O- and S-containing 1-azadiene derivatives of 3-aminopropylsilatrane

Abstract

Silatranes bearing the aryl(hetaryl)-substituted 1-azadienyl moiety ((Het)ArCH=C(YR) C(H)=N- (Y = O, S)) were synthesized by the reaction of 1-(3-aminopropyl)silatrane with 2-alkoxy- and 2-alkylthio-3-(het)arylpropenals. The structures and stereoisomeric compositions of the synthesized compounds were proved by elemental analysis, IR spectroscopy, 1D 1H, 13C, 15N, 29Si, and 2D NMR experiments, mass spectrometry, and DFT calculations. O-Containing compounds exist exclusively as the 1E,2Z isomers, while S-containing derivatives are the mixtures of the 1E,2Z and 1E,2E stereoisomers. Newly synthesized chalcogen-containing poly-functional compounds represent the promising building blocks for design and synthesis of advanced materials and pharmaceuticals.