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Superbase‐Mediated Indirect Friedländer Reaction: A Transition Metal‐Free Oxidative Annulation toward Functionalized Quinolines
Author(s) -
P. Rahul,
P. R. Nitha,
Omanakuttan Vishnu K.,
Babu Sheba Ann,
Sasikumar P.,
Praveen Vakayil K.,
Hopf Henning,
John Jubi
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202000365
Subject(s) - chemistry , annulation , superbase , condensation reaction , moiety , chalcone , alcohol , combinatorial chemistry , transition metal , organic chemistry , medicinal chemistry , photochemistry , catalysis
A superbase mediated indirect Friedländer 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.

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