Issue 12, 2003
From the journal:

Organic & Biomolecular Chemistry

DOTTADs – readily made novel metal ligands with multivariant functionality – trans-DOTTADs and semi-DOTTADs

Andrea Arany,a   Otto Meth-Cohn,a   István Berhésb  and  Miklós Nyergesab  

a Institute of Pharmacy, Chemistry and Biomedical Sciences, University of Sunderland, Wharncliffe Street, Sunderland, UK

b Research Group of the Hungarian Academy of Sciences, Department of Organic Chemical Technology, Technical University of Budapest, H-1521 Budapest P.O.B. 91, Hungary

Abstract

Two new ligand systems related to the previously described DOTTADs have been generated in a simple one step reaction. The first, trans-DOTTADs, were formed by Vilsmeier formylation (followed by cyclisation and N-demethylation) of 2,6-dimethyl-3,5-pyrazine-dicarboxylic acid, to give the novel bis-pyridinopyrazine dialdehyde ligands. The corresponding pyrazine diester, reacted similarly to an intermediate iminium ion stage, which gave trans-DOTTAD imines on work-up with amines. The treatment of Hantzsch ester with two equivalents of benzaldehyde gave 7-phenyl-2-(2-phenylethenyl)-7,8-dihydropyrano[4,3-b]pyridin-5-one-3-carboxylic acid. This product underwent similar cyclisation with Vilsmeier reagents to give, for example, 6-methyl-2-(2-phenylethenyl)-8-(phenylhydroxymethyl)-6H-[1,6]naphthyridin-5-one-3-carboxylic acid, an example of a semi-DOTTAD.

Graphical abstract: DOTTADs – readily made novel metal ligands with multivariant functionality – trans-DOTTADs and semi-DOTTADs

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Article information

DOI
https://doi.org/10.1039/B303675H
Article type
Paper
Submitted
04 Apr 2003
Accepted
02 May 2003
First published
19 May 2003

Org. Biomol. Chem., 2003,1, 2164-2167

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DOTTADs – readily made novel metal ligands with multivariant functionality – trans-DOTTADs and semi-DOTTADs

A. Arany, O. Meth-Cohn, I. Berhés and M. Nyerges, Org. Biomol. Chem., 2003, 1, 2164 DOI: 10.1039/B303675H

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