74606-36-3

Upstream product

• 519-23-3 ellipticine 
• 100-39-0 benzyl bromide 
• 129868-41-3 9-benzyl-3-((N-(2,2-diethoxyethyl)-N-tosylamino)methyl)-1,4-dimethylcarbazole 
• 17017-64-0 9-benzyl-4-methyl-2,3,4,9-tetrahydro-1H-carbazole 
• 19283-50-2 4-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one 
• 62334-20-7 2-hydroxymethylene-4-methylcyclohexanone 
• 18028-55-2 1,4-dimethyl-9H-carbazole 
• 100-44-7 benzyl chloride 
• 589-92-4 1-methylcyclohexan-4-one 
• 129868-52-6 (9-Benzyl-3-formyl-4-methyl-9H-carbazol-1-ylmethyl)-trimethyl-ammonium; iodide 
• 129868-40-2 9-benzyl-3-((2,2-diethoxyethyl)iminomethyl)-1,4-dimethylcarbazole 
• 129868-47-9 9-benzyl-1-((N,N-dimethylamino)methyl)-4-methylcarbazole-3-carbaldehyde 
• 129868-46-8 9-benzyl-1,2,3,4-tetrahydro-4-methylcarbazole-1-carbaldehyde 
• 87167-62-2 9-benzyl-1,4-dimethyl-9H-carbazole-3-carbaldehyde 

Downstream Products

• 519-23-3 ellipticine 
• 85619-30-3 6-benzyl-2-carboethoxy-1-cyano-1,2-dihydroellipticine 
• 74606-39-6 2-benzoyl-6-benzyl-1-cyano-1,2-dihydroellipticine 
• 85619-21-2 2-Benzenesulfonyl-6-benzyl-5,11-dimethyl-2,6-dihydro-1H-pyrido[4,3-b]carbazole-1-carbonitrile 
• 85619-19-8 6-benzyl-2-(4-chlorobutanoyl)-1-cyano-1,2-dihydroellipticine 
• 85619-24-5 2-benzoyl-6-benzyl-1-(p-benzyloxybenzyl)-1-cyano-1,2-dihydroellipticine 
• 85619-25-6 2-benzoyl-6-benzyl-1-cyano-1-(m-trifluoromethylbenzyl)-1,2-dihydroellipticine 
• 85619-22-3 2-benzoyl-6-benzyl-1-cyano-1-ethyl-1,2-dihydroellipticine 
• 85619-26-7 1-Allyl-2-benzoyl-6-benzyl-5,11-dimethyl-2,6-dihydro-1H-pyrido[4,3-b]carbazole-1-carbonitrile 
• 85619-06-3 6-benzyl-1-(m-trifluoromethylbenzyl)ellipticine 
• 85619-05-2 6-benzyl-1-(p-bromobenzyl)ellipticine 
• 85619-29-0 6-benzylellipticine-1-carboxamide 
• 85619-11-0 6-benzyl-1-cyanoellipticine 
• 85619-03-0 6-benzyl-1-ethylellipticine 

Relevant academic research and scientific papers

Friedel-crafts cyclodehydration approach toward the synthesis of ellipti-cine and 9-methoxyellipticine

An expedient synthesis of biologically important pyrido[4,3-b]carbazole alkaloids, ellipticine and 9-methoxyellipticine, is reported. Our synthetic approach applies a key H3PO4-mediated Friedel-Crafts cyclodehydration to construct the pyridine core.

Reaction of l-benzylindole-2,3-dicarboxylic anhydride with 3-bromo-4-lithiopyridine: Formal synthesis of ellipticine

Reaction of l-benzylindole-2,3-dicarboxylic anhydride with 3-bromo-4-lithiopyridine gave 2-(3-bromoisonicotinoyl)indole-3-carboxylic acid as the sole product. The indole-3-carboxylic acid could be converted to 6-benzylellipticine quinone in five steps.

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.