Regioselectivity of Friedländer Quinoline Syntheses

Optically active, bicyclic ketones were submitted to Friedländer quinoline syntheses with 2‐aminobenzaldehyde to yield regioisomeric linear or angular products. When starting from trans‐configured ketones, the linear products are the major isomers (ratios ranging from 76:24 to >98/2). With cis‐co...

Full description

Saved in:
Bibliographic Details
Published in:European Journal of Organic Chemistry 2008-04, Vol.2008 (10), p.1811-1816
Main Authors: Diedrich, Claas Lüder, Haase, Detlev, Saak, Wolfgang, Christoffers, Jens
Format: Article
Language:English
Subjects:
Annulation
Friedländer synthesis
Heterocycles
Quinoline derivatives
Regioselectivity
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:Optically active, bicyclic ketones were submitted to Friedländer quinoline syntheses with 2‐aminobenzaldehyde to yield regioisomeric linear or angular products. When starting from trans‐configured ketones, the linear products are the major isomers (ratios ranging from 76:24 to >98/2). With cis‐configured ketones the angular products are predominantly formed, although with lower regioselectivity.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008) Depending on the relative configuration of starting bicyclic ketones (cis or trans),either linear or angular quinoline annulation can take place with high selectivity.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.200701179