Abstract
The reactivity of squarylferrocenes was studied in the addition of several N-centered nucleophiles. A total of seven simple amines (primary and secondary) were added to both monosquarylferrocene and 1,1′-bissquarylferrocene to generate 14 ferrocenylsquaramides in 8598%. Likewise, five aminoesters were added to the same scaffolds to produce a novel family of 10 ferrocene-aminoester conjugates in good to excellent yields (57-95%).
Highlights
After over fifty years of its discovery, ferrocene has become the starting material for the preparation of compounds with applications in different fields.[1]
A large number of reports have appeared in the literature dealing with the synthesis and biological activity of ferrocene bioconjugates.[4]
Some of them have displayed interesting properties such as antiproliferative and anti-bacterial activity.[6]. Within this type of compounds, a great deal of efforts has focused on the synthesis and study of the properties of ferrocenepeptides
Summary
After over fifty years of its discovery, ferrocene has become the starting material for the preparation of compounds with applications in different fields.[1]. We report the initial study of the reactivity of these scaffolds with simple amines and aminoesters which can help pave the way for the preparation of more elaborate organometallic peptides. Due to the fact that an excess of the amines were used in all cases, no evidence of the double addition product was observed in the case of piperazine in the 1H NMR spectrum of the crude material (entries 3 and 10).
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