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Issue 40, 2019
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Tuning the reaction pathways of phenanthroline-Schiff bases: routes to novel phenanthroline ligands

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Abstract

Pyrido-phenanthrolin-7-one compounds are structural analogues of the cytotoxic alkaloid, ascididemin, and would be expected to have interesting biological activities. Synthetic strategies are reported for a novel simple route to form this class of ligand. 1,10-Phenanthrolin-5,6-dione reacts with L-phenylalanine alkyl esters and their para-substituted analogues to form both a phenanthroline–oxazine and a pyrido-phenanthrolin-7-one product. The nature of the major product is dependent on the electronic properties of the para substituent. Successful metal coordination to the pyrido-phenanthrolin-7-one ligand is also presented.

Graphical abstract: Tuning the reaction pathways of phenanthroline-Schiff bases: routes to novel phenanthroline ligands

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Article information


Submitted
28 Jul 2019
Accepted
23 Sep 2019
First published
03 Oct 2019

Dalton Trans., 2019,48, 15283-15289
Article type
Paper

Tuning the reaction pathways of phenanthroline-Schiff bases: routes to novel phenanthroline ligands

M. Ahmed, D. Rooney, M. McCann, J. Casey, K. O'Shea and B. Twamley, Dalton Trans., 2019, 48, 15283
DOI: 10.1039/C9DT03084K

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