Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade

Jurriën W. Collet; Kelly Ackermans; Jeffrey Lambregts; Bert U.W. Maes; Romano V.A. Orru; Eelco Ruijter

doi:10.1021/acs.joc.7b02844

Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade

Jurriën W. Collet, Kelly Ackermans, Jeffrey Lambregts, Bert U.W. Maes, Romano V.A. Orru^*, Eelco Ruijter

^*Corresponding author for this work

Research output: Contribution to Journal › Article › Academic › peer-review

Abstract

We developed a one-pot, two-stage synthetic route to substituted 4-aminoquinolines involving an imidoylative Sonogashira coupling followed by acid-mediated cyclization. This three-component reaction affords pharmaceutically valuable 4-aminoquinolines in a one-pot procedure from readily available starting materials. The reaction tolerates various substituents on the arene as well as the use of secondary and even primary isocyanides. Additionally, the wide tolerance for functionalized isocyanides allows for the one-pot synthesis of various substituted chloroquine analogues as well as other medicinally relevant products.

Original language	English
Pages (from-to)	854-861
Number of pages	8
Journal	Journal of Organic Chemistry
Volume	83
Issue number	2
DOIs	https://doi.org/10.1021/acs.joc.7b02844
Publication status	Published - 19 Jan 2018

Funding

We thank Elwin Janssen for NMR support and maintenance. The research leading to these findings has received financial support from The Netherlands Organization for Scientific Research (NWO).

Funders	Funder number
Netherlands Organization for Scientific Research
Nederlandse Organisatie voor Wetenschappelijk Onderzoek

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abstract = "We developed a one-pot, two-stage synthetic route to substituted 4-aminoquinolines involving an imidoylative Sonogashira coupling followed by acid-mediated cyclization. This three-component reaction affords pharmaceutically valuable 4-aminoquinolines in a one-pot procedure from readily available starting materials. The reaction tolerates various substituents on the arene as well as the use of secondary and even primary isocyanides. Additionally, the wide tolerance for functionalized isocyanides allows for the one-pot synthesis of various substituted chloroquine analogues as well as other medicinally relevant products.",

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AU - Maes, Bert U.W.

AU - Orru, Romano V.A.

AU - Ruijter, Eelco

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Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade

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