Regioselective synthesis of V-shaped bistriazinyl-phenanthrolines

Niall T Coogan, Michael A Chimes, James Raftery, Pavle Mocilac, Melissa A Denecke

Research output: Contribution to journalArticlepeer-review


A new, regioselective synthesis of V-shaped 2,9-bis(6-(4-halophenyl)-1,2,4-triazin-3-yl)-1,10-phenanthrolines (4XPhBTPhen) ligands was developed, creating access to a simple and reliable synthesis of precursors for future supramolecular actinide complexing systems. Described is a reactant-directed regioselective synthetic method, which was found to be high yielding and reliable and yields exclusively 6,6′-phenyl BTPhen derivatives (including 4-chloro and 4-bromo) in five simple steps. Molecular and crystal structures of PhBTP and PhBTPhen products are fully determined and both were found to be in space group C2/c. Additionally, molecular and crystal structures of Z and E isomers of 2-hydrazono-2-phenylacetaldehyde oxime, a reagent in the synthetic route, reveal existence of strong intramolecular N–H···O hydrogen bonding in the Z isomer explaining its lower solubility in water.
Original languageEnglish
Pages (from-to)8684-8693
Number of pages9
JournalThe Journal of organic chemistry
Issue number17
Publication statusPublished - 13 Aug 2015

Research Beacons, Institutes and Platforms

  • Dalton Nuclear Institute


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