17017-64-0

Upstream product

• 19283-50-2 4-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 100-39-0 benzyl bromide 
• 683799-97-5 1-benzyl-2-(pent-4-enyl)-1H-indole 
• 19283-46-6 (Z)-4-methylcyclohexane-1,2-dione 2-phenylhydrazone 
• 589-92-4 1-methylcyclohexan-4-one 
• 683800-26-2 2-(pent-4-en-1-yl)-1H-indole 
• 82185-43-1 N-(trimethylsilyl)-o-toluidine 
• 2396-80-7 methyl 5-hexenoate 
• 62334-20-7 2-hydroxymethylene-4-methylcyclohexanone 

Downstream Products

• 120090-53-1 9-benzyl-1,4-dimethyl-9H-carbazole 
• 87167-62-2 9-benzyl-1,4-dimethyl-9H-carbazole-3-carbaldehyde 
• 129868-46-8 9-benzyl-1,2,3,4-tetrahydro-4-methylcarbazole-1-carbaldehyde 
• 129868-47-9 9-benzyl-1-((N,N-dimethylamino)methyl)-4-methylcarbazole-3-carbaldehyde 
• 65266-48-0 N-(2,2-diethoxyethyl)-N-(1,4-dimethyl-9H-carbazol-3-ylmethyl)-4-methylbenzenesulfonamide 
• 129868-40-2 9-benzyl-3-((2,2-diethoxyethyl)iminomethyl)-1,4-dimethylcarbazole 
• 74606-36-3 6-benzyl-5,11-dimethyl-6H-pyrido[4,3-b]carbazole 
• 129868-48-0 9-benzyl-5,8-dimethylcarbazole-3-carboxaldehyde 
• 519-23-3 ellipticine 

Relevant academic research and scientific papers

Platinum-Catalyzed Intramolecular Alkylation of Indoles with Unactivated Olefins

Reaction of 1-methy-2-(4-pentenyl)indole (1) with a catalytic amount of PtCl2 (2 mol %) in dioxane that contained a trace of HCl (5 mol %) at 60 °C for 24 h led to the isolation of 4,9-dimethyl-2,3,4,9-tetrahydro-1H-carbazole (2) in 92% yield. Platinum-catalyzed cyclization of 2-(4-pentenyl)indoles tolerated substitution at each position of the 4-pentenyl chain. Furthermore, the protocol was applicable to the synthesis of tetrahydro-β-carbolinones and was effective for cyclization of unprotected indoles. 2-(3-Butenyl)indoles underwent platinum-catalyzed cyclization with exclusive 6-endo-trig regioselectivity. Mechanistic studies established a mechanism for the platinum-catalyzed cyclization of 2-alkenyl indoles involving nucleophilic attack of the indole on a platinum-complexed olefin. Copyright

Synthetic Studies of Indoles and Related Compounds, Part 221. The Vilsmeier-Haack Reaction of N-Benzyl-1,2,3,4-tetrahydrocarbazoles and its Synthetic Application to Olivacine and Ellipticine2

Vilsmeier-Haack reaction of 9-benzyl-1,2,3,4-tetrahydrocarbazole (18a) at 120 deg C gave 9-benzyl-1-methylcarbazole-3-carbaldehyde (19a) and 9-benzyl-1-(N,N-(dimethylamino)methyl)carbazole-3-carbaldehyde (22a) in moderate yields, whereas, the same reaction at 0 deg C gave 9-benzyl-1,2,3,4-tetrahydrocarbazole-1-carbaldehyde (20a) in very good yield.The aldehyde (20a) was converted into 9-benzyl-1-methylcarbazole (21a) by another Vilsmeier-Haack reaction.This carbazole (21a) unexpectedly underwent non-regioselective formylation under similar reaction conditions to give a mixture of compound (19a) and 9-benzyl-8-methylcarbazole-3-carbaldehyde (23a).On the basis of the above results, a mechanism of the formation of the aromatic aldehyde (19a) was proposed, which involves 1,5-sigmatropic rearrangement of an N-methylidene dimethylammonium cation from the 4a-position to the 3-position as a key step.Vilsmeier-Haack reaction of 9-benzyl-1,2,3,4-tetrahydro-4-methylcarbazole (18b) at 100 deg C also gave 9-benzyl-1,4-dimethylcarbazole-3-carbaldehyde (19b) in moderate yield.The total syntheses of two antitumor alkaloids, olivacine (10) and ellipticine (11), were achieved by utilizing compounds (19a) and (19b) as key intermediates.