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

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

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

Author(s) -

Jurriën W. Collet,

Kelly Ackermans,

Jeffrey Lambregts,

Bert U. W. Maes,

Romano V. A. Orrù,

Eelco Ruijter

Publication year - 2017

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.7b02844

Subject(s) - aminoquinolines , sonogashira coupling , chemistry , combinatorial chemistry , component (thermodynamics) , organic chemistry , palladium , catalysis , physics , thermodynamics

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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