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1 2005

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Preparation of New Phenol-based Acyclic Ligands with Double Set of Coordination Sites

Ghaffarinia A., Golchoubian H.

Polish Journal of Chemistry

2005

Vol. 79 / nr 1

83-87

Aconvenient four-step preparation of the two compartmental ligands 1,6-bis(2-pyridyl)- 2,5-bis(2-hydroxy-3-hydroxymethyl-5-chlorobenzyl)-2,5-diazahexane 3a and 1,7-bis (2-pyridyl)-2,6-bis(2-hydroxy-3-hydroxymethyl-5-chlorobenzyl)-2,6-diazaheptane 3b starting from 4-chlorophenol 4 is reported. Compound 4 was converted to triol 5 which was then protected to 2,2-dimethyl-6-chloro-8-(hydroxymethyl)benzo-1,3-dioxin 6with 2-methoxy propene. Compound 6 was chlorinated to 2,2-dimethyl-6-chloro-8-(chloromethyl) benzo-1,3-dioxin 7 and then reacted with 1,6-bis(2-pyridyl)-2,5-diazahexane or 1,7-bis(2-pyridyl)-2,6-diazaheptane in the presence of Na2CO3 in dioxane. Subsequent acid hydrolysis gave 3a and 3b, respectively. The total yields were 38%.