3652-91-3

Usage

Synthesis Reference(s)

Tetrahedron, 44, p. 5215, 1988 DOI: 10.1016/S0040-4020(01)86029-4

InChI:InChI=1/C13H11N/c1-9-6-7-11-10-4-2-3-5-12(10)14-13(11)8-9/h2-8,14H,1H3

Upstream product

• 95-20-5 2-methyl-1H-indole 
• 78-94-4 methyl vinyl ketone 
• 123-31-9 hydroquinone 
• 21240-53-9 7-methyl-2,3,4,9-tetrahydro-1H-carbazole 
• 6286-54-0 2-methyl-1,2,3,4-tetrahydro-9H-carbazole 
• 4652-27-1 4-methoxy-3-buten-2-one 
• 1205-64-7 3-Methyldiphenylamine 
• 104706-67-4 Dimethyl-[2-(2-methyl-propenyl)-1H-indol-3-ylmethylene]-ammonium 
• 3417-69-4 2-(2-methylprop-1-enyl)-1H-indole 
• 68-12-2 N,N-dimethyl-formamide 
• 108-44-1 1-amino-3-methylbenzene 
• 822-87-7 2-Chlorocyclohexanone 
• 73910-75-5 7-methyl-1-oxo-1,2,3,4-tetrahydrocarbazole 
• 91901-92-7 4-Methyl-2-azidobiphenyl 

Downstream Products

• 152499-78-0 9-benzoyl-2-methylcarbazole 
• 116325-34-9 2-methyl-9-benzenesulfonylcarbazole 
• 126479-88-7 9-benzenesulfonyl-2-carbazolecarboxaldehyde 
• 126479-86-5 2-dibromomethyl-9-benzenesulfonylcarbazole 
• 126479-91-2 9-benzenesulfonyl-2-(2-naphthylethenyl)carbazole 
• 126479-90-1 9-benzenesulfonyl-2-(1-naphthylethenyl)carbazole 
• 126479-97-8 9-benzenesulfonyl-2-(2-naphthylethyl)carbazole 
• 126479-96-7 9-benzenesulfonyl-2-(1-naphthylethyl)carbazole 
• 152499-81-5 2-Acetylamino-2-(9-benzoyl-9H-carbazol-2-ylmethyl)-malonic acid diethyl ester 
• 152499-79-1 9-benzoyl-2-bromomethylcarbazole 

Relevant academic research and scientific papers

Benzoannelation of 2-methylindole via 1-N-carboxy-2-methylindole dianion: A direct regiospecific route to substituted and annelated carbazoles

A facile general route for substituted and annelated N-H- carbazoles 6 has been developed by regiospecific 1,2-addition of 1- N-carboxy-2-methylindole dianion 3 to acyclic and cyclic α-oxoketene dithioacetals 4 followed by cycloaromatization in the presence of H3PO4.

Visible-light-driven Cadogan reaction

Visible-light-driven photochemical Cadogan-type cyclization has been discovered. The organic D-A type photosensitizer 4CzIPN found to be an efficient mediator to transfer energy from photons to the transient intermediate that breaks the barriers of deoxygenation in Cadogan reaction and enables a mild metal-free access to carbazoles and related heterocycles. DFT calculation results indicate mildly endergonic formation of the intermediate complex of nitrobiarenes and PPh3, which corresponds with experimental findings regarding reaction temperature. The robust synthetic capacity of the photoredox Cadogan reaction systems has been demonstrated by the viable productivity of a broad range of carbazoles and related N-heterocycles with good tolerance of various functionalities.

Convenient One-Pot Synthesis of 9 H -Carbazoles by Microwave Irradiation Employing a Green Palladium-Based Nanocatalyst

An efficient palladium-catalyzed tandem reaction for the one-pot synthesis of 9 H -carbazoles under microwave irradiation is developed. This approach involves a sequential Buchwald-Hartwig amination and a direct arylation from affordable and inexpensive anilines and 1,2-dihaloarenes. For the development of this purpose, a novel and magnetically recoverable palladium nanocatalyst supported on a green biochar under ligand-free conditions is used. Compared to other existing palladium-based protocols, the present synthetic methodology shows a drastic reduction in reaction times and excellent compatibility with different functional groups allowing to obtain a small library of 9 H -carbazoles in high yields and with good regioselectivity. This procedure represents the first example in the direct synthesis of carbazoles using a heterogeneous palladium nanocatalyst from commercial precursors. To examine the application of this protocol, a direct and scalable synthesis of the bioactive carbazole alkaloid clausenalene from commercially available starting materials is described.

Total synthesis of carbazole alkaloids

A Suzuki-Miyaura cross coupling, followed by triphenylphosphine mediated Cadogan reductive cyclization sequence provided efficient access to a series of carbazole alkaloids. In the present work, this approach was applied to the total synthesis of mukonine, clauszoline K, koenoline, murrayanine, murrayafoline A, mukoeic acid, glycoborine, glycozolicine, mukolidine, mukoline, glycozoline, 3-methoxy-9H-carbazole-1-carboxylic acid methyl ester, (3-methoxy-9H-carbazol-1-yl)-methanol, 3-methoxy-9H-carbazole-1-carbaldehyde, 3-methoxy-9H-carbazole-1-carboxylic acid, 2-methyl-9H-carbazole and nonsteroidal anti-inflammatory drug (NSAID) carprofen and its derivatives.

Metal-free deoxygenation and reductive disilylation of nitroarenes by organosilicon reducing reagents

A metal-free deoxygenation and reductive disilylation of nitroarenes was achieved using N,N’-bis(trime-thylsilyl)-4,4’-bipyridinylidene (1) under mild and neutral reaction conditions, and a broad functional group tolerance was possible in this reaction. Mono-deoxygenation, giving a synthetically valuable N,O-bis(trimethylsilyl)phe-nylhydroxylamine (7a) as a readily available and safe phenylnitrene source from nitrobenzene, and double-deoxy-genation, giving N,N-bis(trimethylsilyl)anilines 8, were easily controlled by varying the amounts of 1 and reaction temperature as well as adding dibenzothiophene (DBTP). Reaction of 2-arylnitrobenzenes with 1 resulted in the formation of the corresponding carbazoles 14 via in situ-gen-erated phenylnitrene species derived by thermolysis of N,O-bis(trimethylsilyl)phenylhydroxylamines 7, followed by their subsequent intramolecular C H insertion. In addition, the intramolecular N N coupling reaction proceeded in the reduction of 2,2’-dinitrobiphenyl derivatives by 1, giving the corresponding benzo[c]cinnolines.

A Combined Tamaru Allylation/Olefin Cross-Metathesis Approach for the Total Syntheses of (±)-Paniculidine B, (±)-Paniculidine C, and 2-Methylcarbazole

A concise approach to the total syntheses of racemic paniculidines B and C is described. The route features a combined Tamaru allylation/olefin cross-metathesis sequence for the regiocontrolled synthesis of prenylindole intermediates. In addition, we report a transformation of the prenylated indole into 2-methylcarbazole catalyzed by sulfonic acid-functionalized silica gel.

Preparation of 2 - substituted oxazole compounds

The present invention belongs to the field of organic chemistry, and particularly relates to a preparation method for 2-substituted carbazole compounds. According to the preparation method provided by the present invention, the raw material source is wide, reaction operation and post-treatment are simple and convenient, the yield is high, the application range is wide, and the industrial production is facilitated.

Photochemical intramolecular amination for the synthesis of heterocycles

Polycyclic heterocycles can be formed in good to excellent yields via photochemical conversion of the corresponding substituted aryl azides under irradiation with purple LEDs in a continuous flow reactor. The experimental set-up is tolerant to UV-sensitive functional groups while affording diverse carbazoles, as well as an indole and pyrrole framework, in short reaction times. The photochemical method is presumed to progress through a mechanism differing from the other methods of azide activation involving transition metal catalysis.

Synthetic method of carbazole and derivatives thereof

The invention discloses a synthetic method of carbazole and derivatives thereof. The synthetic method is characterized in that the carbazole and derivatives thereof are obtained by N-substituted reaction, vinylation reaction, removal of R2 group and olefin closed-loop double decomposition reaction. According to the synthetic method of the carbazole and derivatives thereof, disclosed by the invention, various derivatives of the carbazole can be synthesized according to substituent groups on indole rings of raw materials; in addition, no substituent group is formed on N of the carbazole; the substituent group can be used as an intermediate as required for next-step synthesis. Meanwhile, according to the synthetic method disclosed by the invention, the carbazole and derivatives thereof are synthesized by using the raw materials with abundant sources, and further the huge demand of the carbazole and derivatives thereof is met. Besides, a synthetic route is simple, reaction conditions are easily controlled and realized, the yield of a product is high, and higher practicality is realized.

Nickel-catalyzed methylation of aryl halides/tosylates with methyl tosylate

This work describes the cross-electrophile methylation of aryl bromides and aryl tosylates with methyl tosylate. The mild reaction conditions allow effective methylation of a wide set of heteroaryl electrophiles and dimethylation of dibromoarenes.