Issue 2, 2011
From the journal:

Organic & Biomolecular Chemistry

Synthesis of substituted 8-aminoquinolines and phenanthrolines through a Povarov approach†‡

Kavita De,§a   Julien Legros,*a   Benoit Crousse,a   Srinivasan Chandrasekaranb  and  Danièle Bonnet-Delpona  

* Corresponding authors

a Laboratoire BioCIS-CNRS, Faculté de Pharmacie, Univ Paris Sud, 5 rue J.B. Clément, France
E-mail: julien.legros@u-psud.fr
Fax: +33 1 46 83 57 40
Tel: +33 1 46 83 57 44

b Department of Organic Chemistry, Indian Institute of Science, Bangalore 560012, Karnataka, India

Abstract

The synthesis of 8-aminoquinolines and 1,10-phenanthrolines with substituents in α of the nitrogen has been performed through an inverse-demanding aza-Diels–Alder (Povarov reaction) in the fluoroalcohols TFE or HFIP. This path involves simple starting materials: 1,2-phenylenediamines, enol ethers and aldehydes.

Graphical abstract: Synthesis of substituted 8-aminoquinolines and phenanthrolines through a Povarov approach

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Article information

DOI
https://doi.org/10.1039/C0OB00496K
Article type
Communication
Submitted
27 Jul 2010
Accepted
23 Sep 2010
First published
18 Oct 2010

Org. Biomol. Chem., 2011,9, 347-350

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Synthesis of substituted 8-aminoquinolines and phenanthrolines through a Povarov approach

K. De, J. Legros, B. Crousse, S. Chandrasekaran and D. Bonnet-Delpon, Org. Biomol. Chem., 2011, 9, 347 DOI: 10.1039/C0OB00496K

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