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Base‐Promoted Synthesis of Polysubstituted 4‐Aminoquinolines from Ynones and 2‐Aminobenzonitriles under Transition‐Metal‐Free Conditions
Author(s) -
Kumar Ankit,
Mishra Pawan K.,
Saini Kapil Mohan,
Verma Akhilesh K.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202100023
Subject(s) - chemistry , intramolecular force , annulation , combinatorial chemistry , substrate (aquarium) , atom economy , transition metal , base (topology) , scope (computer science) , organic chemistry , stereochemistry , catalysis , computer science , mathematical analysis , oceanography , mathematics , geology , programming language
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 S N Ar mechanism.