Abstract: A number of partly reduced N-heterocycles, 2-15, have been prepared by reductive silylation of aromatic precursors. The N-silyl substituents stabilize unusual electronic structures such as the 1, 4-dihydropyrazine system toward rearrangements. In addition, R3Si substitution is likely to cause planarization at the amino nitrogen atoms. This may lead to cyclic 8-*-electron conjugation, as has been established, eg, for 1, 4-bis (trimethyIsily1)-1, ...