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Incorporation of azo group at axial position of silatranes: synthesis, characterization and antimicrobial activity
Author(s) -
Singh Gurjaspreet,
Saroa Amandeep,
Girdhar Shally,
Rani Sunita,
ChoquesilloLazarte Duane,
Sahoo Subash Chandra
Publication year - 2015
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.3330
Subject(s) - chemistry , pyrrolidine , thermogravimetric analysis , urea , silane , triethanolamine , azobenzene , medicinal chemistry , polymer chemistry , ketene , organic chemistry , molecule , analytical chemistry (journal)
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.