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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.

SUBMITTER: Collet JW

PROVIDER: S-EPMC7281788 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature

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

Collet Jurriën W JW van der Nol Edith A EA Roose Tom R TR Maes Bert U W BUW Ruijter Eelco E Orru Romano V A RVA

The Journal of organic chemistry 20200526 11

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 react ...[more]

PMID: 32400159

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