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

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 sta...

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Published in:Journal of organic chemistry 2018-01, Vol.83 (2), p.854-861
Main Authors: Collet, Jurriën W, Ackermans, Kelly, Lambregts, Jeffrey, Maes, Bert U.W, Orru, Romano V.A, Ruijter, Eelco
Format: Article
Language:English
Subjects:
aromatic hydrocarbons
chemical structure
chloroquine
cyclization reactions
organic chemistry
synthesis
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cited_by cdi_FETCH-LOGICAL-a528t-4eee8bf24b50e906e1e1ea729ef7a9f6606428fa9e3bf0fac20fb2b86537348c3
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container_title Journal of organic chemistry
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creator Collet, Jurriën W
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description 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.
doi_str_mv 10.1021/acs.joc.7b02844
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source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
subjects aromatic hydrocarbons
chemical structure
chloroquine
cyclization reactions
organic chemistry
synthesis
title Modular Three-Component Synthesis of 4‑Aminoquinolines via an Imidoylative Sonogashira/Cyclization Cascade
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