Organic & Biomolecular Chemistry 2003-05-07

DOTTADs--readily made novel metal ligands with multivariant functionality.

Andrea Arany, Otto Meth-Cohn, Miklós Nyerges

Index: Org. Biomol. Chem. 1(9) , 1545-51, (2003)

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Abstract

The interaction of Hantzsch pyridinecarboxylic acids with dialkylformamides and POCl3, followed by treatment with NH4OH yields 1,8-dioxo-1,2,7,8-tetrahydro-2,7,10-triazaanthracenes (DOTTADs), which have great potential as useful ligands for Group I and II metals and some transition metals. The corresponding Hantszch esters similarly for DOTTADs or their bis-imines by way of isolable intermediates, which are then treated with an amine RNH2. DOTTAD-imines are also available from DOTTADs with amines and this reaction is also effective with 1,8-diamino-3,6-dioxaoctane to give macrocyclic analogues, as well as with chiral amines. DOTTAD-imines can be reduced with diethylsilane and Wilkinson's catalyst to the corresponding amines, which can also be formed from DOTTADs by reductive amination with amines and Na(AcO)3BH. Mono-aldols of DOTTADs are easily formed by treatment of DOTTADs with acetone.