Synthesis
In a 100 mL three-necked flask, phenylhydrazine hydrochloride (1.44 g, 10 mmol) was added in portions over 30 minutes to a 30 mL solution of cyclohexanone (1.00 g, 10 mmol) in acetic acid. The mixture was then refluxed for 8 hours until the reaction was complete. The reaction was cooled to room temperature and then poured into ice water. The solid was collected by filtration and recrystallized from methanol to give intermediate 1,2,3,4-tetrahydrocarbazole as a white solid, 1.44 g, yield 85%.
Chemical Properties
beige crystalline powder
Uses
1,2,3,4-Tetrahydrocarbazole can be used as a starting material to prepare:
- Spiro[cyclopentane-1,2′-indolin-3′-one] by photooxygenation.
- 9-Acyl-1,2,3,4-tetrahydrocarbazoles by N-acylation reactions.
- Carbazole via palladium-catalyzed asymmetric hydrogenation reaction.
Uses
It finds its application as a pharmaceutical intermediate and in the synthesis of aspidospermidine alkaloids.
