61822-18-2

Usage

Uses

Used in Pharmaceutical Industry:
2,7-Dimethoxy-9H-Carbazole is used as a pharmaceutical compound for its potential therapeutic properties. Being a carbazole alkaloid, it may have bioactive properties that can be harnessed for the development of new drugs or treatments.
Used in Chemical Research:
2,7-Dimethoxy-9H-Carbazole can be utilized as a research compound in the field of organic chemistry. Its unique structure may provide insights into the synthesis of new compounds or the study of chemical reactions involving carbazole alkaloids.
Used in Natural Product Extraction:
As a naturally occurring compound found in Clausena excavata, 2,7-Dimethoxy-9H-Carbazole can be used in the extraction and purification processes of natural products. This may lead to the discovery of new bioactive compounds with potential applications in various industries.

Upstream product

• 92248-06-1 3-methoxy-N-(3-methoxyphenyl)benzenamine 
• 5344-78-5 4-bromo-3-nitroanizole 
• 96-96-8 4-methoxy-2-nitroaniline 
• 5720-07-0 4-methoxyphenylboronic acid 
• 67-56-1 methanol 
• 124-41-4 sodium methylate 
• 136630-39-2 2,7-dibromo-9H-carbazole 
• 1424799-08-5 1-benzyl-6-methoxy-1H-indole-2-carbaldehyde 
• 1424799-09-6 1-(1-benzyl-6-methoxy-1H-indol-2-yl)-2-methoxybuta-2,3-dien-1-ol 
• 1424799-10-9 9-benzyl-2,7-dimethoxy-9H-carbazole 
• 536-90-3 m-Anisidine 
• 51409-74-6 3-(3-methoxyphenylamino)cyclohex-2-en-1-one 
• 82961-67-9 3-(3-methoxyphenylamino)phenol 
• 108-95-2 phenol 

Downstream Products

• 815632-42-9 2,7-dimethoxy-9-(4-methoxyphenyl)carbazole 
• 890079-92-2 2,7-dimethoxy-9-(2-methoxyphenyl)carbazole 
• 1220125-47-2 2,7-dimethoxy-N-(4-vinylphenyl)carbazole 
• 1220125-46-1 2,7-dimethoxy-N-(4-formylphenyl)carbazole 
• 1338080-13-9 2-[4-(2,7-dimethoxy-9H-carbazol-9-yl)phenyl]-5-(2,4,6-triisopropylphenyl)-1,3,4-oxadiazole 
• 1338080-12-8 2-[4-(2,7-dimethoxy-9H-carbazol-9-yl)phenyl]-5-(2,4,6-trimethylphenyl)-1,3,4-oxadiazole 
• 1338080-15-1 2-[4-(2,7-dimethoxy-9H-carbazol-9-yl)phenyl]-5-methyl-1,3,4-oxadiazole 
• 1357930-01-8 C₃₂H₅₃NO₆Si₆ 
• 1556929-13-5 [2,6-dichloro-4-(2,7-dimethoxy-N-carbazolyl)phenyl]bis(2,4,6-trichlorophenyl)methyl 
• 1599431-85-2 C₃₃H₁₉Cl₈NO₂ 
• 1612774-94-3 C₂₆H₂₂N₂O₂ 

Relevant academic research and scientific papers

Fine-tuning hydroxylamines as single-nitrogen sources for Pd(0)-catalyzed diamination of o-bromo(or chloro)-biaryls

Transition metal-catalyzed diamination by hydroxylamines is a common approach for making three-membered aziridines, while its use for building the larger N-heterocycles is still underdeveloped. Herein, we report an efficient Pd(0)-catalyzed inter-molecular [4+1] annulation of o-bromo(or chloro)-biaryls with bifunctional secondary hydroxylamines for the one-step assembly of synthetically useful carbazoles. Noteworthily, a linchpin for this domino reaction was the judicious selection of both the amino-sources and Pd(0)-catalysts for enabling the prerequisite oxidative addition of aryl halides to Pd(0)-species in the presence of hydroxylamines with a labile N-O bond. [Figure not available: see fulltext.].

Site-Specific Synthesis of Carbazole Derivatives through Aryl Homocoupling and Amination

We synthesized various carbazoles from anilines through a three-step process with good overall yields (up to 48percent). This process comprises N -acetylation, copper(0)-mediated Ullmann homocoupling, and acid-mediated intramolecular amination. It permits various functional groups on the substrate. Scale-up of the developed three-step synthetic route to carbazoles was also demonstrated.

"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.

Biphilic Organophosphorus-Catalyzed Intramolecular Csp2-H Amination: Evidence for a Nitrenoid in Catalytic Cadogan Cyclizations

A small-ring phosphacycloalkane (1,2,2,3,4,4-hexamethylphosphetane, 3) catalyzes intramolecular C-N bond forming heterocyclization of o-nitrobiaryl and -styrenyl derivatives in the presence of a hydrosilane terminal reductant. The method provides scalable access to diverse carbazole and indole compounds under operationally trivial homogeneous organocatalytic conditions, as demonstrated by 17 examples conducted on 1 g scale. In situ NMR reaction monitoring studies support a mechanism involving catalytic PIII/PV=O cycling, where tricoordinate phosphorus compound 3 represents the catalytic resting state. For the catalytic conversion of o-nitrobiphenyl to carbazole, the kinetic reaction order was determined for phosphetane catalyst 3 (first order), substrate (first order), and phenylsilane (zeroth order). For differentially 5-substituted 2-nitrobiphenyls, the transformation is accelerated by electron-withdrawing substituents (Hammett factor ? = +1.5), consistent with the accrual of negative charge on the nitro substrate in the rate-determining step. DFT modeling of the turnover-limiting deoxygenation event implicates a rate-determining (3 + 1) cheletropic addition between the phosphetane catalyst 3 and 2-nitrobiphenyl substrate to form an unobserved pentacoordinate spiro-bicyclic dioxazaphosphetane, which decomposes via (2 + 2) cycloreversion giving 1 equiv of phosphetane P-oxide 3·[O] and 2-nitrosobiphenyl. Experimental and computational investigations into the C-N bond forming event suggest the involvement of an oxazaphosphirane (2 + 1) adduct between 3 and 2-nitrosobiphenyl, which evolves through loss of phosphetane P-oxide 3·[O] to give the observed carbazole product via C-H insertion in a nitrene-like fashion.

Visible-Light-Induced Synthesis of Carbazoles by in Situ Formation of Photosensitizing Intermediate

A visible-light-induced synthesis of N-H carbazoles from easily accessible 2,2′-diaminobiaryls in the absence of any external photosensitizer is reported. The process only requires tBuONO and natural resources, visible light, and molecular oxygen for the synthesis of N-H carbazoles. Experimental and computational studies support that the in situ formation of a visible-light-absorbing photosensitizing intermediate, benzocinnoline N-imide, is responsible for the activation of triplet molecular oxygen to singlet oxygen that, in turn, promotes the synthesis of carbazole.

Chemoselective arylation of phenols with bromo-nitroarenes: Synthesis of nitro-biaryl-ols and their conversion into benzofurans and carbazoles

A series of electron withdrawing or donating group substituted phenols were chemoselectively arylated with various substituted bromo-nitroarenes using KOtBu at room temperature via an SNAr pathway. The synthesis of natural alkaloids (carbazoles), dibenzofurans, and a biaryl-indole was achieved from the synthesized nitro-biaryl-ols. This journal is the Partner Organisations 2014.

Ruthenium-catalyzed cross-dehydrogenative ortho-N-carbazolation of diarylamines: Versatile access to unsymmetrical diamines

The dehydrogenative C-N cross-coupling of unprotected, secondary anilines through ortho-N-carbazolation has been achieved using a Ru catalytic system with O2 as the terminal oxidant. The reactions proceed in an intermolecular fashion, selectively in the ortho position. Implications for the field of organic synthesis are discussed. No-No-No: Amination of a non-acidic Ci￡H bond, no pre-activation of the coupling partners, no chelate-assisting directing group. Dehydrogenative C-N cross-coupling through the ortho-N-carbazolation of unprotected, secondary anilines has been achieved using a Ru catalyst with O2 as the terminal oxidant. The reactions proceed in an intermolecular fashion, selectively in the ortho position.

Rapid synthesis of fused N-heterocycles by transition-metal-free electrophilic amination of arene C-H bonds

We disclose an efficient and operationally simple protocol for the preparation of fused N-heterocycles starting from readily available 2-nitrobiaryls and PhMgBr under mild conditions. More than two dozen N-heterocycles, including two bioactive natural products, have been synthesized using this method. A stepwise electrophilic aromatic cyclization mechanism was proposed by DFT calculations. Controlled fusion: A transition-metal-free, low-temperature, and regioselective intramolecular amination of aromatic C(sp2)-H bonds provides fused N-heterocycles. This reaction is operationally simple and scalable (1-10 mmol) and the scope of substrates is wide (see scheme). Density functional calculations indicate that a stepwise electrophilic aromatic cyclization mechanism may be operative.

Palladium-catalyzed synthesis of natural and unnatural 2-, 5-, and 7-oxygenated carbazole alkaloids from N-arylcyclohexane enaminones

A palladium-catalyzed synthesis of the carbazole framework is described, including the preparation of 2-, 5-, and 7-oxygenated natural and unnatural carbazole alkaloids. A series of N-arylcyclohexane enaminones, generated by condensation of cyclohexane-1,3-dione with diverse anilines, were aromatized by a Pd(0)-catalyzed thermal treatment to afford the corresponding diarylamines. The latter were submitted to a Pd(II)-catalyzed cyclization and methylation processes to provide the desired carbazoles, including clausine V. Following an inverse strategy, a new and short total synthesis of glycoborine is also reported.

An efficient Au-catalyzed synthesis of isomukonidine, clausine L, mukonidine, glycosinine, mukonal, and clausine v from propadienyl methyl ether

Naturally occurring carbazole alkaloids such as isomukonidine, clausine L, mukonidine, glycosinine, mukonal, and clausine V have been synthesized through a gold-catalyzed cyclization reaction of 1-(indol-2-yl)-2-methoxy-2,3-allenols, which are readily available from indolecarbaldehydes and methoxypropadiene. Compared to the reported procedures, our approach is general, atom economic, highly selective, and the starting materials are easily available.