McMurry (Kap 18,9) - fused ring heterocycles

Question 1

In page 670 you can see the different fused ring heterocycles/polycyclic compounds.

What is the chemistry of those?

Answer 1

Quinoline and isoquinoline are both:

1) basic

2) undergo electrophillic substitutions

less easily then benzene though.

see page 670 for example.

Indole (has a nonbasic nitrogen, undergo electrophillic substitution more easily then benzene).

Purine (has three basic nitrogens - those that are a part of the double bond, the other one that is not part of the double bond is non basic - its electron is distributed as part of the pi-electron system).