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 JournalArticleAcademicpeer-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 languageEnglish
Pages (from-to)7378-7385
Number of pages8
JournalJournal of Organic Chemistry
Volume85
Issue number11
Early online date13 May 2020
DOIs
Publication statusPublished - 5 Jun 2020

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