Jump to main content
Jump to site search

Issue 44, 2018
Previous Article Next Article

Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines

Author affiliations

Abstract

The synthesis of 2,4-disubstituted quinazolines by a palladium-catalyzed reaction of arylboronic acids with N-(2-cyanoaryl)benzamides has been developed with moderate to excellent yields. The method shows good functional group tolerance. In particular, halogen and hydroxyl substituents, which are amenable for further synthetic elaborations, are well tolerated. Moreover, the present synthetic route could be readily scaled up to gram quantity without difficulty. The mechanism possibly involves nucleophilic addition to the nitrile function, forming an imine intermediate followed by an intramolecular addition to the amide and dehydration to the quinazoline ring.

Graphical abstract: Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines

Back to tab navigation

Supplementary files

Publication details

The article was received on 28 Sep 2018, accepted on 24 Oct 2018 and first published on 25 Oct 2018


Article type: Paper
DOI: 10.1039/C8OB02421A
Citation: Org. Biomol. Chem., 2018,16, 8596-8603
  •   Request permissions

    Pd-Catalyzed tandem reaction of N-(2-cyanoaryl)benzamides with arylboronic acids: synthesis of quinazolines

    J. Zhu, Y. Shao, K. Hu, L. Qi, T. Cheng and J. Chen, Org. Biomol. Chem., 2018, 16, 8596
    DOI: 10.1039/C8OB02421A

Search articles by author

Spotlight

Advertisements