Combinatorial synthesis of 4-oxo-4H-imidazo[1,5-a]quinoxalines and 4-oxo-4H-pyrazolo[1,5-a]quinoxalines

Julia H. Spatz; Michael Umkehrer; Cédric Kalinski; Günther Ross; Christoph Burdack; Jürgen Kolb; Thorsten Bach

doi:10.1016/j.tetlet.2007.09.015

Combinatorial synthesis of 4-oxo-4H-imidazo[1,5-a]quinoxalines and 4-oxo-4H-pyrazolo[1,5-a]quinoxalines

Julia H. Spatz
, Michael Umkehrer
, Cédric Kalinski
, Günther Ross
, Christoph Burdack
, Jürgen Kolb
, Thorsten Bach

Chair of Organic Chemistry 1

Priaton GmbH
Technical University of Munich

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

25 Scopus citations

Abstract

A combinatorial synthetic route yielding imidazo[1,5-a]quinoxalines and pyrazolo[1,5-a]quinoxalines is described. The use of 2-fluoroaniline and 1H-imidazole-4-carboxylic acid, respectively, 1H-pyrazole-3-carboxylic acid in the Ugi-reaction (U-4CR) followed by a nucleophilic aromatic substitution (S_NAr) affords the imidazo- as well as the pyrazolo-[1,5-a]quinoxaline moiety in good yield and high diversity.

Original language	English
Pages (from-to)	8060-8064
Number of pages	5
Journal	Tetrahedron Letters
Volume	48
Issue number	45
DOIs	https://doi.org/10.1016/j.tetlet.2007.09.015
State	Published - 5 Nov 2007

Keywords

Imidazo-quinoxaline
Multi-component reaction
Nucleophilic aromatic substitution
Pyrazolo-quinoxaline
Ugi-reaction

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10.1016/j.tetlet.2007.09.015

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title = "Combinatorial synthesis of 4-oxo-4H-imidazo[1,5-a]quinoxalines and 4-oxo-4H-pyrazolo[1,5-a]quinoxalines",

abstract = "A combinatorial synthetic route yielding imidazo[1,5-a]quinoxalines and pyrazolo[1,5-a]quinoxalines is described. The use of 2-fluoroaniline and 1H-imidazole-4-carboxylic acid, respectively, 1H-pyrazole-3-carboxylic acid in the Ugi-reaction (U-4CR) followed by a nucleophilic aromatic substitution (SNAr) affords the imidazo- as well as the pyrazolo-[1,5-a]quinoxaline moiety in good yield and high diversity.",

keywords = "Imidazo-quinoxaline, Multi-component reaction, Nucleophilic aromatic substitution, Pyrazolo-quinoxaline, Ugi-reaction",

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year = "2007",

month = nov,

day = "5",

doi = "10.1016/j.tetlet.2007.09.015",

language = "English",

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T1 - Combinatorial synthesis of 4-oxo-4H-imidazo[1,5-a]quinoxalines and 4-oxo-4H-pyrazolo[1,5-a]quinoxalines

AU - Spatz, Julia H.

AU - Umkehrer, Michael

AU - Kalinski, Cédric

AU - Ross, Günther

AU - Burdack, Christoph

AU - Kolb, Jürgen

AU - Bach, Thorsten

PY - 2007/11/5

Y1 - 2007/11/5

N2 - A combinatorial synthetic route yielding imidazo[1,5-a]quinoxalines and pyrazolo[1,5-a]quinoxalines is described. The use of 2-fluoroaniline and 1H-imidazole-4-carboxylic acid, respectively, 1H-pyrazole-3-carboxylic acid in the Ugi-reaction (U-4CR) followed by a nucleophilic aromatic substitution (SNAr) affords the imidazo- as well as the pyrazolo-[1,5-a]quinoxaline moiety in good yield and high diversity.

AB - A combinatorial synthetic route yielding imidazo[1,5-a]quinoxalines and pyrazolo[1,5-a]quinoxalines is described. The use of 2-fluoroaniline and 1H-imidazole-4-carboxylic acid, respectively, 1H-pyrazole-3-carboxylic acid in the Ugi-reaction (U-4CR) followed by a nucleophilic aromatic substitution (SNAr) affords the imidazo- as well as the pyrazolo-[1,5-a]quinoxaline moiety in good yield and high diversity.

KW - Imidazo-quinoxaline

KW - Multi-component reaction

KW - Nucleophilic aromatic substitution

KW - Pyrazolo-quinoxaline

KW - Ugi-reaction

UR - https://www.scopus.com/pages/publications/35148860238

U2 - 10.1016/j.tetlet.2007.09.015

DO - 10.1016/j.tetlet.2007.09.015

M3 - Article

AN - SCOPUS:35148860238

SN - 0040-4039

VL - 48

SP - 8060

EP - 8064

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 45

ER -

Combinatorial synthesis of 4-oxo-4H-imidazo[1,5-a]quinoxalines and 4-oxo-4H-pyrazolo[1,5-a]quinoxalines

Abstract

Keywords

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