85992-59-2

Upstream product

• 96694-00-7 1-methyl-3-trimethylsilylindole 
• 103-80-0 phenylacetyl chloride 
• 603-76-9 1-methylindole 
• 140-29-4 phenylacetonitrile 
• 3389-53-5 phenylacetylpyrrolidine 

Downstream Products

• 85992-56-9 1-(1-Methyl-1H-indol-3-yl)-2-phenyl-ethanone oxime 

Relevant academic research and scientific papers

New Friedel-Crafts strategy for preparing 3-acylindoles

A selective Friedel-Crafts acylation of indoles via an unusual cleavage of the amide C-N bond was achieved by triflic anhydride activation. This method offers rapid efficient access to high-biological-value 3-acylindoles, performs a series of scrupulous mechanistic studies and offers a strong courage that amide synthons can form new C-C bonds under transition-metal-free conditions.

Visible light-photocatalysed carbazole synthesis: Via a formal (4+2) cycloaddition of indole-derived bromides and alkynes

We successfully developed an unprecedented route to carbazole synthesis through a visible light-photocatalysed formal (4+2) cycloaddition of indole-derived bromides and alkynes. This novel protocol features extremely mild conditions, a broad substrate scope and high reaction efficiency.

A new methodology for functionalization at the 3-position of indoles by a combination of boron lewis acid with nitriles

We discovered that a reagent comprising a combination of PhBCl2 and nitriles was useful for syntheses of both 3-acylindoles and 1-(1H-indol-3-yl)alkylamine from indoles. The reaction proceeded selectively at the 3-position of indoles providing 3-acylindoles in moderate to high yields on treatment with the above reagent. Furthermore, the reaction provided the corresponding amine products in moderate to high yields after the intermediate imine was reduced by NaBH3CN. These reactions proceeded under mild conditions and are applicable to the formation of indoles functionalized at the 3-position.

Facile access to 3-acylindoles through palladium-catalyzed addition of indoles to nitriles: The one-pot synthesis of indenoindolones

A palladium-catalyzed addition of indoles to nitriles, leading to 3-acylindoles, was reported, and the scope of nitriles was investigated. The strategy described provides a more efficient and atom-economical alternative to indenoindolones. It was found that alkenyl, carbonyl, halogen, methoxy, and nitro groups on aryl nitriles, which could offer opportunities for further synthetic transformations, are all compatible with the conditions. N-unprotected indoles with electron-rich groups show excellent reactivity towards this addition reaction. Under the optimized conditions, an array of indenoindolones are obtained in synthetic useful yields from readily available indoles and nitriles in one pot. The results also show that both the electron-poor and electron-rich substituents could be introduced to indoles and nitriles and that the halogen atoms were compatible under the current conditions.

An New Method for the Synthesis of 3-Substituted Indoles by ipso-Substitution

Acylation of 3-(trimethylsilyl)-indole 1a with acylhalides 2 affords 3-acylindoles 4. 3-(Trimethylsilyl)-indoles 1a, b react with Michael-acceptors 5 and 8 in presence of Lewis acids to yield the 3-substituted indoles 6, 9, and 10.