205642-01-9

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• 942-01-8 1,2,3,4-tetrahydrocarbazole 
• 98-59-9 p-toluenesulfonyl chloride 
• 108-94-1 cyclohexanone 
• 46175-80-8 2‘,3‘,4‘,5‘-tetrahydro-[1,1‘-biphenyl]-2-amine 
• 28075-50-5 cyclohex-1-en-1-yl trifluoromethane sulfonate 
• 1279722-89-2 2-(cyclopentylidenemethyl)benzenamine 
• 4545-18-0 N'-cyclohexylidene-4-methylbenzene-1-sulfonohydrazide 
• 1276113-19-9 2-(trimethylsilyl)phenyl 1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate 
• 27749-01-5 N'-cyclohexylidene-4-methyl-N-phenylbenzene-1-sulfonohydrazide 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 928-90-5 5-hexyl-1-ol 
• 442155-86-4 2-[6-(p-tolylsulfonyloxy)-1-hexynyl]nitrobenzene 
• 442155-88-6 2-[6-(p-toluenesulfonyloxy)-1-hexynyl]aniline 
• 442155-84-2 2-(6-hydroxy-1-hexynyl)nitrobenzene 

Downstream Products

• 942-01-8 1,2,3,4-tetrahydrocarbazole 

Relevant academic research and scientific papers

Electrocatalytic Dehydrogenative Cyclization of 2-Vinylanilides for the Synthesis of Indoles

Indole is prevalent in bioactive compounds and natural products. The development of efficient and sustainable methods to access this privileged structural scaffold has been a long-standing interest of synthetic chemists. Herein, we report an electrocataly

Synthesis of N-Tosylates of 4-Methoxy-1,2,3,4-tetrahydrocarbazole and 2-(6-Methoxy-1-cycloalken-1-yl)anilines

The reaction of N-tosylates of 2-(1-cycloalken-1-yl)anilines and 2,3,9a,9-tetrahydro-1H-carbazole with methanol in the presence of CuBr2 proceeds with high regioselectivity leading to the corresponding tosylates of 2-(6-methoxy-1-cycloalken-1-y

Iodine(III) Reagent-Mediated Intramolecular Amination of 2-Alkenylanilines to Prepare Indoles

A variety of 3-substituted and 2,3-disubstituted indoles were synthesized efficiently in good yields through the intramolecular amination of 2-alkenylanilines promoted by readily available iodine(III) reagents in a short reaction time. Mechanistic studies showed that the reaction pathway went through a nitrenium ion and that 3-acetoxy indoline was the key intermediate in the indole formation. The indole product was easily prepared on a gram scale and amination also proceeded smoothly using catalytic 3,5-dimethylphenyl iodine in the presence of mCPBA. Furthermore, the indolo[3,2-a]carbazole scaffold was prepared in good yield in six steps from commercial ortho-iodoaniline. (Figure presented.).

Selenium-catalyzed oxidative c(sp2)-h amination of alkenes exemplified in the expedient synthesis of (Aza-)indoles

A new selenium-catalyzed protocol for the direct, intramolecular amination of C(sp2)-H bonds using N-fluorobenzenesulfonimide as the terminal oxidant is reported. This method enables the facile formation of a broad range of diversely functionalized indoles and azaindoles derived from easily accessible ortho-vinyl anilines and vinylated aminopyridines, respectively. The procedure exploits the pronounced carbophilicity of selenium electrophiles for the catalytic activation of alkenes and leads to the formation of C(sp2)-N bonds in high yields and with excellent functional group tolerance.

Silver(I)-mediated C-H amination of 2-alkenylanilines: Unique solvent-dependent migratory aptitude

A highly effective silver(I)-mediated C-H amination of 2-alkenylanilines has been developed to afford a diverse range of substituted indoles. High functional group tolerance, broad substrate scope, simple/fast/high-yielding reaction, and recovery/reuse of the inexpensive silver oxidant are noteworthy. Furthermore, an uncommon migratory process of β-monosubstituted 2-alkenylanilines with solvent-dependence was demonstrated.

Continuous-flow synthesis of trimethylsilylphenyl perfluorosulfonate benzyne precursors

2-(Trimethylsilyl)phenyl perfluorosulfonated aryne precursors may now be accessed using flow chemistry, enabling the fast preparation of pure compounds with no requirement for low temperature lithiation or column chromatography. The process has been adapted to novel nonaflate precursors, utilizing the cheaper and more user-friendly nonaflyl fluoride reagent. The resultant nonaflates are shown to successfully participate in a range of aryne reaction classes.

A total synthesis of (±)-α-cyclopiazonic acid using a cationic cascade as a key step

The indole alkaloid α-cyclopiazonic acid 1 has been synthesised by a route, which features at its core an acid-catalysed cationic cascade cyclisation terminated by a sulfonamide group.

The benzyne Fischer-indole reaction

A new approach to the Fischer-indole synthesis is reported that uses the reactive intermediate benzyne. The addition of N-tosyl hydrazones to arynes, generated through fluoride activation of 2-(trimethylsilyl)phenyl triflate precursors, leads to efficient

Palladium-catalyzed tandem alkenyl and aryl C-N bond formation: A cascade N-annulation route to 1-functionalized indoles

(Chemical Equation Presented) A single tandem operation allows rapid access to a variety of substituted N-functionalized indoles. The nitrogen atom of the indole nucleus is incorporated through Pd-catalyzed aryl and alkenyl C-N bond-forming reactions (see scheme; dba = dibenzylideneacetone). Amine, aniline, amide, carbamate, and sulfonamide functional groups can be introduced efficiently.

Development of an Efficient Procedure for Indole Ring Synthesis from 2-Ethynylaniline Derivatives Catalyzed by Cu(II) Salts and Its Application to Natural Product Synthesis

The development of efficient methods for the indole synthesis catalyzed by Cu(II) salts and its applications were investigated. Cu(OAc)2 has been proved to be the best catalyst for the synthesis of various 1-p-tolylsulfonyl or 1-methylsulfonylindoles, which have both electron-withdrawing and electron-donating groups on the aromatic ring and C2 position of indoles. For the primary aniline derivatives, Cu(OCOCF 3)2 showed good activities, while Cu(OAc)2 was a good catalyst for the cyclization of secondary anilines. This methodology could be applied to the sequential cyclization reaction for the compounds which have the electrophilic part in the same molecule. By prior treatment with KH, the sequential cyclization was realized to provide the tricyclic ring systems, but it was limited to five- and six-membered rings for the second cyclization. Finally, formal and total synthesis of hippadine with the Cu(II)-promoted indole synthesis as the key step was accomplished.