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Abstract
Synthesis of tricyclic derivatives which contain both silicon and nitrogen in the central ring (phenazasilines) as well as a dimethylaminopropyl side chain bonded either to Si or to N are described. Reaction of 4,4′-dibromo-2,2′-dilithio- N-(γ-dimethylaminopropyl)diphenylamine with Me 2SiCl 2 provides a ring brominated silicon analog of the tranquilizer promazine. Reaction of 4,4′-dibromo-2,2′-dilithio- N-methyldiphenylamine with MeSiHCl 2 followed by SiH addition of the phenazasiline to allylamine provided the isomeric derivative. Debromination of three phenazasilines with BuLi followed by hydrolysis demonstrated formation of both 2-bromophenazasilines as well as phenazasilines. Structural comparisons to phenothiazines are discussed.
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