24075-48-7

Upstream product

• 4630-20-0 3-Methyl-9H-carbazole 
• 77-78-1 dimethyl sulfate 
• 21240-56-2 9-methyl-9H-carbazole-3-carbaldehyde 
• 144463-81-0 allyl N-methyl-N-(4-methylphenyl)anthranilate 
• 1158986-73-2 C₁₆H₁₉NO₂ 
• 1158986-67-4 1-methyl-2-(3-methyl-3-butenyl)-1H-indole 
• 64-19-7 acetic acid 
• 38158-65-5 N,4-dimethyl-N-phenylaniline 
• 624-31-7 4-tolyl iodide 
• 100-61-8 N-methylaniline 
• 1410070-97-1 2-iodo-N-(p-tolyl)aniline 
• 34058-63-4 3-(methylthio)-9-methyl-9H-carbazole 
• 75-16-1 methylmagnesium bromide 
• 16524-23-5 N-p-tolyl-anthranilic acid 

Relevant academic research and scientific papers

Redox-neutral decarboxylative photocyclization of anthranilic acids

A mild metal-, catalyst-, and oxidant-free photoredox neutral system has been found to efficiently enable intramolecular decarboxylative cyclization of anthranilic acids. This facile protocol provides an alternative method for the synthesis of carbazoles. Mechanistic studies reveal a key photoinduced 6π-electrocyclization process and formic acid was released as the sole byproduct.

Method for preparing carbazole compound

The invention discloses a method for synthesizing a carbazole compound by utilizing N,N-di-substituted o-aminobenzoate compound. The synthesis method comprises the following steps of adopting a palladium salt as a catalyst, mixing the palladium salt, the N,N-di-substituted o-aminobenzoate compound, an oxidant and an organic solvent, and carrying out heating reaction to obtain the carbazole compound. The method disclosed by the invention has the advantages that the preparation route is short, the universality of a substrate is good, the synthesis yield is high, the used catalyst is simple and easy to obtain and the like.

Pd-Catalyzed Intramolecular Chemoselective C(sp2)-H and C(sp3)-H Activation of N-Alkyl- N-arylanthranilic Acids

A controllable palladium-catalyzed intramolecular C-H activation of N-alkyl-N-arylanthranilic acids has been developed. The methodology allows selective synthesis of 1,2-dihydro-(4H)-3,1-benzoxazin-4-ones and carbazoles from the same starting materials and palladium catalyst. The selectivity is controlled by the oxidant. Silver oxide promotes C(sp3)-H activation/C-O cyclization to provide 1,2-dihydro-(4H)-3,1-benzoxazin-4-ones, while copper acetate contributes to C(sp2)-H activation/decarboxylative arylation to afford carbazoles. This protocol is demonstrated by its wide substrate scope and good functional group tolerance.

Copper(II) catalyzed aromatization of tetrahydrocarbazole: An unprecedented protocol and its utility towards the synthesis of carbazole alkaloids

An efficient protocol for the aromatization of tetrahydrocarbazole is described by using catalytic copper(II) chloride dihydrate in DMSO. This newly established methodology has utilized towards the synthesis of naturally occurring carbazole alkaloids, namely 3-methylcarbazole, 3-formyl carbazole, glycozoline, glycozolicine and clauszoline-K. In addition, the protocol is generalized for the aromatization of N-substituted tetrahydrocarbazole, 1,2,3,4-tetrahydroquinoline, 1,2,3,4-tetrahydroisoquinoline and 1,2,3,4-tetrahydro β-carboline to give the corresponding heteroaromatic compounds from very good to excellent yield. Moreover, this method has been proven to be tolerant to a broad range of functional groups with excellent yields.

Ni-Catalyzed cross-coupling of aryl thioethers with alkyl Grignard reagents via C-S bond cleavage

A Ni-catalyzed cross-coupling of aryl thioethers with alkyl Grignard reagents, accompanied by the cleavage of the C(aryl)-SMe bond, has been presented. This method is distinguished by its mild conditions and moderate functional group tolerance, such as hydroxyl, halogen, and heterocycles, which should provide a straightforward access to the modification of sulfur-containing molecules.

An Expedient Synthesis of Carbazoles through Potassium tert-Butoxide-Promoted Intramolecular Direct C–H Bond Arylation

Transition-metal-free access to carbazoles was achieved through base-mediated intramolecular C–C bond formation. Reactions of N-substituted o-halodiarylamines with potassium tert-butoxide in the presence of ethylene glycol or 1,10-phenanthroline provided carbazoles in moderate to excellent yields. This transformation may proceed through a radical pathway according to a control experiment with a radical scavenger.

Photochemical Synthesis of Carbazoles Using an [Fe(phen)3](NTf2)2/O2 Catalyst System: Catalysis toward Sustainability

An increasingly sustainable photochemical synthesis of carbazoles was developed using a catalytic system of Fe(phen)3(NTf2)2/O2 under continuous flow conditions and was demonstrated on gram-scale using a numbering-up strategy. Photocyclization of triaryl and diarylamines into the corresponding carbazoles occurs in general in higher yields than with previously developed photocatalysts.

Palladium-catalyzed α-arylation of enones in the synthesis of 2-alkenylindoles and carbazoles

A new unified strategy has been developed for the synthesis of substituted 2-alkenylindoles and carbazoles. The strategy uses palladium-catalyzed α-arylation of TES-enol ethers of enones as the key step. The method is highly regioselective, provides good yields, and is expected to have wide application.

A visible-light-mediated synthesis of carbazoles

The photosynthetic preparation of N-aryl- and N-alkyl-bearing carbazoles utilizes continuous flow, visible light, and an in situ formed Cu-based sensitizer (see picture). The method is mild and efficient, and allows the straightforward synthesis of a variety of carbazoles with different substituents, heterocycles, and complex carbon architectures. Copyright

Novel palladium-catalyzed acyloxylation/cyclization of 2-(3′-alkenyl) indoles

A new and mild palladium(II)-catalyzed reaction for the intramolecular acyloxylation/cyclization of 2-(3′-alkenyl)indoles was developed. The newly formed cycles involve oxygen-containing functionalized groups, which might be transferred further to provide other indole derivatives.