Superacidic Cyclization of Activated Anthranilonitriles into 2‑Unsubstituted-4-aminoquinolines

4-Aminoquinolines were prepared in a three-step synthesis starting from substituted anthranilonitriles. The condensation on 1,1,1-trichloro-4-ethoxybut-3-enone proceeded efficiently either neat or in refluxing EtOH. Cyclization in superacidic trifluoromethanesulfonic acid provided unstable intermedi...

Full description

Saved in:
Bibliographic Details
Published in:Organic letters 2017-08, Vol.19 (16), p.4203-4206
Main Authors: Lavrard, Hubert, Larini, Paolo, Popowycz, Florence
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:4-Aminoquinolines were prepared in a three-step synthesis starting from substituted anthranilonitriles. The condensation on 1,1,1-trichloro-4-ethoxybut-3-enone proceeded efficiently either neat or in refluxing EtOH. Cyclization in superacidic trifluoromethanesulfonic acid provided unstable intermediate, which upon treatment with NaOEt in ethanol, afforded the expected esters. Theoretical investigations pointed out a monoprotonated nitrilium as the reactive species during the cyclization process.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b01798