Multibond forming tandem reactions of anilines via stable aryl diazonium salts: one-pot synthesis of 3,4-dihydroquinolin-2-ones

Faggyas, R. J., Grace, M., Williams, L. and Sutherland, A. (2018) Multibond forming tandem reactions of anilines via stable aryl diazonium salts: one-pot synthesis of 3,4-dihydroquinolin-2-ones. Journal of Organic Chemistry, 83(20), pp. 12595-12608. (doi: 10.1021/acs.joc.8b01910) (PMID:30230840)

Abstract

A fast and effective one-pot tandem process that generates Heck coupled products from readily available anilines via stable aryl diazonium tosylate salts was developed. The mild and simple procedure involves rapid formation of aryl diazonium salts using a polymer-supported nitrite reagent and p-tosic acid, followed by a base-free Heck–Matsuda coupling with acrylates and styrenes. Using 2-nitroanilines as substrates, the one-pot tandem process was extended for the direct synthesis of 3,4-dihydroquinolin-2-ones. In this case, following diazotization and Heck–Matsuda coupling to give methyl cinnamates, addition of hydrogen and reutilization of the palladium catalyst for reduction of the nitro group and hydrogenation of the alkene resulted in efficient formation of 3,4-dihydroquinolin-2-ones. The synthetic utility of this one-pot, four-stage process was demonstrated with the five-pot synthesis of a quinolinone-based sodium ion channel modulator.

• Item Type: Articles
• Status: Published
• Refereed: Yes
• Glasgow Author(s) Enlighten ID: Sutherland, Professor Andrew and Faggyas, Réka and Williams, Mr Lewis
• Authors: Faggyas, R. J., Grace, M., Williams, L., and Sutherland, A.
• College/School: College of Science and Engineering > School of Chemistry
• Journal Name: Journal of Organic Chemistry
• Publisher: American Chemical Society
• ISSN: 0022-3263
• ISSN (Online): 1520-6904
• Published Online: 19 September 2018
• Copyright Holders: Copyright © 2018 American Chemical Society
• First Published: First published in Journal of Organic Chemistry 83(20): 12595-12608
• Publisher Policy: Reproduced under a Creative Commons License

Project Code	Award No	Project Name	Principal Investigator	Funder's Name	Funder Ref	Lead Dept
74656	1	EPSRC-IAA: Towards a mechanistic understanding of the methanol-to-gasoline reaction over zeolites	David Lennon	Engineering and Physical Sciences Research Council (EPSRC)	EP/K503903/1	CHEM - CHEMISTRY