Amide derivatives of 3-aminopropylsilatrane

Silatranes bearing an amide group in the axial chain have been synthesized by the reaction of 1-(3-aminopropyl)silatrane with arylchalcogenylacetic acids (Het)ArYCH₂CO₂H [(Het)Ar=2-MeC₆H₄, 4-Cl-2-MeC₆H₃, 4-ClC₆H₄, 3-indolyl; Y=O, S], and their structures have been established by ¹H,¹³C, ¹⁵N, ²⁹Si NMR and IR spectroscopy. When 4-chlorophenylsulfonylacetic acid was employed, the reaction proceeded unexpectedly via the 4-chlorophenyl methyl sulfone intermediate and resulted in methyl 4-[3-(1 silatranyl)propylamino]phenyl sulfone.