Synthesis and Preliminary Antibacterial Activities of novel Schiff bases Derivatives of 3,6-diazahomoadamantane

Chemistry Department, College of Science, University of Kerbala, Kerbala, Iraq

Abstract

This work includes synthesis of new Schiff bases derivatives of diazahomoadamntane.

First, 1,3,6,8-tetraazatricyclo[4.4.1.13,8]dodecane 1 was treated with anisyl acetone   to produce

1-(4-methoxybenzyl)-3,6-diazahomoadamantan-9-one

1. 2. Reaction of ketone compound 2 with aqueous hydrazine yielded 1-(4-methoxybenzyl)-3,6-diazahomoadamantan-9-hydrazone
2. 3. Condensation of hydrazone derivative 3 with some benzaldehydes including (4-carboxybenzaldehyde, 3-chlorobenzaldehyde, 3-hydroxybenzaldehyde, 4-nitrobenzaldehyde) under reflux in ethanol afforded imine derivatives of diazahomoadamntane

4a­­–d. The structures of newly synthesized derivatives have been deduced via FT-IR, ¹H NMR, and Mass spectral means. Antibacterial test of new derivatives 4a-d showed that compounds 4b, 4c, and 4d have activity against Staphylococcus aurous more than Gentamycin as a reference drug, also compound 4d pointed higher activity against Escherichia coli than the standard drug.