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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Bibliographic Details
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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Summary: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.
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.7b02844