Gurjaspreet Singh, Amandeep Saroa, Shally Girdhar
Aug 1, 2015
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16
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Journal
Applied Organometallic Chemistry
Abstract
4-Aminoazobenzene-derived silatranes bearing urea and aminosuccinimide as linker groups at the axial position are reported. The urea functionality is introduced in a silane (2) by the rearrangement reaction between 3-isocyanatopropyltriethoxysilane and 4-aminoazobenzene. N-(3-silatranylpropyl)-N′-[(p-phenyldiazenyl)phenyl]urea and N-[3-(3,7,10-trimethylsilatranyl)propyl]-N′-[(p-phenyldiazene)phenyl]urea were prepared by transesterification reaction of 2 with triethanolamine and trisisopropanolamine, respectively. An efficient method for CN bond formation is described for the synthesis of 3-(silatranylpropyl)amino-N-[(p-phenyldiazene)phenyl]pyrrolidine-2,5-dione and 3-[(3,7,10-trimethylsilatranyl)propyl]amino-N-[(p-phenyldiazene)phenyl]pyrrolidine-2,5-dione via aza-Michael addition reaction of aminopropylsilatranes with 4-(N-maleimido)azobenzene under mild conditions. All the compounds were well characterized using elemental analysis, spectroscopic techniques, thermogravimetric analysis and X-ray diffraction. UV–visible spectroscopy indicates that the 4-aminoazobenzene-derived silatranes are capable acetate receptors. The synthesized compounds were screened for possible antimicrobial properties with the results showing a modest activity. Copyright © 2015 John Wiley & Sons, Ltd.