title: DOTTADs--readily made novel metal ligands with multivariant functionality.
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.
authors.affiliation: Institute of Pharmacy, Chemistry and Biomedical Sciences, Sunderland University, Sunderland, UK SR1 3SD.
authors.forename: Andrea
authors.initials: A
authors.lastname: Arany
authors.forename: Otto
authors.initials: O
authors.lastname: Meth-Cohn
authors.forename: Miklós
authors.initials: M
authors.lastname: Nyerges