5457-28-3

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
3-Cyanoindole is used as a reactant for the preparation of a variety of compounds with potential therapeutic applications. Its reactivity and structural features make it suitable for the synthesis of:
Tryptophan dioxygenase inhibitors, such as pyridyl-ethenyl-indoles, which have potential as anticancer and immunomodulatory agents.
Inhibitors of the C-terminal domain of RNA polymerase II, which possess antitumor activities and can be used in cancer treatment.
4-Substituted β-lactams, a class of antibiotics with broad-spectrum antimicrobial properties.
Biologically active indoles, which have diverse pharmacological effects and can be used in the development of new drugs.
Inhibitors of glycogen synthase kinase 3β (GSK-3), which are involved in the regulation of various cellular processes and have potential applications in the treatment of neurodegenerative diseases and other conditions.
HIV-1 integrase inhibitors, which can be used in the development of antiretroviral therapies for the treatment of HIV/AIDS.
Indole fragments as inosine monophosphate dehydrogenase (IMPDH) inhibitors, which have potential applications in the treatment of cancer and viral infections.
Used in Organic Synthesis and Chemical Research:
3-Cyanoindole is also used as a reactant in various organic synthesis reactions, such as:
Intramolecular oxidative C-H coupling reactions, which have applications in medium-ring synthesis techniques and the preparation of complex molecular structures.
The synthesis of the aziridinomitosene skeleton, which is a key structural motif in the development of novel antiviral agents and other bioactive compounds.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 5, p. 656, 1973Tetrahedron, 50, p. 6549, 1994 DOI: 10.1016/S0040-4020(01)89685-XTetrahedron Letters, 18, p. 4417, 1977 DOI: 10.1016/S0040-4039(01)83524-3

InChI:InChI=1/C10H8N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5H2

Upstream product

• 19747-79-6 ethylimino ester of indole-3-carboxylic acid 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 93609-74-6 Benzenesulfonyl-(1H-indol-3-yl)-methanone oxime 
• 19747-78-5 indole-3-carboxylic acid ethyl imido ester hydrochloride 
• 2592-05-4 1H-indole-3-carboxaldehyde oxime 
• 21978-63-2 1H-benzo[d][1,2,3]triazol-1-yl 4-methanebenzenesulfonate 
• 700-06-1 indole-3-carbinol 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 859205-33-7 1-[(4-methylphenyl)sulfonyl]-1H-indole-3-carbonitrile 
• 83-34-1 3-Methylindole 

Downstream Products

• 1670-85-5 1H-indole-3-carboxamide 
• 771-50-6 1H-indole-3-carboxylic acid 
• 19747-79-6 ethylimino ester of indole-3-carboxylic acid 
• 59108-90-6 1H-indole-3-carbothioamide 
• 74862-25-2 methyl imino ester hydrochloride of 3-indolecarboxylic acid 
• 82075-98-7 3-[3-(4-Chloro-phenyl)-[1,2,4]oxadiazol-5-yl]-1H-indole 
• 82075-99-8 3-(3-m-Tolyl-[1,2,4]oxadiazol-5-yl)-1H-indole 
• 90539-80-3 1-benzoyl-3-cyanoindole 
• 82075-97-6 5-(1H-indol-3-yl)-3-phenyl-1,2,4-oxadiazole 
• 88172-21-8 3-[3-(4-Nitro-phenyl)-[1,2,4]oxadiazol-5-yl]-1H-indole 
• 22259-53-6 3-aminomethylindole 
• 95649-37-9 N'-hydroxy-1H-indole-3-carboximidamide 
• 473918-44-4 1-phenyl-1H-indole-3-carbonitrile 
• 99532-56-6 1-(benzenesulfonyl)-1H-indole-3-carbonitrile 

Relevant academic research and scientific papers

Photocatalytic Conversion of Benzyl Alcohols/Methyl Arenes to Aryl Nitriles via H-Abstraction by Azide Radical

This report presents the visible-light-assisted synthesis of aryl nitriles from easily accessible alcohols or methyl arenes in the presence of O2. Organic photoredox catalyst, 4CzIPN (1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene), induces single electron transfer (SET) from azide N3? and generates azide radical N3?.The photogenerated N3? abstracts H atom from α-C?H bond of benzylic system, which provides aldehyde and hydrazoic acid (HN3) in situ. This reaction subsequently forms azido alcohol intermediate that transforms into nitrile with the assistance of triflic acid (Br?nsted acid). A range of alcohols and methyl arenes successfully underwent cyanation at room temperature with good to excellent yields and showed good functional group tolerance.

A NaH-promoted N-detosylation reaction of diverse p-toluenesulfonamides

A NaH-mediated detosylation reaction of various Ts-protected indoles, azaheterocycles, anilines and dibenzylamine was reported. The method features cheap reagent, convenient operations, mild reaction conditions and broad substrate scope. Moreover, this study revealed that the loading of NaH in tosylation reactions of nitrogen-containing compounds with NaH as a base in DMA or DMF should be controlled due to the possibility of adverse detosylation.

Electron Transfer Photoredox Catalysis: Development of a Photoactivated Reductive Desulfonylation of an Aza-Heteroaromatic Ring

Herein, we report a protocol for desulfonylation of aza-heteroaromatic rings via photoinduced electron transfer and hydrogen atom transfer. This general protocol has a wide substrate range and moderate to good yields. The utility of the method was demonstrated by the chemoselective desulfonylation of a molecule containing both an aliphatic and an aromatic sulfonamide. (Figure presented.).

Synthesis of sufamides of indole series

The reaction of indoles with chlorosulfonyl isocyanate yields indolylcarbonylsulfamoyl chlorides. Their reaction with amines afforded a series of indole-containing sulfamides.

A simple synthesis of nitriles from aldoximes

Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction with lH-benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU in CH2CI2, THF, or DMF. As an alternative reagent that eliminates the formation of hexamethylphosphoramide as a byproduct, use of lH-benzotriazol-lyl-4-methylbenzenesulfonate (Bt-OTs) and DBU was investigated. Reactions with this reagent also proceeded smoothly and in good yields, although in one case N-sulfonylation was observed. An attempt to gain mechanistic insight into the BOP-mediated reaction has been made using 31P{ 1H} NMR. However, no phosphorus-bearing intermediate could be readily observed. Finally, the method has been applied to the synthesis of an antiviral 4'-cyano adenosine analogue from a commercial precursor using a single saccharide protecting group.

Study of the reactions of four indolic 1-azadienes with a few enoic, ynoic, and azo dienophiles

Four indolic 1-azadienes (1a-c, 2) underwent Diels-Alder reaction, dienophile-catalysed addition-elimination reaction, Michael reaction or hydrolysis with three enoic, two ynoic and one azo dienophiles, leading to a γ-carboline, various 3-cyanoindoles, 3-formylindole and several nitrones.

SYNTHESIS OF FUNCTIONAL DERIVATIVES OF INDOLE-3-CARBOXYLIC ACIDS

Methods are described for the synthesis of the esters, hydrazides, amidines, N-phenylamidines, N1-phenylamidrazones, N1-acylamidrazones, and amide oximes of indole-3-carboxylic and 1-methylindole-3-carboxylic acids.

SYNTHESIS AND PROPERTIES OF AZOLES AND THEIR DERIVATIVES. 37. SYNTHESIS OF 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES CONTAINING INDOLE RADICALS

The 1,3-dipolar cycloaddition of nitrile N-oxides to indole nitriles yields 3,5-disubstituted 1,2,4-oxadiazoles containing an indole radical at the 5 position.Condensation of amidoximes with indole iminoesters hydrochlorides yields 1,2,4-oxadiazoles havin

BENZENESULPHONYLCARBONITRILE OXIDE. VI. PREPARATION AND REACTIONS OF HETEROCYCLIC SULPHONYL OXIMES

Pyrrole and indole derivatives react with benzenesulphonylcarbonitrile oxide, 1 (BSNO) generated in situ to give sulphonyl oximes without isolable isoxazoline intermediates.Furan reacts with BSNO to give isoxazoline 5b; treatment with acid affords the corresponding oxime 2b.Reduction of the sulphonyl oximes with aqueous titanium(III) chloride gives nitriles.The sulphonyl oxime 7 derived from indole reacts with tri-n-propylamine and stilbene to give isoxazoline 10.