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Base‐promoted synthesis of polysubstituted 4‐aminoquinolines from ynones and 2‐aminobenzonitriles under transition‐metal‐free conditions

Kumar, Ankit, Mishra, Pawan K., Saini, Kapil Mohan and Verma, Akhilesh K. 2021. Base‐promoted synthesis of polysubstituted 4‐aminoquinolines from ynones and 2‐aminobenzonitriles under transition‐metal‐free conditions. Advanced Synthesis and Catalysis 363 (10) , pp. 2546-2551. 10.1002/adsc.202100023

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Abstract

A transition‐metal‐free and base‐promoted one‐pot reaction of ynones with 2‐aminobenzonitriles is described. The reaction was initiated through sequential aza‐Michael addition/intramolecular annulation to afford various multisubstituted 4‐aminoquinolines and 4‐amino‐1,8‐naphthyridines in good to excellent yields. Operational simplicity, high atom‐economy with broad substrate scope makes this protocol more attractive. Also, the gram‐scale synthesis and further transformation of the product were studied. Additionally, 2‐haloarylyones as substrate provide N‐arylquinolones as the sole product via the SNAr mechanism.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Wiley
ISSN: 1615-4150
Date of First Compliant Deposit: 24 May 2021
Date of Acceptance: 25 February 2021
Last Modified: 25 Feb 2022 16:28
URI: https://orca.cardiff.ac.uk/id/eprint/141403

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