Carbazole

Carbazole is an aromatic heterocyclic organic compound. It has a tricyclic structure, consisting of two six-membered benzene ring fused on either side of a five-membered nitrogen-containing ring. The compound's structure is based on the indole structure but in which a second benzene ring is fused onto the five-membered ring at the 2-3 position of indole (equivalent to the 4a-9a double bond in carbazole).

A classic laboratory organic synthesis for carbazole is the Borsche-Drechsel cyclization. In the first step phenylhydrazine is condensed with cyclohexanone to the corresponding imine. The second step is a hydrochloric acid catalyzed rearrangement reaction and ring-closing reaction to tetrahydrocarbazole. In one modification both steps are rolled into one by carrying out the reaction in acetic acid. In the third step this compound is oxidized by Red lead to carbazole itself. Another classic is the Bucherer carbazole synthesis.

Related aromatic compounds

 * Indoline
 * Indole
 * Carboline
 * Pyrrole