Synthesis of Schiff bases linked to organopropylsilatranes were performed by condensation reaction of post-functionalized silatranes such as aminopropylsilatrane (4), aminopropyl-3,7,10-trimethylsilatrane (5) and N-substituted aminopropylsilatrane (10) with two different aldehydes viz. pyrrole-2-carboxaldehyde and 2-hydroxy- 1-napthaldehyde. The resulting Schiff base substituted silatranes were well characterized by elemental analysis, spectroscopic studies [IR, (H-1, C-13) NMR, and MS]. The structures of two silatranes were confirmed by single crystal X-ray diffraction analysis