Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 20, Pages 3081-3089Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000365
Keywords
Annulation; Nitrogen heterocycles; Quinolines; Superbases; Synthetic methods
Categories
Funding
- CSIR
- UGC
- Alexander von Humboldt Foundation
Ask authors/readers for more resources
A superbase mediated indirect Friedlander reaction towards functionalized quinolines has been realized. The reaction was performed with o-aminobenzyl alcohol and ketones having an active methylene moiety in the presence of KOH and in DMSO. The reaction proceeds predominantly via initial formation of an imine intermediate and subsequent oxidation of the benzyl alcohol functionality and condensation to afford substituted quinolines. We could also demonstrate that a minor fraction of the reaction proceeds via a chalcone intermediate. The transition metal-free oxidative annulation was found to be general affording 2-substituted, 2,3-disubstituted/fused or multi-substituted quinolines. The reaction was extended towards the functionalization of natural products and the applicability of the reaction for gram-scale synthesis of quinolines was also demonstrated.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available