Chemistry Heterocyclic building blocks Indoles 1h-indole-2-carbonitrile

1h-indole-2-carbonitrile

These compounds have the same murcko framework: 1H-indole-2-carbonitrile

Nucleophilic Substitution: The cyano group is a good leaving group. Under suitable conditions, the nitrogen in the cyano group can be replaced by a nucleophile. For example, it might react with a strong nucleophile to form a substitution product.
Reduction: The cyano group (–CN) can be reduced to the corresponding amine (–NH2) using reducing agents such as LiAlH4 or NaBH4.
Indole Ring Reactions: The indole ring is aromatic and can undergo electrophilic aromatic substitution reactions. For instance, it may react with electrophiles like acids, acyl halides, or nitration reagents.
Nitrile Hydrolysis: Under acidic or basic conditions, the cyano group can undergo hydrolysis to form a carboxylic acid or its salt.
Amidation Reactions: The cyano group can react with amines or ammonia to form amides.
Cyanation Reactions: The indole-2-carbonitrile can undergo reactions where the cyano group is used to introduce a nitrile group into another molecule.
Grignard Reactions: The indole-2-carbonitrile may react with a Grignard reagent to form a new carbon-carbon bond.
Metalation Reactions: The hydrogen on the indole nitrogen can be replaced with a metal group, making it reactive towards various electrophiles.
Cyclization Reactions: Depending on the reaction conditions, the compound may undergo cyclization reactions to form fused ring systems or other cyclic structures.
Oxidation Reactions: The compound can undergo oxidation reactions under suitable conditions, converting the indole nitrogen to a more oxidized state.

Further Reading:

Framework+−

(1-(tert-butoxycarbonyl)-1h-indol-2-yl)boronic acid (1h-indol-2-yl)boronic acid (1h-indol-2-yl)methanol (3as,7as)-octahydro-1h-indole (9h-fluoren-9-yl)methyl (2-(1h-indol-3-yl)ethyl)carbamate 1,2,3,4-tetrahydrocyclopenta[b]indole 1,2-dimethyl-1h-indole 1-(1h-indol-1-yl)ethan-1-one 1-(1h-indol-3-yl)ethan-1-one 1-(phenylsulfonyl)-1h-indole 1-(triisopropylsilyl)-1h-pyrrolo[2,3-b]pyridine 1-benzyl-1h-indole 1-ethyl-1h-indole 1-methyl-1h-indole 1-methyl-1h-indole-2-carboxylic acid 1-methyl-1h-indole-3-carbaldehyde 1-methyl-1h-pyrrolo[2,3-b]pyridine 1-phenyl-1h-indole 1h-indol-3-ol 1h-indol-3-yl acetate 1h-indol-4-amine 1h-indol-4-ol 1h-indol-5-ol 1h-indol-6-amine 1h-indol-6-ol 1h-indol-7-amine 1h-indole-2-carbaldehyde 1h-indole-2-carbonitrile 1h-indole-3-carbonitrile 1h-indole-3-carboxylic acid 1h-indole-4-carboxylic acid 1h-indole-5-carbonitrile 1h-indole-5-carboxylic acid 1h-indole-6-carbonitrile 1h-indole-6-carboxylic acid 1h-indole-7-carbonitrile 1h-indole-7-carboxylic acid 1h-pyrrolo[2,3-b]pyridine-3-carbaldehyde 1h-pyrrolo[2,3-b]pyridine-5-carbaldehyde 2,3,4,5-tetrahydro-1h-pyrido[4,3-b]indole 2,3,4,9-tetrahydro-1h-pyrido[3,4-b]indole 2,3-dimethyl-1h-indole 2-(1,3,2-dioxaborolan-2-yl)-1-methyl-1h-indole 2-(1h-indol-1-yl)acetic acid 2-(1h-indol-3-yl)acetic acid 2-(1h-indol-3-yl)ethan-1-amine 2-(1h-indol-3-yl)ethan-1-ol 2-(2-methyl-1h-indol-3-yl)acetic acid 2-(4-fluorophenyl)-1h-indole 2-methyl-1h-indole-3-carbaldehyde 2-methyl-1h-pyrrolo[2,3-b]pyridine 3-(1-oxoisoindolin-2-yl)piperidine-2,6-dione 3-(1h-indol-3-yl)propanoic acid 3-(piperidin-4-yl)-1h-indole 3-iodo-1h-pyrrolo[2,3-b]pyridine 3-methyl-1h-indole 3h-indole 4-bromo-1h-indole 4-chloro-1h-indole 4-fluoro-1h-indole 4-fluoro-1h-pyrrolo[2,3-b]pyridine 4-fluoroindoline-2,3-dione 4-methoxy-1h-indole 4-methyl-1h-indole 4-nitro-1h-indole 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-indole 5-(benzyloxy)-1h-indole 5-bromo-1-methyl-1h-indole 5-chloro-1h-indole 5-chloro-1h-indole-2-carboxylic acid 5-chloro-1h-pyrrolo[2,3-b]pyridine 5-fluoro-1h-indole 5-fluoro-1h-pyrrolo[2,3-b]pyridine 5-fluoroindolin-2-one 5-methoxy-1h-indole 5-methoxy-2-methyl-1h-indole 5-methyl-1h-indole 5-nitro-1h-indole 6-(trifluoromethyl)-1h-indole 6-bromo-1-methyl-1h-indole 6-bromo-1h-indole 6-bromo-1h-pyrrolo[2,3-b]pyridine 6-chloro-1h-indole 6-chloro-1h-pyrrolo[2,3-b]pyridine 6-fluoro-1h-indole 6-methoxy-1h-indole 6-methyl-1h-indole 6-methyl-1h-pyrrolo[2,3-b]pyridine 6-nitro-1h-indole 7-bromo-1h-indole 7-bromoindoline-2,3-dione 7-chloro-1h-indole 7-fluoro-1h-indole 7-fluoro-1h-indole-2-carboxylic acid 7-methoxy-1h-indole 7-methyl-1h-indole 7-nitro-1h-indole 9h-pyrido[3,4-b]indole Benzo[cd]indol-2(1h)-one Ethyl 1h-indole-3-carboxylate Ethyl 5-chloro-1h-indole-2-carboxylate Ethyl 5-fluoro-1h-indole-2-carboxylate Ethyl 6-chloro-1h-indole-2-carboxylate Ethyl 7-chloro-1h-indole-2-carboxylate Methyl 1h-indole-3-carboxylate Methyl 1h-indole-4-carboxylate Methyl 1h-indole-5-carboxylate Methyl 1h-indole-6-carboxylate Methyl 1h-indole-7-carboxylate Methyl 2-(1h-indol-3-yl)acetate N-(2-(1h-indol-3-yl)ethyl)acetamide Spiro[indoline-3,4'-piperidin]-2-one Tert-butyl 1h-indole-1-carboxylate Tert-butyl 1h-pyrrolo[2,3-b]pyridine-1-carboxylate Tert-butyl 2-(1,3,2-dioxaborolan-2-yl)-1h-indole-1-carboxylate Tert-butyl 3-(hydroxymethyl)-1h-indole-1-carboxylate Tert-butyl 3-bromo-1h-indole-1-carboxylate Tert-butyl 3-iodo-1h-indole-1-carboxylate Tert-butyl 5-methoxy-1h-indole-1-carboxylate Tryptophan

By Key Group+−

Aminoindole Azaindole Benzoindole Benzyloxyindole Biindolinylidene Bromo-indole-carboxylate Bromo-indole-carboxylic acid Bromo-indole-carboxylic-acid Bromo-methyl-indole Bromoindole Chlorindole-carboxylic-acid Chloro-indole-carboxylate Chloro-methyl indole Chloroindole Cyanoindole Dihydroindolo Dimethyl-indole Dioxaborolan-indole Dioxaborolan-indole-carboxylate Fluorindole-carboxylic acid Fluorindole-carboxylic-acid Fluoro-indole-carboxylate Fluoroindole Fluoromethyl-indole Formyl-indole-carboxylate Formylindole Hydroxyindole Hydroxyisoindoline Hydroxymethy-indole-carboxylate Indol-amine Indol-methanamine Indol-methanol Indol-one Indole-boronic acid Indole-boronic acid/ester Indole-boronic-acid Indole-carbonitrile Indole-ethanol Indole-ethylamine Indole-hydrochloride Indole-hydroxyl Indolecarboxylate Indolecarboxylic Iodo-indole Isoindole Methoxy-indole-carboxylate Methoxy-methyl-indole Methoxyindole Methyl-indole-carboxylic-acid Methyl-nitro-indole Methylindole Nitro-indole-carboxylate Nitroindole Phenyl-indole Piperidine-indole Pyridinoindole Pyrimido-indole Trifluoromethyl-indole

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aromatic heterocycles benzofurans indolines other aromatic heterocycles piperazines Piperidines Pyrazoles Pyridines Pyrimidines pyrroles pyrrolidines pyrrolines

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alcohols aldehydes alkenyls amides amines aryls bromides carboxylic acid salts carboxylic acids Chiral building blocks chlorides esters ethers fluorinated building blocks hydrazides hydrazines hydroxylamines iodides ketones nitriles nitroes phenols sulfamides sulfides trifluoromethyls

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