Synthesis of 2-arylamino-3-cyanoquinolines: Via a cascade reaction through a nitrilium intermediate
Journal
Organic and Biomolecular Chemistry
Journal Volume
18
Journal Issue
5
Pages
975-982
Date Issued
2020
Author(s)
Abstract
A new method for the preparation of 2-amino-3-cyanoquinolines from readily available aryldiazonium salts, 2-aminoarylketones, and malononitrile via a cascade reaction is reported. This one-pot approach involves the in situ generation of an N-arylnitrilium intermediate from the direct reaction of aryldiazonium salts and malononitrile, which undergoes intermolecular amination, Knoevenagel condensation, and then aromatization to yield the desired compound in moderate to good yields. This methodology features a quick assembly of C2 and C3 functionalized quinolines.
Type
journal article