14255-18-6

Usage

Physical State

Yellow solid.

Usage

Synthesis of various pharmaceuticals, agrochemicals, and dyes.

Optical Properties

Luminescent properties, making it valuable in the production of fluorescent dyes and materials.

Potential Health Benefits

Antioxidative and anti-inflammatory effects, making it a promising target for drug development in the future.

Upstream product

• 19005-93-7 1H-indol-2-ylcarboxaldehyde 
• 75-52-5 nitromethane 
• 24621-70-3 2-(hydroxymethyl)indole 
• 1477-50-5 Indole-2-carboxylic acid 
• 1202-04-6 indole-2-carboxylic acid methyl ester 
• 487-89-8 Indole-3-carboxaldehyde 

Downstream Products

• 496-42-4 1H-indole-2-ethanamine 
• 1304779-83-6 2-(1-benzyl-2,5-dimethyl-1H-pyrrol-3-yl)-1H-indole 
• 1304779-80-3 2-(1-benzyl-2,5-diphenyl-1H-pyrrol-3-yl)-1H-indole 
• 1304779-89-2 2-(1-benzyl-5-methyl-2-phenyl-1H-pyrrol-3-yl)-1H-indole 
• 1304779-94-9 3-(1-benzyl-2-methyl-5-phenyl-1H-pyrrol-3-yl)-1-(phenylsulfonyl)-1H-indole 
• 1304779-95-0 2-(1-benzyl-2-methyl-5-phenyl-1H-pyrrol-3-yl)-1H-indole 
• 1306669-86-2 (1S,2S)-2-benzyl-1-(nitromethyl)-1H-pyrrolo[1,2-a]indol-3(2H)-one 

Relevant academic research and scientific papers

Au(I)-Catalyzed Pictet-Spengler Reactions All around the Indole Ring

Au(I) complexes catalyze iso-Pictet-Spengler reactions. Ethylamine or methylamine chains were introduced at C2, C4, or the nitrogen atom of the indole ring, and the corresponding substrates were reacted in the presence of aldehydes and catalytic amounts of Au(I) complexes, leading to a variety of polycyclic scaffolds. Selectivity could be achieved in the course of a double iso-Pictet-Spengler reaction involving two successive aldehydes, leading to highly complex molecules.

A Novel Sc(OTf)3-Catalyzed (2+2+1)-Cycloannulation/Aza-Friedel–Crafts Alkylation Sequence toward Multicyclic 2-Pyrrolines

The rapid assembly of molecular complexity continues to be at the forefront of novel reaction development. In the pursuit of that goal, we herein report a novel Sc(OTf)3-catalyzed, one-pot multicomponent reaction that furnishes complex multicyclic 2-pyrrolines with excellent overall yields and perfect diastereocontrol. This process is based on our previously established (2+2+1)-cycloannulation of in situ generated 1-azaallyl cations, 1,3-dicarbonyls and primary amines. The newly formed and highly reactive aminal moiety is readily substituted with indoles and pyrroles both as external and internal π-nucleophiles to provide densely functionalized N-heterocycles with four new σ-bonds and two vicinal quaternary stereogenic centers. In addition, DFT calculations have been conducted to further characterize the intermediate 1-azaallyl cations.

An Enantio- and Diastereoselective Mannich/Pictet–Spengler Sequence To Form Spiro[piperidine-pyridoindoles] and Application to Library Synthesis

A new tandem strategy based on a Mannich/Pictet–Spengler sequence has been developed and applied to the synthesis of a new small library (14 examples) of privileged compounds based on the spiro[piperidine-pyridoindole] core. The sequence proceeds by a diastereoselective Pictet–Spengler cyclization after condensation of several tryptamine derivatives with three novel piperidin-4-ones containing the fluorinated substituents F, CF3and SF5. The piperidin-4-ones were synthesized from readily available starting materials by an enantioselective multi-component organocatalytic Mannich reaction.

One-pot organocatalytic asymmetric synthesis of 1H-pyrrolo[1,2a]indol-3(2H) -ones via a Michael-hemiaminalization-oxidation sequence

An efficient one-pot organocatalytic asymmetric synthesis of 1,2-cis-disubstituted 1H-pyrrolo[1,2a]indol-3(2H)-ones in moderate to good overall yields (49-68%) is presented. The Michael-hemiaminalization-oxidation sequence occurs with very high asymmetric

Synthesis of 2-and 3-indolylpyrroles via 1,3-dipolar cycloadditions of muenchnones and nitroalkenes

A series of 2-and 3-indolylpyrroles were generated via 1,3-dipolar cycloadditions between (2-nitrovinyl)indoles and symmetrical and unsymmetrical 1,3-oxazolium-5-olates (muenchnones). The Japan Institute of Heterocyclic Chemistry.

Synthese d'aryl nitronorbornenes par cycloaddition de Diels-Alder entre les aryl-nitroethylenes et le cyclopentadiene. Justification de la stereochimie et de la reactivite relative observees par la methode CNDO/II. Obtention d'aryl aminonorbornenes

Syntheses of numerous 2-aryl nitroethylenes (nitrostyrenes) have been optimized.The nitrostyrenes have been reacted with cyclopentadiene in Diels-Alder cycloadditions and the 3-aryl 2-nitronorbornenes obtained have been reduced into 3-aryl 2-aminonorbornenes.These compounds are potentially dopaminergic molecules.The stereochemistry of the adducts obtained in the Diels-Alder reaction has been determined by 1H nmr.The stereochemistry and the relative reactivity of the nitrostyrenes versus cyclopentadiene have been confirmed by theoretical calculations based on the CNDO/II method.