2805-84-7

Usage

Uses

Used in Scientific Research:
3-(Trifluoromethyl)-6,7,8,9-tetrahydro-5H-carbazole is used as an intermediate or building block for the synthesis of more complex compounds in scientific research. Its highly reactive nature makes it a valuable component in the development of new chemical entities.
Used in Pharmaceutical Industry:
3-(Trifluoromethyl)-6,7,8,9-tetrahydro-5H-carbazole is used as a key intermediate in the synthesis of pharmaceutical compounds. Its unique properties, such as high lipophilicity, can contribute to the development of new drugs with improved efficacy and stability.
Used in Chemical Synthesis:
3-(Trifluoromethyl)-6,7,8,9-tetrahydro-5H-carbazole is used as a reagent in various chemical synthesis processes. Its increased chemical and thermal stability allows for its use in the production of a wide range of chemical products.

InChI:InChI=1/C13H12F3N/c14-13(15,16)8-5-6-12-10(7-8)9-3-1-2-4-11(9)17-12/h5-7,17H,1-4H2

Upstream product

• 108-94-1 cyclohexanone 
• 368-90-1 4-(trifluoromethyl)phenylhydrazine 
• 1815-14-1 1-phenyl-2-(4-(trifluoromethyl)phenyl)diazene 
• 34913-29-6 4,4′-bis(trifluoromethyl)azobenzene 
• 110-52-1 1,4-dibromo-butane 
• 100846-24-0 5-trifluoromethyl-1H-indole 
• 2923-56-0 4-(trifluoromethyl)phenylhydrazine hydrochloride 
• 56-23-5 tetrachloromethane 
• 942-01-8 1,2,3,4-tetrahydrocarbazole 

Downstream Products

• 417710-34-0 6-(trifluoromethyl)-2,3,4,4a,9,9a-hexahydro-1H-carbazole 
• 2467-83-6 3-(trifluoromethyl)-9H-carbazole 

Relevant academic research and scientific papers

Direct Synthesis of Indoles from Azoarenes and Ketones with Bis(neopentylglycolato)diboron Using 4,4′-Bipyridyl as an Organocatalyst

Multifunctionalized indole derivatives were prepared by reducing azoarenes in the presence of ketones and bis(neopentylglycolato)diboron (B2nep2) with a catalytic amount of 4,4′-bipyridyl under neutral reaction conditions, where 4,4′-bipyridyl acted as an organocatalyst to activate the B-B bond of B2nep2 and form N,N′-diboryl-1,2-diarylhydrazines as key intermediates. Further reaction of N,N′-diboryl-1,2-diarylhydrazines with ketones afforded N-vinyl-1,2-diarylhydrazines, which rearranged to the corresponding indoles via the Fischer indole mechanism. This organocatalytic system was applied to diverse alkyl cyclic ketones, dialkyl, and alkyl/aryl ketones, including heteroatoms. Methyl alkyl ketones gave the corresponding 2-methyl-3-substituted indoles in a regioselective manner. This protocol allowed us to expand the preparation of indoles having high compatibility with not only electron-donating and electron-withdrawing groups but also N- and O-protecting functional groups.

Annulation of Indoles with 1,n-Dibromoalkanes by a Pd(II)-Catalyzed and Norbornene-Mediated Reaction Cascade

Employing 1,3-dibromopropane, 1,4-dibromobutane, and 1,5-dibromopentane as biselectrophiles, the annulation of indoles was probed in the presence of PdCl 2 (MeCN) 2 as a catalyst and norbornene as a transpositional ligand. Ring formation to a five-membered ring was observed at positions C2 and N, while annulation of a six-membered ring occurred at positions C2 and C3. The latter cascade process was successfully applied to the direct synthesis of 1,2,3,4-tetrahydrocarbazoles from indoles (11 examples, 31-68% yield). Seven-membered-ring annulation was feasible by an initial coupling at positon C2 followed by alkylation at C3.

Catalytic Oxidative Coupling Cyclization for Construction of Benzofuroindolenines under Mild Reaction Conditions

We describe iron-catalyzed oxidative coupling cyclization of tetrahydrocarbazoles or THβCs or THγCs to form benzofuroindolenines as fused polycyclic indoles. This mild, efficient and simple approach afforded a library of more than 52 complex compounds across a range of substrate classes with good to excellent yields. (Figure presented.).

A microwave-assisted, propylphosphonic anhydride (T3P) mediated one-pot Fischer indole synthesis

A rapid, mild, and high yielding protocol for the Fischer indolization of arylhydrazines with T3P under microwave irradiation is described. Significant features of this method include short reaction times and preparative ease.

Methods and compositions

Compounds, compositions and methods relating to kinesin inhibition are described herein.

Regioselective electrophilic trifluoromethylation of indolines, oxindoles and indoles in superacid

Treatment of indolines and N-acylindoles with HF/SbF5/CCl 4 yields 6-trifluoro derivatives (indole numbering) whereas indoles and oxindoles give the 5-trifluoro derivatives in good yield.

Traceless Fischer indole synthesis on the solid phase

The Fischer indole synthesis using polymer-bound hydrazines is employed as the key step for the development of a traceless indole synthesis on a solid support.