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• 3. Alkylation of amines with allylic alcohols and deep eutectic solvents as metal-free and green promoters
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• 4. Structures, dipole moments and excited state lifetime of isolated 4-cyanoindole in its ground and lowest electronically excited singlet states
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• 5. Copper-catalyzed synthesis of indolyl diketones via C–H oxidation/diacylation of indoles with arylglyoxal hydrates
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1H-indole-4-carbonitrile (CAS No. 16136-52-0): A Comprehensive Overview

1H-indole-4-carbonitrile, a heterocyclic compound with the CAS registry number 16136-52-0, has garnered significant attention in the fields of organic chemistry, pharmacology, and materials science. This compound is characterized by its indole ring system, which is a bicyclic structure consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. The presence of a nitrile group (-CN) at the 4-position of the indole ring imparts unique electronic and structural properties to this molecule, making it a versatile building block in chemical synthesis.

The synthesis of 1H-indole-4-carbonitrile has been extensively studied, with various methodologies reported in the literature. One common approach involves the condensation of o-amino phenylacetonitrile with aldehydes or ketones under appropriate conditions. This reaction typically proceeds through a nucleophilic attack mechanism, facilitated by the electron-rich nitrogen atom in the indole system. Recent advancements in catalytic systems and green chemistry have further optimized these synthetic routes, reducing environmental impact and improving yield.

1H-indole-4-carbonitrile exhibits interesting electronic properties due to the conjugation between the indole ring and the nitrile group. The nitrile moiety acts as an electron-withdrawing group, which can influence the reactivity of the molecule in various chemical transformations. This property has made 1H-indole-4-carbonitrile a valuable substrate for further functionalization, such as nucleophilic addition, cycloaddition reactions, and cross-coupling reactions. These reactions are pivotal in drug discovery and materials synthesis.

In recent years, 1H-indole-4-carbonitrile has been explored as a potential lead compound in drug development. Its structural similarity to known bioactive molecules makes it an attractive candidate for studying interactions with biological targets such as enzymes and receptors. For instance, researchers have investigated its potential as an inhibitor of kinase enzymes, which are implicated in various diseases including cancer and inflammatory disorders. Preliminary studies have shown promising results, highlighting its potential for further optimization into therapeutic agents.

Beyond pharmacology, 1H-indole-4-carbonitrile has found applications in materials science. Its ability to form stable coordination complexes with metal ions has led to its use in designing novel materials for catalysis and sensing applications. For example, metalloporphyrins derived from indole derivatives have been employed as catalysts in organic synthesis due to their high stability and selectivity.

Recent advancements in computational chemistry have provided deeper insights into the electronic structure and reactivity of 1H-indole-4-carbonitrile. Quantum mechanical calculations have revealed that the nitrile group significantly alters the electron density distribution across the molecule, enhancing its reactivity towards electrophilic species. These findings have been corroborated by experimental studies, which have demonstrated improved yields in reactions involving this compound.

In conclusion, 1H-indole-4-carbonitrile (CAS No. 16136-52-0) stands out as a versatile and multifaceted compound with applications spanning organic synthesis, pharmacology, and materials science. Its unique structural features and electronic properties continue to inspire innovative research directions, underscoring its importance as a key player in modern chemistry.

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