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

Research output: Contribution to JournalArticleAcademicpeer-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.

LanguageEnglish
Pages854-861
Number of pages8
JournalJournal of Organic Chemistry
Volume83
Issue number2
DOIs
Publication statusPublished - 19 Jan 2018

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Cyclization
Cyanides
Chloroquine
Acids
4-aminoquinoline

Cite this

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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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Modular Three-Component Synthesis of 4-Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade. / Collet, Jurriën W.; Ackermans, Kelly; Lambregts, Jeffrey; Maes, Bert U.W.; Orru, Romano V.A.; Ruijter, Eelco.

In: Journal of Organic Chemistry, Vol. 83, No. 2, 19.01.2018, p. 854-861.

Research output: Contribution to JournalArticleAcademicpeer-review

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AU - Ruijter, Eelco

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