Regioselective Synthesis of V-Shaped Bistriazinyl-phenanthrolines

详细信息    查看全文

• 作者：Niall T. Coogan ; Michael A. Chimes ; James Raftery ; Pavle Mocilac ; Melissa A. Denecke
• 刊名：Journal of Organic Chemistry
• 出版年：2015
• 出版时间：September 4, 2015
• 年：2015
• 卷：80
• 期：17
• 页码：8684-8693
• 全文大小：586K
• ISSN：1520-6904

文摘

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鈥?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鈥揌路路路O hydrogen bonding in the Z isomer explaining its lower solubility in water.