18992-67-1

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 84, p. 94, 1962 DOI: 10.1021/ja00860a022Tetrahedron, 44, p. 5215, 1988 DOI: 10.1016/S0040-4020(01)86029-4Tetrahedron Letters, 27, p. 1939, 1986 DOI: 10.1016/S0040-4039(00)84417-2

Upstream product

• 79242-95-8 1,2-dimethyl-6,7,8,9-tetrahydro-5H-carbazole 
• 3484-18-2 2-ethylindole 
• 4652-27-1 4-methoxy-3-buten-2-one 
• 78-94-4 methyl vinyl ketone 
• 120211-10-1 2-(1,2-dimethyl-1-propenyl)indole 
• 68-12-2 N,N-dimethyl-formamide 
• 95-53-4 o-toluidine 
• 5541-89-9 4-(1H-indol-3-yl)-2-butanone 
• 31951-75-4 4-(1H-indol-3-yl)-but-3-en-2-one 
• 120-72-9 indole 
• 3230-69-1 3-methyl-1-penten-4-yn-3-ol 
• 854826-22-5 7,8-dimethyl-2,3,4,9-tetrahydro-carbazol-1-one 
• 822-87-7 2-Chlorocyclohexanone 
• 87-59-2 2,3-Dimethylaniline 

Relevant academic research and scientific papers

SYNTHESIS OF CARBAZOLES VIA 2-VINYLINDOLES.

2-Vinylindoles are obtained from the Fischer indolization of α,β-unsaturated ketones.Heating 2-(2-methylpropenyl)indole (4) with the Vilsmeier reagent (DMF/POCl3) gave 2-methylcarbazole in good yield, presumably via an electrocyclic ring closure of a hexatrienic intermediate.

Regioselective Cyclization of (Indol-3-yl)pentyn-3-ols as an Approach to (Tetrahydro)carbazoles

An acid-catalyzed, highly regioselective cycloisomerization as well as dehydro-cyclization of (indol-3-yl)pentyn-3-ols has been reported for the selective synthesis of tetrahydrocarbazoles and carbazoles. This process is mild and found to be very general in terms of structural diversity of substrates. Utilizing the strategy, an efficient synthetic approach for the functionalized frameworks of carbazomycins A-D has also been developed.

A Br?nsted Acid Catalyzed Cascade Reaction for the Conversion of Indoles to α-(3-Indolyl) Ketones by Using 2-Benzyloxy Aldehydes

A Br?nsted acid catalyzed, operationally simple, scalable route to several functionalized α-(3-indolyl) ketones has been developed and the long-standing regioisomeric issue has been eliminated by choosing appropriate carbonyls. A readily available and cheap bottle reagent was used as the catalyst. This protocol was also applicable to the synthesis of densely functionalized α-(3-pyrrolyl) ketones. A detailed mechanistic study confirmed the involvement of enolether as a reaction intermediate. Several postsynthetic modifications along with easy access to β-carboline, tryptamines, tryptophols, and spiro-indolenine proclaim the synthetic utility of this powerful building block. On the basis of this concept, functionalized carbazoles were constructed by a cascade annulation strategy.

Ruthenium-Catalyzed Cascade Annulation of Indole with Propargyl Alcohols

Cascade transformations forming multiple bonds and one-pot procedures provide rapid access to natural-product-like scaffolds from simple precursors. These atom-economic processes are valuable tools in organic synthesis and drug discovery. Herein, we report on ruthenium-catalyzed cascade annulations of indole with readily available propargyl alcohols. These provide rapid access to diverse carbazoles, cyclohepta[b]indoles, and further fused polycycles with high selectivity. A bifunctional ruthenium complex featuring a redox-coupled cyclopentadienone ligand acts as a common catalyst for the different cascade processes.

Ruthenium-catalyzed functionalization of pyrroles and indoles with propargyl alcohols

Several ruthenium-catalyzed atom-economic transformations of propargyl alcohols with pyrroles or indoles leading to alkylated, propargylated, or annulated heteroaromatics are reported. The mechanistically distinct reactions are catalyzed by a single ruthenium(0) complex containing a redox-coupled dienone ligand. The mode of activation regarding the propargyl alcohols determines the reaction pathway and depends on the alcohols' substitution pattern. Secondary substrates form alkenyl complexes by a 1,2-hydrogen shift, whereas the transformation of tertiary substrates involves allenylidene intermediates. 1-Vinyl propargyl alcohols are converted by a cascade allylation/cyclization sequence. The environmentally benign processes are of broad scope and allow the selective synthesis of highly functionalized pyrroles and indoles generating water as the only waste product. Copyright

A NEW SYNTHESIS OF 1,2-DISUBSTITUED CARBAZOLES. ELECTROPHILIC CYANATION WITH VIEHE'S REAGENT.

Reaction of 2-ethylindole and 2-benzylindole with methyl vinyl ketone gives 1,2-dimethylcarbazole and 2-methyl-1-phenylcarbazole respectively.On thermolysis of the salt 11, obtained from the reaction of 2-(2-methylpropenyl)indole (7a) with Viehe's salt (10), the corresponding nitrile 13 is formed.

The Chemistry of Carbazoles. VII. Syntheses of Methylcarbazoles

Thirty-six methylcarbazoles were prepared, and their synthetic methods were critically described.