Under appropriate reaction conditions 10-ethylphenothiazine 1 undergoe
s lithiation at C-4 using an excess of sec-butyllithium-N,N,N',N'-tetr
amethyl in diethyl ether, Reaction of the lithiated intermediate with
a variety of carbon, halogen, sulfur and silicon electrophiles affords
several new 4-substituted 10-ethylphenothiazines 3a-i in good yields.