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 [1] [2]. 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 [3]. In the third step this compound is oxidized by Red lead to carbazole itself. Another classic is the Bucherer carbazole synthesis.
Related aromatic compounds
References
- ↑ Borsche, Ann., 359, 49 (1908)
- ↑ Drechsel, J. prakt. Chem., [2] 38, 69 (1888)
- ↑ Organic Syntheses, Coll. Vol. 4, p.884 (1963); Vol. 30, p.90 (1950). Link