Synthesis of Quinazolin-4-ones by Copper-Catalyzed Isocyanide Insertion

Jurriën W. Collet; Edith A. Van Der Nol; Tom R. Roose; Bert U.W. Maes; Eelco Ruijter; Romano V.A. Orru

doi:10.1021/acs.joc.0c00771

Synthesis of Quinazolin-4-ones by Copper-Catalyzed Isocyanide Insertion

Jurriën W. Collet, Edith A. Van Der Nol, Tom R. Roose, Bert U.W. Maes, Eelco Ruijter, Romano V.A. Orru^*

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

Herein, we report a novel copper-catalyzed imidoylative cross-coupling/cyclocondensation reaction between 2-isocyanobenzoates and amines efficiently producing quinazolin-4-ones. The reaction utilizes Cu(II) acetate as an environmentally benign catalyst in combination with a mild base and proceeds well in anisole, a recommended, sustainable solvent. Additionally, the reaction does not require dry conditions or inert atmospheres for optimal performance. The scope of this isocyanide insertion reaction is rather broad, tolerating various functionalized isocyanobenzoates and a range of substituted amines, although the use of aromatic amines as nucleophiles requires microwave heating.

Original language	English
Pages (from-to)	7378-7385
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	85
Issue number	11
Early online date	13 May 2020
DOIs	https://doi.org/10.1021/acs.joc.0c00771
Publication status	Published - 5 Jun 2020

Funding

Financial support from The Netherlands Organization for Scientific Research (NWO), the Research Foundation Flanders (FWO), the Francqui Foundation, and the University of Antwerp (BOF Scholarship to J.W.C.) is gratefully acknowledged.

Funders	Funder number
Francqui Foundation
Netherlands Organization for Scientific Research
Fonds Wetenschappelijk Onderzoek
Nederlandse Organisatie voor Wetenschappelijk Onderzoek
Bijzonder Onderzoeksfonds UGent
Universiteit Antwerpen
Fondation Francqui - Stichting

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "Synthesis of Quinazolin-4-ones by Copper-Catalyzed Isocyanide Insertion",

abstract = "Herein, we report a novel copper-catalyzed imidoylative cross-coupling/cyclocondensation reaction between 2-isocyanobenzoates and amines efficiently producing quinazolin-4-ones. The reaction utilizes Cu(II) acetate as an environmentally benign catalyst in combination with a mild base and proceeds well in anisole, a recommended, sustainable solvent. Additionally, the reaction does not require dry conditions or inert atmospheres for optimal performance. The scope of this isocyanide insertion reaction is rather broad, tolerating various functionalized isocyanobenzoates and a range of substituted amines, although the use of aromatic amines as nucleophiles requires microwave heating.",

author = "Collet, {Jurri{\"e}n W.} and {Van Der Nol}, {Edith A.} and Roose, {Tom R.} and Maes, {Bert U.W.} and Eelco Ruijter and Orru, {Romano V.A.}",

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AU - Collet, Jurriën W.

AU - Van Der Nol, Edith A.

AU - Roose, Tom R.

AU - Maes, Bert U.W.

AU - Ruijter, Eelco

AU - Orru, Romano V.A.

PY - 2020/6/5

Y1 - 2020/6/5

N2 - Herein, we report a novel copper-catalyzed imidoylative cross-coupling/cyclocondensation reaction between 2-isocyanobenzoates and amines efficiently producing quinazolin-4-ones. The reaction utilizes Cu(II) acetate as an environmentally benign catalyst in combination with a mild base and proceeds well in anisole, a recommended, sustainable solvent. Additionally, the reaction does not require dry conditions or inert atmospheres for optimal performance. The scope of this isocyanide insertion reaction is rather broad, tolerating various functionalized isocyanobenzoates and a range of substituted amines, although the use of aromatic amines as nucleophiles requires microwave heating.

AB - Herein, we report a novel copper-catalyzed imidoylative cross-coupling/cyclocondensation reaction between 2-isocyanobenzoates and amines efficiently producing quinazolin-4-ones. The reaction utilizes Cu(II) acetate as an environmentally benign catalyst in combination with a mild base and proceeds well in anisole, a recommended, sustainable solvent. Additionally, the reaction does not require dry conditions or inert atmospheres for optimal performance. The scope of this isocyanide insertion reaction is rather broad, tolerating various functionalized isocyanobenzoates and a range of substituted amines, although the use of aromatic amines as nucleophiles requires microwave heating.

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Synthesis of Quinazolin-4-ones by Copper-Catalyzed Isocyanide Insertion

Abstract

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