - May 16 2011
Externally published	Yes

Keywords

2-aminoimidazoles
ring closure
silver
spiro compounds
tandem reaction

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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title = "Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles",

abstract = "A diversity-oriented protocol giving access to a novel class of spiro-cyclic guanidine derivatives is described. The copper(I)-catalyzed, three-component coupling of a ketone, an alkyne and a primary amine (KA 2-coupling) provides the required secondary propargylamines and assures the generation of diversity. The key step of the protocol, a silver(I)-mediated tandem guanylation of secondary propargylamines followed by an intramolecular heterocyclization, provides the target bis-Boc-protected-2- iminoimidazolines spiro-fused with a five-, six- or seven-membered (heterocyclic) ring, which could, in most cases, be further deprotected to the spiro-2-aminoimidazoles.",

keywords = "2-aminoimidazoles, ring closure, silver, spiro compounds, tandem reaction",

author = "Pereshivko, {Olga P.} and Peshkov, {Vsevolod A.} and Ermolatev, {Denis S.} and {Van Hove}, Sofie and {Van Hecke}, Kristof and {Van Meervelt}, Luc and {Van Der Eycken}, {Erik V.}",

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doi = "10.1055/s-0030-1260012",

language = "English",

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T1 - Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles

AU - Pereshivko, Olga P.

AU - Peshkov, Vsevolod A.

AU - Ermolatev, Denis S.

AU - Van Hove, Sofie

AU - Van Hecke, Kristof

AU - Van Meervelt, Luc

AU - Van Der Eycken, Erik V.

PY - 2011/5/16

Y1 - 2011/5/16

N2 - A diversity-oriented protocol giving access to a novel class of spiro-cyclic guanidine derivatives is described. The copper(I)-catalyzed, three-component coupling of a ketone, an alkyne and a primary amine (KA 2-coupling) provides the required secondary propargylamines and assures the generation of diversity. The key step of the protocol, a silver(I)-mediated tandem guanylation of secondary propargylamines followed by an intramolecular heterocyclization, provides the target bis-Boc-protected-2- iminoimidazolines spiro-fused with a five-, six- or seven-membered (heterocyclic) ring, which could, in most cases, be further deprotected to the spiro-2-aminoimidazoles.

AB - A diversity-oriented protocol giving access to a novel class of spiro-cyclic guanidine derivatives is described. The copper(I)-catalyzed, three-component coupling of a ketone, an alkyne and a primary amine (KA 2-coupling) provides the required secondary propargylamines and assures the generation of diversity. The key step of the protocol, a silver(I)-mediated tandem guanylation of secondary propargylamines followed by an intramolecular heterocyclization, provides the target bis-Boc-protected-2- iminoimidazolines spiro-fused with a five-, six- or seven-membered (heterocyclic) ring, which could, in most cases, be further deprotected to the spiro-2-aminoimidazoles.

KW - 2-aminoimidazoles

KW - ring closure

KW - silver

KW - spiro compounds

KW - tandem reaction

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ER -

Diversity-oriented silver(i)-mediated synthesis of spiro-2-aminoimidazoles

Abstract

Keywords

ASJC Scopus subject areas

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