Problems and exercisesFused heterocycles: indole and quinoline
Exercise 1
Why does pyrrole react with electrophiles at C2 but indole at C3? Draw the σ-complex for attack at C3 of indole and explain what would happen to the benzene ring on attack at C2.
Exercise 2
Give the product of quinoline with: a) HNO3/H2SO4 at 0 °C; b) NaNH2 in refluxing toluene; c) basic KMnO4. Justify in each case which ring reacts.