87167-61-1

Basic information

• Product Name: 9-benzyl-1-methyl-9H-carbazole-3-carbaldehyde
• CAS NO: 87167-61-1
• Molecular Weight: 299.372
• Mol File: 87167-61-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 9-benzyl-1-methyl-9H-carbazole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 9-benzyl-1-methyl-9H-carbazole-3-carbaldehyde(87167-61-1)
• EPA Substance Registry System: 9-benzyl-1-methyl-9H-carbazole-3-carbaldehyde(87167-61-1)

Safety Data

• Hazardous Substances Data: 87167-61-1(Hazardous Substances Data)

Upstream product

• 617-84-5 N-formyldiethylamine 
• 17017-63-9 9-benzyl-2,3,4,9-tetrahydro-1H-carbazole 
• 68-12-2 N,N-dimethyl-formamide 
• 87167-66-6 9-benzyl-1-methyl-9H-carbazole 
• 3760-54-1 1-pyrrolidinecarboxaldehyde 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 100-39-0 benzyl bromide 

Downstream Products

• 87167-68-8 9-benzyl-3-(1-(2,2-diethoxyethylimino)ethyl)-1-methylcarbazole 
• 87167-68-8 [1-(9-Benzyl-1-methyl-9H-carbazol-3-yl)-eth-(Z)-ylidene]-(2,2-diethoxy-ethyl)-amine 
• 87167-65-5 9-benzyl-3-(1-(N-(2,2-diethoxyethyl)-N-tosylamino)ethyl)-1-methylcarbazole 
• 484-49-1 Guatambuinine 
• 131713-53-6 N-(2,2-dimethoxypropyl)-4-methyl-N-<1-methyl-9-(phenylmethyl)-9H-carbazol-3-yl>methylbenzenesulphonamide 
• 131713-54-7 N-(4-methyl-benzenesulphonyl)-N-<1-methyl-9-(phenylmethyl)-9H-carbazol-3-yl>methylpropanamine-2-one 
• 131713-52-5 2,2-dimethoxy-N-<1-methyl-9-(phenylmethyl)-9H-carbazol-3-yl>methylpropanamine 
• 87177-15-9 9-benzyl-1-methylcarbazol-3-yl methyl ketone 
• 131713-51-4 2,2-dimethoxy-N-<1-methyl-9-(phenylmethyl)-9H-carbazol-3-ylidene>propanamine 

Relevant articles and documents

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.

THE VILSMEIER-HAACK REACTION OF N-ALKYL-1,2,3,4-TETRAHYDROCARBAZOLES AND THE SYNTHETIC APPLICATION TO OLIVACINE AND ELLIPTICINE

The mechanism of the formation of products resulting from the Vilsmeier-Haack reaction of N-alkyl-1,2,3,4-tetrahydrocarbazoles, and the synthetic application to olivacine and ellipticine, are described.