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J Org Chem ; 80(17): 8684-93, 2015 Sep 04.
Artículo en Inglés | MEDLINE | ID: mdl-26237435

RESUMEN

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.

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