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)

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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, Dr 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

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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
746561EPSRC-IAA: Towards a mechanistic understanding of the methanol-to-gasoline reaction over zeolitesDavid LennonEngineering and Physical Sciences Research Council (EPSRC)EP/K503903/1CHEM - CHEMISTRY