6-CHLORO-1 2 3 4-TETRAHYDROCARBAZOLE9&

General procedure: Cyclohexanone (0.91 g, 10.0 mmol) was mixed with [(HSO3- p)2im][CF3SO3] (0.5 mmol) in water (15 mL), and phenylhydrazine hydrochloride (1.44 g, 10.0 mmol) was added. The mixture was then stirred at 100 8C for about 15 min under microwave irradiation. Reaction progress was monitored by GC–MS. After completion, the reaction mixture was cooled to room temperature, and 1, 2, 3, 4-tetrahydrocarbazole was obtained by filtration. The remaining mixture of [(HSO3-p)2im][CF3SO3]/H2O was reused directly.General procedure: A substituted phenyl hydrazine. HCl (4.61 mmol) was added to the mixture of cyclohexanone (4.61 mmol) and acetic acid (15 ml) portion wise for 30 min. The mixture was then refluxed for 8 h and progress of reaction was monitored by thin layer chromatography. The reaction mixture was cooled and poured into crushed ice. The solid product was separated, filtered, dried and recrystallized from the methanol solvent.Sulfonic acid ionic liquid 1b (0.125 mmol), p-chlorophenylhydrazine hydrochloride (25 mmol), Cyclohexanone (25 mmol) water 15 mL sequentially added to the reaction vessel, Placed in a reactor, under mechanical stirring at 100 ° C for 15 minutes, After cooling to room temperature, the mixture was filtered and dried to give 5.01 g, yield 87percent.General procedure: The amalgamation of tetrahydrocarbazoles were based on Fischer-indole synthesis method. In general it was carried out by dissolving 8.8 g (0.08 mol) of cyclohexanone in 50 ml of glacial acetic acid, to this 8.8 g (0.08 mol) of substituted phenyl hydrazine was added and boiled under reflux for 15 min. the solution was cooled, crystals formed were isolated by filtration. Crude product was further purified by recrystallization from aqueous ethanol. A total of four derivatives were synthesized by this route and were subjected to characterization.B. General procedure: Cyclohexanone (0.91 g, 10.0 mmol) was mixed with [(HSO3- p)2im][CF3SO3] (0.5 mmol) in water (15 mL), and phenylhydrazine hydrochloride (1.44 g, 10.0 mmol) was added. The mixture was then stirred at 100 8C for about 15 min under microwave irradiation. Reaction progress was monitored by GC-MS. After completion, the reaction mixture was cooled to room temperature, and 1, 2, 3, 4-tetrahydrocarbazole was obtained by filtration. The remaining mixture of [(HSO3-p)2im][CF3SO3]/H2O was reused directly.General procedure: A substituted phenyl hydrazine. HCl (4.61 mmol) was added to the mixture of cyclohexanone (4.61 mmol) and acetic acid (15 ml) portion wise for 30 min. The mixture was then refluxed for 8 h and progress of reaction was monitored by thin layer chromatography. The reaction mixture was cooled and poured into crushed ice. The solid product was separated, filtered, dried and recrystallized from the methanol solvent.Sulfonic acid ionic liquid 1b (0.125 mmol), p-chlorophenylhydrazine hydrochloride (25 mmol), Cyclohexanone (25 mmol) water 15 mL sequentially added to the reaction vessel, Placed in a reactor, under mechanical stirring at 100 C for 15 minutes, After cooling to room temperature, the mixture was filtered and dried to give 5.01 g, yield 87%.

Molecular Weight:205.68
XLogP3:3.9
Hydrogen Bond Donor Count:1
Exact Mass:205.0658271
Monoisotopic Mass:205.0658271
Topological Polar Surface Area:15.8
Heavy Atom Count:14
Complexity:218
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes