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Faggyas RJ, Grace M, Williams L, et al. Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones. J Org Chem. 2018;83(20):12595-12608doi: 10.1021/acs.joc.8b01910.
Faggyas, R. J., Grace, M., Williams, L., & Sutherland, A. (2018). Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones. The Journal of organic chemistry, 83(20), 12595-12608. https://doi.org/10.1021/acs.joc.8b01910
Faggyas, Réka J, et al. "Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones." The Journal of organic chemistry vol. 83,20 (2018): 12595-12608. doi: https://doi.org/10.1021/acs.joc.8b01910
Faggyas RJ, Grace M, Williams L, Sutherland A. Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones. J Org Chem. 2018 Oct 19;83(20):12595-12608. doi: 10.1021/acs.joc.8b01910. Epub 2018 Oct 02. PMID: 30230840.
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J Org Chem. 2018 Oct 19;83(20):12595-12608. doi: 10.1021/acs.joc.8b01910. Epub 2018 Oct 02.

Multibond Forming Tandem Reactions of Anilines via Stable Aryl Diazonium Salts: One-Pot Synthesis of 3,4-Dihydroquinolin-2-ones.

The Journal of organic chemistry

Réka J Faggyas, Megan Grace, Lewis Williams, Andrew Sutherland

Affiliations

  1. WestCHEM, School of Chemistry, The Joseph Black Building , University of Glasgow , Glasgow G12 8QQ , United Kingdom.

PMID: 30230840 DOI: 10.1021/acs.joc.8b01910

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.

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